- Incorporation of nanosized ZnWO4 and Fe3O4 on graphitic carbon nitride to fabricate a novel, highly active magnetically recoverable catalyst in Claisen–Schmidt condensation
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Herein we outline a facile and viable approach for successful anchoring of ZnWO4 and Fe3O4 nanoparticles on graphitic carbon nitride (g-C3N4) through ultrasonication and microwave irradiation. The as-synthesised nanocomposite, g-C3N4–Fe3O4–ZnWO4, was characterised using Fourier transmission infrared spectroscopy, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy, vibrating-sample magnetometry, and X-ray photoelectron spectroscopy techniques. The nanocomposite exhibited appreciable catalytic performance in the Claisen–Schmidt condensation reaction between benzaldehyde and acetone producing dibenzalacetone with excellent yields. The as-prepared catalyst demonstrated excellent magnetically recyclable property for seven successive runs. The presence of g-C3N4 in the nanocomposite g-C3N4–Fe3O4–ZnWO4 played a significant role in promoting the catalytic activity due to its inherent basic nature and efficient grafting of the substrates onto the g-C3N4 sheets.
- Paul, Arijita,Devi, Meghali,Dhar, Siddhartha Sankar
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- Synthesis, characterization, DFT and molecular docking studies for novel 1,5-diphenylpenta-1,4-dien-3-one O-benzyl oximes
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The main objectives of this study are: (a) to synthesize novel 1,5-diphenylpenta-1,4-dien-3-one O-benzyl oximes in an efficient way, (b) to investigate the synthesized molecules computationally via DFT calculations, (c) to compare computationally obtained data with experimental results and (d) to perform molecular docking calculations for the newly synthesized compounds and heat shock protein HSP90A N-terminal domain to determine the binding affinities of the investigated molecules and to reveal possible receptor–ligand interactions. In the first part of the study, syntheses and characterizations of the investigated compounds have been carried out. In this part, the target compounds have been synthesized and characterized successively. In the synthesis of target compounds from corresponding oximes, ultrasound has been used alternatively and results showed that the usage of ultrasound considerably increases the reaction rate and the efficiency. In the second part, detailed density functional theory calculations have been performed on the investigated compounds with the use of Becke, three-parameter, Lee–Yang–Parr hybrid functional and various basis sets. In this part, geometry optimizations, frequency analyses, NMR spectral analyses, frontier molecular orbital calculations, and molecular electrostatic potential map calculations have been performed. In NMR spectral analyses, both continuous set of gauge transformations (CSGT) and gauge-independent atomic orbital (GIAO) methods have been used and the obtained results with the use of various basis sets have been compared. Results showed that in NMR calculations, GIAO method is more successful than CSGT method and can provide satisfactory results even with small basis sets. In the third part of the study, molecular docking calculations have been performed on the investigated compounds and HSP90A N-terminal domain. Results showed that investigated molecules show a good binding affinity for HSP90A N-terminal domain. The binding affinities were found to be in the range of ? 8.7 to ? 10.1?kcal/mol.
- Erdogan, Taner
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- Synthesis, characterization and evaluation of topical antiinflammatory activity of dimethyl 4-oxo-2,6-diphenylcyclohexane-1,1-dicarboxylate
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An attempt was made to synthesize a topical preparation of an active compound that has a potent antiinflammatory activity. Dimethyl 4- oxo-2,6-diphenylcyclohexane-1,1-dicarboxylate (II) was prepared by aldol condensation of benzaldehyde and acetone followed by Michael addition of dimethyl malonate. The optimum concentration of the compound was determined by comparing the antiinflammatory effect of ointment preparations at different concentrations. The antiinflammatory effects were studied by using carrageenan-induced paw edema method in rat and xylene induced rat ear edema. Good effect was observed with ointment containing 4 % and 5 % of the compound II concentration. The results showed that the drug had an obvious antiinflammatory effect as an external preparation and the activity is comparable to that of the standard ointment.
- Al Ugla, Mazin Nadhim Mousa
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- Antibacterial activity of a new monocarbonyl analog of curcumin MAC 4 is associated with divisome disruption
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Curcumin (CUR) is a symmetrical dicarbonyl compound with antibacterial activity. On the other hand, pharmacokinetic and chemical stability limitations hinder its therapeutic application. Monocarbonyl analogs of curcumin (MACs) have been shown to overcome these barriers. We synthesized and investigated the antibacterial activity of a series of unsymmetrical MACs derived from acetone against Mycobacterium tuberculosis and Gram-negative and Gram-positive species. Phenolic MACs 4, 6 and 8 showed a broad spectrum and potent activity, mainly against M. tuberculosis, Acinetobacter baumannii and methicillin-resistant Staphylococcus aureus (MRSA), with MIC (minimum inhibitory concentration) values ranging from 0.9 to 15.6 μg/mL. The investigation regarding toxicity on human lung cells (MRC-5 and A549 lines) revealed MAC 4 was more selective than MACs 6 and 8, with SI (selectivity index) values ranging from 5.4 to 15.6. In addition, MAC 4 did not demonstrate genotoxic effects on A549 cells and it was more stable than CUR in phosphate buffer (pH 7.4) for 24 h at 37 °C. Fluorescence and phase contrast microscopies indicated that MAC 4 has the ability to disrupt the divisome of Bacillus subtilis without damaging its cytoplasmic membrane. However, biochemical investigations demonstrated that MAC 4 did not affect the GTPase activity of B. subtilis FtsZ, which is the main constituent of the bacterial divisome. These results corroborated that MAC 4 is a promising antitubercular and antibacterial agent.
- Polaquini, Carlos R.,Marques, Beatriz C.,Ayusso, Gabriela M.,Mor?o, Luana G.,Sardi, Janaína C.O.,Campos, Débora L.,Silva, Isabel C.,Cavalca, Lúcia B.,Scheffers, Dirk-Jan,Rosalen, Pedro L.,Pavan, Fernando R.,Ferreira, Henrique,Regasini, Luis O.
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- Bu4NHSO4-Catalyzed Direct N-Allylation of Pyrazole and its Derivatives with Allylic Alcohols in Water: A Metal-Free, Recyclable and Sustainable System
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Allylic amines are valuable and functional building blocks. Direct N-allylation of pyrazole and its derivatives as an atom economic strategy to provide allylic amines has been achieved only using commercial Bu4NHSO4 as the metal-free catalyst and water as the solvent without any additives. 11–93% isolated yields were obtained for the N-allylation of pyrazole and its derivatives with allylic alcohols. Bu4NHSO4 could be reused for six times by simple extraction nearly without loss of catalytic activity and was also suitable for a gram-scale production. The reaction of allylic ether and pyrazole did not occur to give the desired product indicated that allylic ether was not the active intermediate in the pathway. Density functional theory (DFT) calculations reveal that there are hydrogen bonding effects among substrates, solvent and catalyst, especially the one formed between allylic alcohol and H2O. Control experiments in different protic solvents further demonstrate the intermolecular hydrogen bonding of allylic alcohol and water. (Figure presented.).
- Zhuang, Hongfeng,Lu, Nan,Ji, Na,Han, Feng,Miao, Chengxia
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supporting information
p. 5461 - 5472
(2021/09/29)
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- Application of monocarbonyl curcumin compound in preparation of medicine for preventing and treating periodontitis
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The invention belongs to the technical field of medicines, and particularly relates to application of a specific monocarbonyl curcumin analogue in preparation of a medicine for preventing and treating periodontitis. Experiments prove that the monocarbonyl curcumin analogues not only can play a better anti-oxidation protection role by activating an Nrf2/HO-1 signal channel, but also can play an anti-inflammatory role by inhibiting release of inflammatory factors TNF alpha and IL1-beta, so that the monocarbonyl curcumin analogues have a remarkable prevention and treatment effect on rat periodontitis, have good potential value and significance for prevention and treatment of periodontitis, and have a good research and development prospect.
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Paragraph 0024-0026; 0028
(2021/06/22)
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- Stereoselective synthesis, spectral characterization, docking and biological screening of coumarin derivatives
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The compounds being synthesized in present research are chiral in nature so for getting enantiopure compounds, stereoselective synthesis was carried out by organocatalysis. The importance of enantiopure compounds can not be overstated because the living systems are chiral in nature and response of enantiomers can be very different in living systems. The organocatalysed synthesis was accumplished using 4-hydroxycoumarin and variously substituted dibenzylideneacetones as reactants and the organocatalyst being used was 9-amino-9-deoxyepiquinine. The range of enantioselectivity achieved was 24-95%. The synthesized compounds were characterized by UV, IR, 1H NMR, 13C NMR, EIMS, UVCD, VCD and Chiral HPLC. The major focus of this research was to develop anticoagulant compounds and therefore the molecular docking studies were carried out with crystal structure of vitamin k epoxide reductase (3kp9) and then screened for in-vitro anticoagulant activity by using warfarin as positive control. Out of six synthesized compounds, four compounds (1,2,5,6) have shown greater binding affinity with 3kp9 than warfarin. In in-vitro anticoagulant studies, all compounds showed improved IC50 values than warfarin. Besides anticoagulant activity, antimocrobial activities were also carried out with six different strains of bacteria and fungi. Compound (5) showed 79% inhibition against Bacillus subtillis and 62 % inhibition against Staphylococcus aureus.
- Afzal, Zakia,Nadeem, Humaira,Rashid, Naghmana
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p. 330 - 341
(2021/07/19)
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- Synthesis of Ketones by C?H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions
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A method for the synthesis of ketones from aldehydes and boronic acids via a transition-metal-free C?H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive the simultaneous activation of the boronic acid as a boronate and the activation of the C?H bond of the aldehyde as an iminium species that triggers the key C?C bond-forming step via an intramolecular migration from boron to carbon. These findings constitute a practical, scalable, and operationally straightforward method for the synthesis of ketones.
- Roscales, Silvia,Csáky, Aurelio G.
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supporting information
p. 8728 - 8732
(2021/03/16)
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- Monofunctional curcumin analogues: evaluation of green and safe developers of latent fingerprints
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Fingerprint development is one of the most useful techniques in forensic investigation. The powder method is widely used, as it consists of a non-destructive testing. However, some of the powders commonly used are toxic and dangerous to human health. In this sense, monofunctional analogues of curcumin (3a–e) are proposed as novel coloring powders for the development of latent fingerprints. Granulometric and scanning electron microscopy analysis were performed for a better understanding of the interaction between developers and substrates. The best results for the development of fingerprints were obtained with compound (1E,4E)-1,5-di-p-tolylpenta-1,4-dien-3-one (3b). Development with this compound was specific and allowed detection both from male and female donors. Also, in an in vitro experiment, compound 3b presented low cytotoxicity in a mammalian cell line. Based on that, a novel alternative for latent fingerprint developers was proposed.
- Pacheco, Bruna S.,Da Silva, Caroline C.,Da Rosa, Bruno N.,Mariotti, Kristiane C.,Nicolodi, Caroline,Poletti, Taís,Segatto, Natália V.,Collares, Tiago,Seixas, Fabiana K.,Paniz, Oscar,Carre?o, Neftali Lenin Vilarreal,Pereira, Claudio M. P.
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p. 3119 - 3129
(2021/02/26)
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- Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids
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Ionic Liquids (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs using Electrospray Ionization Mass Spectrometry (ESI-MS). We have synthesized four hydrophilic ILs (1–4) and investigated their aggregation behavior and its impact on catalytic activity in Carbon-Carbon bond formation (Knoevenagel and Claisen-Schmidt condensation). Here, we show that the aggregation behavior of ILs depends on the type and nature of cation and anion. ESI-MS (?ve) spectra reveals two different type of aggregation i.e. [CnAn+1]? & [A2 + H+]?. We have found that catalytic activity increases with increased [CnAn+1]? supramolecular aggregation. Consequently, highest yield of products obtained in ILs which show decreased anion-anion aggregation [A2 + H+]? abundance in ESI-MS. We anticipate our results to be a starting point for the establishment of desired ILs for organic synthesis.
- Muhammad, Shoaib,Javed, Muhammad Naveed,Ali, Firdous Imran,Bari, Ahmed,Hashmi, Imran Ali
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- Second harmonic generation in pyrazoline derivatives of dibenzylideneacetones and chalcone: A combined experimental and theoretical approach
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In this work, we investigate theoretically and experimentally second harmonic generation (SHG) in three pyrazoline compounds, being two derivatives of dibenzylideneacetone (DBA) (C23H20N2 and C25H24N2O2) and one derivative of chalcone (C21H18N2). The compounds were synthesized after two steps employing a Claisen-Schmidt condensation followed by an addition-elimination reaction with phenylhydrazine. All compounds were characterized using NMR, FT-IR, UV-Vis, and XRD. We calculated the first-order hyperpolarizabilities of these molecules using program packages based on the time-dependent Hartree-Fock (TDHF) and density functional theory (DFT). SHG was characterized by Kurtz and Perry's powder method. We observed that these organic crystals present SHG efficiencies up to 5 times larger than the KDP, and we associated these values to their molecular structure and crystalline arrangements. The values obtained experimentally and theoretically evidence that these compounds have good potential for application in electronic devices based on second-order nonlinear responses.
- de Araújo, Raiane Sodré,de Alcantara, Aline Moreira,Abeg?o, Luis M.G.,de Souza, Yago Pereira,Brand?o Silva, Ant?nio Carlos,Machado, Rogério,Joatan Rodrigues, José,Rodriguez Pliego, Josefredo,d'Errico, Francesco,Siqueira Valle, Marcelo,de Alencar, Márcio André Rodrigues Cavalcanti
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- Some 1,3,5-trisubstituted pyrazoline derivatives targeting breast cancer: Design, synthesis, cytotoxic activity, EGFR inhibition and molecular docking
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Different 1,3,5-trisubstituted pyrazoline derivatives 2a-c, 3-c, 4a-f, 6a-c, 7a-f and 8a-d were prepared via condensation reaction of the appropriate chalcone 1a-c or 5a-c with various hydrazine derivatives. All compounds were screened for their cytotoxicity against breast MCF-7 cancer cell line and the normal fibroblasts WI-38. Thirteen compounds 2a, 3a, 3c, 4a-d, 6c, 7d, 7e, 8b, 8d and 8f revealed promising cytotoxicity against MCF-7 compared to the reference standard staurosporine and they were safe to the normal fibroblasts WI-38. In addition, compounds 3c, 6c, 7d, 8b and 8d elicited higher cytotoxicity than erlotinib and exhibited promising EGFR inhibitory activity at submicromolar level comparable to that of erlotinib except for compound 8b that may exert its cytotoxicity via another mechanism besides EGFR inhibition. Molecular docking of 3c, 6c, 7d, 8b and 8d in the active site of EGFR confirmed the obtained results.
- El Kerdawy, Ahmed M.,El-Ansary, Dina Y.,George, Riham F.,Kandeel, Manal
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supporting information
(2020/03/31)
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- Synthesis of tetracyclic oxindoles and evaluation of their α-glucosidase inhibitory and glucose consumption-promoting activity
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A series of tetracyclic oxindole derivatives was synthesized by asymmetric 1, 3-dipole reaction in 2–4 steps in 57–86% overall yields. These compounds were evaluated for α-glucosidase inhibitory and glucose consumption-promoting activity in vitro. Compound 4l competitively and reversibly inhibited α-glucosidase (IC50 = 3.64 μM) with activity 14-fold higher than that of acarbose. Docking analysis substantiated these findings. In addition, compound 4l exhibited significant glucose consumption promoting activity at 1 μM.
- Dodd, Robert H.,Hao, Lei,Ma, Ying,Ma, Yujiao,Sun, Hua,Yu, Peng,Zhang, Xinying,Zhang, Yinan,Zhao, Lianbo
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supporting information
(2020/05/27)
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- Organocatalytic asymmetric vinylogous 1,4-addition of α,α-Dicyanoolefins to chalcones under a bio-based reaction media: Discovery of new Michael adducts with antiplasmodial activity
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The organocatalysed asymmetric vinylogous Michael addition of α,α-dicyanoolefins to α,β-unsaturated aldehydes and ketones have been reported in the last decade, however, chalcones have been poorly explored. Moreover, a considerable part of the publications in this theme still employs undesirable solvents, such as toluene and THF, with concerns related to health and environmental safety. We report herein the use of a bifunctional catalyst derived from a Cinchona alkaloid to perform the enantio- and diastereoselective Michael addition of α,α-dicyanoolefins to chalcones using 2-MeTHF as solvent. The Michael adducts were obtained in moderate to good yields and were evaluated for their antiplasmodial and cytotoxic activity.
- Martelli, Lorena S.R.,Vieira, Lucas C.C.,Paix?o, Márcio W.,Zukerman-Schpector, Julio,de Souza, Juliana O.,Aguiar, Anna Caroline C.,Oliva, Glaucius,Guido, Rafael V.C.,Corrêa, Arlene G.
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supporting information
p. 3530 - 3542
(2019/05/24)
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- Exploration of synthetic antioxidant flavonoid analogs as acetylcholinesterase inhibitors: an approach towards finding their quantitative structure–activity relationship
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The binding interactions between acetylcholinesterase (AChE) and a series of antioxidant flavonoid analogs were studied by fluorescence spectroscopic assay. The present study incorporated different classes of naturally occurring and synthetic flavonoid compounds like flavones, isoflavones, and chalcones as well as a few standard antioxidants. The AChE inhibitory (AChEI) activity of these compounds was further analyzed using in silico techniques, namely pharmacophore mapping, quantitative structure–activity relationship (QSAR) analysis, and molecular docking studies. We have also compared the AChE inhibitory and radical scavenging antioxidant activities of these compounds. Both the AChE inhibitory and antioxidant activities of these compounds were found to be highly dependent on their structural patterns. However, it was observed that, in general, flavones are comparatively better AChE inhibitors as well as antioxidants compared to chalcones. [Figure not available: see fulltext.].
- Karmakar, Abhijit,Ambure, Pravin,Mallick, Tamanna,Das, Sreeparna,Roy, Kunal,Begum, Naznin Ara
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p. 723 - 741
(2019/04/17)
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- Intermolecular Multiple Dehydrogenative Cross-Couplings of Ketones with Boronic Acids and Amines via Copper Catalysis
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An efficient and versatile oxidative coupling reaction was developed for the synthesis of valuable β-functionalized unsaturated ketones and meta-substituted phenols. In the case of intramolecular reactions, achieving rapid molecular complexity through multiple dehydrogenative couplings is already a well-established strategy. Herein, we report an intermolecular multiple dehydrogenative coupling between ketones and nucleophilic amines or boronic acids using inexpensive copper(I) oxide as a catalyst. This method provides a facile access to highly desirable chemical products such as α,β-unsaturated ketones, enaminones, and synthetically relevant meta-substituted phenols. (Figure presented.).
- Wang, Tianzhang,Chen, Guowei,Lu, Yu-Jing,Chen, Qian,Huo, Yanping,Li, Xianwei
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supporting information
p. 3886 - 3892
(2019/07/19)
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- Basic Anion-Exchange Resin-Catalyzed Aldol Condensation of Aromatic Ketones with Aldehydes in Continuous Flow
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A general method for the aldol condensation of aromatic ketones with aldehydes was developed under continuous-flow conditions using a commercially available, strongly basic anion-exchange resin (A26) as catalyst. This procedure, in addition to exhibiting a wide substrate scope, promoted carbon-carbon bond formation under mild conditions using a quasi-stoichiometric ratio of starting reagents with good to excellent yields, thereby forming a limited amount of waste and allowing the process to be applied to sequential-flow systems. A proof of concept was developed in the first fully heterogeneously catalyzed two-step flow synthesis of donepezil, which is a blockbuster commercial anti-Alzheimer's drug.
- Laroche, Benjamin,Saito, Yuki,Ishitani, Haruro,Kobayashi, Shū
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supporting information
p. 961 - 967
(2019/05/02)
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- Synthesis of 4,5,6,7-tetrahydrobenzoxazol-2-ones by a highly regioselective Diels-Alder cycloaddition of exo-oxazolidin-2-one dienes with chalcones
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The synthesis of novel of 4,5,6,7-tetrahydrobenzoxazol-2-ones is herein reported. They were obtained in moderate to good yields by a highly regio- and stereoselective Diels-Alder cycloaddition of N-substituted exo-oxazolidin-2-one dienes with chalcones or bis-chalcones as dienophiles.
- Mastachi-Loza, Salvador,Ramírez-Candelero, Tania I.,Tapia-Bustamante, Asenet,González-Romero, Carlos,Díaz-Torres, Eduardo,Tamariz, Joaquín,Toscano, Rubén A.,Fuentes-Benítes, Aydeé
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supporting information
p. 1370 - 1374
(2019/04/30)
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- A Broad-Spectrum Synthesis of Tetravinylethylenes
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The first general synthesis of compounds of the tetravinylethylene (TVE) family is reported. Ramirez-type dibromo-olefination of readily accessible penta-1,4-dien-3-ones generates 3,3-dibromo[3]dendralenes, which undergo twofold Negishi, Suzuki–Miyaura or Mizoroki–Heck reactions with a wide variety of olefinic coupling partners. This route delivers a broad range of unsymmetrically substituted tetravinylethylenes with up to three different alkenyl substituents attached to the central C=C bond. The extensive scope of the approach is demonstrated by the preparation of the first higher order oligo-alkenic through-conjugated/cross-conjugated hybrid compounds. An unsymmetrically substituted TVE is shown to undergo a domino electrocyclization–cycloaddition with high site-selectivity and diastereoselectivity, thereby demonstrating the substantial synthetic potential of substituted TVEs for controlled, rapid structural complexity generation.
- Horvath, Kelsey L.,Newton, Christopher G.,Roper, Kimberley A.,Ward, Jas S.,Sherburn, Michael S.
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supporting information
p. 4072 - 4076
(2019/03/22)
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- Antiparasitic activity of synthetic curcumin monocarbonyl analogues against Trichomonas vaginalis
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Trichomoniasis is a parasitic infection caused by Trichomonas vaginalis and it is considered to be the most common non-viral sexually transmitted infection in the world. Since the 1960s, nitroimidazoles such as metronidazole are the drugs of choice for the treatment of trichomoniasis, but many adverse effects and allergic reactions may result from their use. Reports of metronidazole-resistant infections also highlight the importance for the search of new anti-T. vaginalis agents. Considering this, herein we report the anti-T. vaginalis evaluation of 21 synthetic monocarbonyl analogues of curcumin, which itself has been reported to possess antiparasitic potential. From the in vitro analysis of the synthetic molecules, untreated trophozoites, and metronidazole at 100 μM, it was observed that three curcumin analogues (3a, 3e, and 5e) exhibited anti-T. vaginalis activity comparable to metronidazole (no significant statistical difference). Optimal antiparasitic concentrations were determined to be 80 μM and 90 μM for propanone derivatives 3a and 3e, respectively, and 200 μM for cyclohexanone derivative 5e. Kinetic growth curves showed that, after 24 h, the trophozoites were completely inhibited. At the tested concentrations, natural curcumin did not significantly inhibit the growth of trophozoites, therefore demonstrating that the designed synthetic molecules not only have better chemical stability, but also higher anti-T. vaginalis potential. Cytotoxicity analysis, performed on VERO cells, demonstrated low, moderate and high cytotoxic effects for analogues 3e, 5e and 3a, respectively. This study suggests that these analogues possess chemical features of interest to be further explored as alternatives for the treatment of trichomoniasis.
- Carapina da Silva, Caroline,Pacheco, Bruna Silveira,das Neves, Raquel Nascimento,Dié Alves, Mirna Samara,Sena-Lopes, ?ngela,Moura, Sidnei,Borsuk, Sibele,de Pereira, Claudio Martin Pereira
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p. 367 - 377
(2019/01/03)
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- Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties
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The three-component reaction between alkyl- or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro-m-terphenyl derivatives containing β-alkylamino- or β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.
- Rocchi, Damiano,González, Juan F.,Gómez-Carpintero, Jorge,González-Ruiz, Víctor,Martín, M. Antonia,Sridharan, Vellaisamy,Menéndez, J. Carlos
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p. 722 - 731
(2018/10/20)
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- Gram-scale preparation of dialkylideneacetones through Ca(OH)2-catalyzed Claisen-Schmidt condensation in dilute aqueous EtOH
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A synthetic method of dialkylideneacetones has been developed. Compared with known protocols, the method employed catalytic Ca(OH)2 as the cheap, mild base catalyst and dilute aqueous EtOH (20%, v/v) as the green and safe solvent. The procedure was easily operated: In most cases, the product could be isolated by a simple filtration, and purified by washing with water. This paper provided experimental details of the reactions, which could be applied in gram-scale synthesis and should be a very reliable and practical protocol to prepare these useful compounds in laboratory and at the industrial level.
- Zhang, Hao,Han, Mengting,Yang, Chenggen,Yu, Lei,Xu, Qing
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- Iron(iii)-catalyzed selective N-O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from: N -vinyl-α,β-unsaturated ketonitrones
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An iron(iii)-catalyst controlled cyclization and selective N-O bond cleavage of N-vinyl-α,β-unsaturated nitrones has been achieved under mild conditions to access tetrasubstituted pyridines and 3,5-disubstituted isoxazolines in moderate to good yields. The tetrasubstituted pyridines were afforded with FeCl3 as a catalyst while using FeCl3·6H2O combined with 1,10-phenanthroline delivered isoxazolines. The regioselectivity for cyclization of styrenyl groups in N-vinyl-α,β-unsaturated nitrones was completely different during the formation of pyridines and isoxazolines. A rational mechanism for the formation of pyridines and isoxazolines was proposed based on the further control experimental studies. The isoxazolines can be converted to a novel bidentate N-ligand over four steps and an epoxypyridine scaffold was obtained from N-vinyl nitrone when copper(ii) acetate in combination with the prepared bidentate N-ligand was used.
- Chen, Chun-Hua,Wu, Qing-Yan,Wei, Cui,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
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supporting information
p. 2722 - 2729
(2018/06/29)
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- Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
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Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose-response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues.
- Deck, Lorraine M.,Hunsaker, Lucy A.,Vander Jagt, Thomas A.,Whalen, Lisa J.,Royer, Robert E.,Vander Jagt, David L.
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p. 854 - 865
(2017/12/13)
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- ACI/EG eutectic mixture mediated synthesis, characterization and: In vitro osteoblast differentiation assessment of spiropyrrolo[1,2- b] isoquinoline analogues
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An eco-friendly acetylcholine iodide-ethylene glycol (ACI/EG) deep eutectic mixture mediated green protocol has been developed for the synthesis of hitherto unexplored multi-functionalized linear tricyclic spiropyrrolo[1,2-b]isoquinoline analogues. The effects of the synthesized compounds on the osteoblast differentiation of hBMSC-TERT cell lines were investigated and promising results were observed with significant IC50 values. In addition, molecular modeling simulations were also performed with the 3D structure of BMP-2 to reveal binding interactions and orientations of highly potent spiropyrrolo[1,2-b]isoquinoline analogues.
- Periyasami, Govindasami,Arumugam, Natarajan,Rahaman, Mostafizur,Kumar, Raju Suresh,Manikandan, Muthurangan,Alfayez, Musaad A.,Premnath, Dhanaraj,Aldalbahi, Ali
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p. 16303 - 16313
(2018/05/22)
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- Design, in silico and in?vitro evaluation of curcumin analogues against Plasmodium falciparum
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The polyphenolic compound curcumin has been reported for its antimalarial properties in various scientific studies. Plasmodium falciparum ATP6, the parasite orthologue of mammalian sarcoplasmic Ca2+ ATPase (SERCA) has been identified as a key molecular target of both artemisinin and curcumin. The work was thereby undertaken to study the anti-malarial properties of two different series of curcumin analogues based on their docking interactions with PfATP6 and correlating the results with their anti-malarial activity. The compounds were designed retaining similar functional groups as that of the parent curcumin nucleus while incorporating changes in the carbon chain length, unsaturated groups and the number of ketone groups. The compounds (1E, 4E)-1,5-bis(4-methylphenyl)penta-1,4-dien-3-one (CD-9), (1E, 4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one (CD-8) and (E)-1,3-bis(4-hydroxylphenyl)prop-2-en-1-one (CD-1) showed IC50 values of 1.642?μM, 1.764?μM and 2.59?μM in 3D7 strain and 3.039?μM, 7.40?μM and 11.3?μM in RKL-2 strain respectively. Detailed structure-activity relationship studies of the compounds showed that CD-9 and CD-8 had a common hydrophobic interaction with the residue Leu268 of the PfATP6 protein and has been postulated through our study to be the reason for their antimalarial activity as seen after corroborating the results with the in?vitro study. The study provided valuable insight about the ligand-protein interaction of the various functional groups of curcumin and its analogues against the PfATP6 protein and their importance in imparting antimalarial action.
- Dohutia, Chandrajit,Chetia, Dipak,Gogoi, Kabita,Sarma, Kishore
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- Potent and Selective Inhibitors of Trypanosoma cruzi Triosephosphate Isomerase with Concomitant Inhibition of Cruzipain: Inhibition of Parasite Growth through Multitarget Activity
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Triosephosphate isomerase (TIM) is an essential Trypanosoma cruzi enzyme and one of the few validated drug targets for Chagas disease. The known inhibitors of this enzyme behave poorly or have low activity in the parasite. In this work, we used symmetrical diarylideneketones derived from structures with trypanosomicidal activity. We obtained an enzymatic inhibitor with an IC50value of 86 nm without inhibition effects on the mammalian enzyme. These molecules also affected cruzipain, another essential proteolytic enzyme of the parasite. This dual activity is important to avoid resistance problems. The compounds were studied in vitro against the epimastigote form of the parasite, and nonspecific toxicity to mammalian cells was also evaluated. As a proof of concept, three of the best derivatives were also assayed in vivo. Some of these derivatives showed higher in vitro trypanosomicidal activity than the reference drugs and were effective in protecting infected mice. In addition, these molecules could be obtained by a simple and economic green synthetic route, which is an important feature in the research and development of future drugs for neglected diseases.
- Aguilera, Elena,Varela, Javier,Birriel, Estefanía,Serna, Elva,Torres, Susana,Yaluff, Gloria,de Bilbao, Ninfa Vera,Aguirre-López, Beatriz,Cabrera, Nallely,Díaz Mazariegos, Selma,de Gómez-Puyou, Marieta Tuena,Gómez-Puyou, Armando,Pérez-Montfort, Ruy,Minini, Lucia,Merlino, Alicia,Cerecetto, Hugo,González, Mercedes,Alvarez, Guzmán
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supporting information
p. 1328 - 1338
(2016/07/20)
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- Mechanistically Inspired Route toward Hexahydro-2H-chromenes via Consecutive [4 + 2] Cycloadditions
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Utilizing two robust C-C bond-forming reactions, the Baylis-Hillman reaction and the Diels-Alder reaction, we report a highly enantio-, regio-, and diastereoselective synthesis of hexahydro-2H-chromenes via two sequential [4 + 2] cycloadditions. These tandem and formal cycloadditions have also been performed as a "one-pot" sequence to access the corresponding heterocycles constituting up to five contiguous stereocenters in excellent yields and stereoselectivity.
- Ashtekar, Kumar Dilip,Ding, Xinliang,Toma, Edmond,Sheng, Wei,Gholami, Hadi,Rahn, Christopher,Reed, Paul,Borhan, Babak
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supporting information
p. 3976 - 3979
(2016/08/30)
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- Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids
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In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1,ω-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class.
- Roman, Bart I.,De Ryck, Tine,Verhasselt, Sigrid,Bracke, Marc E.,Stevens, Christian V.
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p. 1027 - 1031
(2015/02/19)
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- TRPV-1 RECEPTOR ANTAGONIST COMPOUND DERIVED FROM 1,3,4-THIADIAZOLE ALKYLAMIDES AND CHALCONES
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This technology encompasses compounds derived from 1, 3, 4-thiadiazole alkylamides and chalcone, which inhibit the activation of the TRPV-1 receptor using capsaicin and temperature. Also disclosed is the use of these compounds in the treatment of diseases with TRPV-1 overexpression, such as chronic pain.
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Paragraph 0047
(2015/11/11)
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- Chemoselective biohydrogenation of α,β- and α,β,γ,δ-unsaturated ketones by the marine-derived fungus Penicillium citrinum CBMAI 1186 in a biphasic system
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To broaden the range of applicability of a reduction reaction mediated by the marine fungal strain Penicillium citrinum CBMAI 1186 to organic chemical processes, the ability of whole mycelia to grow in biphasic mixtures with organic solvents was tested with acetone, ethyl acetate, n-butanol, dichloromethane, n-hexane and toluene. n-Hexane was the least toxic solvent according to the amount of mycelial mass grown in an artificial sea water medium mixed with each solvent. Therefore, whole hyphae of P. citrinum CBMAI 1186 were used as biocatalysts in the chemoselective biotransformation of the carbon-carbon double bond in α,β-, di-α,β-, and mono-α,β,γ,δ-unsaturated ketones (3a, 3c-f) in a biphasic system of phosphate buffer and n-hexane (9:1). Only the di-α,β,γ,δ-unsaturated ketone (3b) was not biocatalyzed under these conditions. In general, there were good conversions of saturated ketones by the enoate reductase enzymes of P. citrinum CBMAI 1186.
- Ferreira, Irlon M.,Meira, Eloá B.,Rosset, Isac G.,Porto, André L.M.
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- Asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives: Which possesses the highest activity to protect DNA or scavenge radical?
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A series of asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives were synthesized. Their antioxidant abilities in protecting DNA against 2,2′-azobis(2-amidinopropane hydrochloride)-induced oxidation and scavenging 2,2′-azinobis(3-ethylbenzothiazoline-6- sulfonate) cationic radical (ABTS) radical were evaluated. In synthesis, the Michael addition reactions between phenylhydrazine and asymmetrical ferrocenylidene curcumin derivatives exhibit evident regioselectivity. The direction of addition depends on whether the benzene ring is substituted or not. The antioxidant abilities of compounds will increase when the ferrocenyl group is introduced. Moreover, such improvement derived from ferrocenyl group is also related to other substituent groups in molecule, not independent. Interestingly, p-dimethylamino group which is never considered as an active group, however, exhibits the best activity in protecting DNA and scavenging ABTS radical.
- Li, Pei-Ze,Liu, Zai-Qun
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p. 3478 - 3490
(2014/06/24)
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- New spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cyclo addition reaction and their conformational structures
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Crossed-aldol condensation reaction of aromatic aldehydes with ketones such as; acetone and cyclohexanone leads to the efficient formation of cross conjugated α,β-unsaturated ketones in excellent yield. The intermolecular and then intramolecular Michael addition reaction of α,β-unsaturated ketones derived from acetone and cyclohexanone with (thio)barbituric acids lead to synthesis new type of 7,11-diaryl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone and 2,4-diaryl-1'H-spiro[bicyclo[3.3.l]nonane-3,5'-pyrimidine]-2',4',6',9(3'H)-tetraone, respectively in good yield. Structure elucidation is carried out by 1H NMR, 13C NMR, FT-IR, UV-Visible, mass spectroscopy and X-ray crystallography techniques. A possible mechanism of the formation is discussed. The structural conformation also demonstrated by coupling constants derived from dihedral angles between vicinal and geminal protons. The 1H NMR spectra of NH protons of spiro compounds derived from barbituric acid show a broad singlet peak instead, these protons in the spiro compounds derived from thiobarbituric acid show two distinct peaks.
- Pesyan, Nader Noroozi,Noori, Sirons,Poorhassan, Soodabeh,ahin, Ertan
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p. 423 - 440
(2015/02/02)
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- A sulfur ylides-mediated domino benzannulation strategy to construct biaryls, alkenylated and alkynylated benzene derivatives
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An efficient domino benzannulation strategy with the participation of sulfur ylides for the construction of biaryl compounds is disclosed. It could also be extended to the synthesis of alkenylated and alkynylated benzene derivatives under mild conditions. This versatile strategy combined with traditional metal-catalyzed cross-coupling methods should offer a practical route to construct complex multiaryl compounds.
- Gao, Fei,Huang, You
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supporting information
p. 2422 - 2428
(2014/09/17)
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- O-monoacyltartaric acid catalyzed enantioselective conjugate addition of a boronic acid to dienones: Application to the synthesis of optically active cyclopentenones
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Enantioselective conjugate addition of styrylboronic acid to dienones was effectively catalyzed by an O-monoacyltartaric acid to afford monostyrylated products with good enantioselectivity. The RCM of the monostyrylated products using the Hoveyda-Grubbs II catalyst afforded optically active cyclopentenones, including a synthetic intermediate of the antitumor agent TEI-9826. The study shows that a diene additive such as 1,6-heptadiene or diallyl ether was essential for the RCM.
- Sugiura, Masaharu,Kinoshita, Ryo,Nakajima, Makoto
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supporting information
p. 5172 - 5175
(2014/12/11)
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- Copper-catalyzed rearrangement of N-aryl nitrones into epoxyketimines
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Please pass the oxygen: A new method for the preparation of trans-α,β-epoxyketimines has been achieved through a copper-catalyzed rearrangement of (E)-α,β-unsaturated nitrones. The scope and tolerance of the method is evaluated and the synthetic utility of the products is demonstrated. The new transformation provides facile access to an unusual, densely functionalized intermediate that can be exploited for further synthetic application. Copyright
- Mo, Dong-Liang,Anderson, Laura L.
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supporting information
p. 6722 - 6725
(2013/07/26)
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- Enviornmentally benign michael and claisen schmidt reaction of aromatic carbonyl compounds by alkaline polyionic resin
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A regioselective Michael reaction between aryl methyl ketones and α,β-unsaturated compounds has been carried out using basic polyionic resin as a reusable reagent. Results indicate that the reaction proceeds in consecutive manner as double Michael (27-65%) and triple Michael (40-45%) products with overall yields of 55-80%. Moreover, A-2XMP resin has also been applied on Claisen Schmidt condensations of aromatic aldehydes and ketones (acyclic as well as cyclic) under different reaction conditions yielding dehydrated products in 82-94% yield. The reactions give an opportunity for easy separation, reusability of polyionic resin and easy purification of products in continuous or multiple processing of organic compounds.
- Jaitak, Vikas,Kaul,Das, Pralay
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p. 1137 - 1145
(2013/09/24)
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- Novel one-pot three-component coupling reaction with trimethylsilylmethyl- phosphonate, acyl fluoride, and aldehyde through the horner-wadsworth-emmons reaction
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A novel three-component coupling between trimethylsilylmethylphosphonate, acyl fluoride, and aldehyde has been developed. A sequential nucleophilic addition of lithio-trimethylsilylmethylphosphonate to the acyl fluoride and Horner-Wadsworth-Emmons reaction of an aldehyde with the lithio-β- ketophosphonate generated in situ by desilylation at the α-position of the α-silyl-β-ketophosphonate by fluoride took place cleanly in a one-pot operation. Various E- and Z-enones were obtained in high yields with high stereoselectivities by this one-pot procedure.
- Umezawa, Taiki,Seino, Tomoya,Matsuda, Fuyuhiko
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experimental part
p. 4206 - 4209
(2012/09/25)
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- Synthesis and Antimalarial Activity of Dihydroperoxides and Tetraoxanes Conjugated with Bis(benzyl)acetone Derivatives
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Dihydroperoxides and tetraoxanes derived from symmetrically substituted bis(arylmethyl)acetones were synthesized in modest to good yields using several methods. Three of these compounds exhibit an important in vitro antimalarial activity (1.0μm≤IC50≤5.0μm) against blood forms of the human malaria parasite Plasmodium falciparum.
- Franco, Lucas Lopardi,de Almeida, Mauro Vieira,e Silva, Luiz Francisco Rocha,Vieira, Pedro Paulo Ribeiro,Pohlit, Adrian Martin,Valle, Marcelo Siqueira
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experimental part
p. 790 - 797
(2012/06/18)
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- COMPOUNDS USEFUL AGAINST KINETOPLASTIDEAE PARASITES
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Dibenzylidene and heterobenzylideneacetone derivatives, related 4-piperidones, related 4-thiopyranones and the corresponding sulfinyl- and sulfonyl-analogues for their use for prophylaxis or treatment of trypanosomiasis and leishmaniasis.
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Page/Page column 16
(2012/09/05)
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- Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors
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Anti-melanogenesis screening of 47 synthesized curcumin-like diarylpentanoid analogues was performed to show that some had a potent inhibitory effect on the melanogenesis in B16 melanoma cells. Their actions were considered to be mostly due to tyrosinase inhibition, tyrosinase expression inhibition, and melanin pigment degradation. The structure-activity relationships of those curcumin-like diarylpentanoid analogues which inhibited the melanogenesis and tyrosinase activity were also discussed. Of those compounds assayed, (2E,6E)-2,6-bis(2,5- dimethoxybenzylidene)cyclohexanone showed the most potent anti-melanogenesis effect, the mechanism of which is considered to be the degradation of the melanin pigment in B16 melanoma cells, affecting neither the tyrosinase activity nor tyrosinase expression. The Japanese Society of Pharmacognosy and Springer 2011.
- Hosoya, Takahiro,Nakata, Asami,Yamasaki, Fumie,Abas, Faridah,Shaari, Khozirah,Lajis, Nordin Hj,Morita, Hiroshi
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experimental part
p. 166 - 176
(2012/05/20)
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- Features of the chromatography-mass spectrometric identification of condensation products of the carbonyl compounds
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By the example of the condensation products of acetone with the simplest aromatic carbonyl compounds it was shown that the joint interpretation of mass spectrometric and chromatographic data in conjunction with a priori assumptions about the nature of the chemical structure allows the detection of the components of reaction mixtures that were not previously characterized by standard mass spectra or by retention indices on standard stationary phases. A necessary condition for solving such problems is creating a hypothesis about the sample composition that is possible for the expected products of the known organic reactions.
- Zenkevich,Ukolov
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experimental part
p. 1818 - 1828
(2012/01/07)
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- Lewis acid mediated diastereoselective synthesis of fused fluorinated spiroketal as potential biologically active compounds
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A series of substituted dibenzalacetones prepared using standard procedures were condensed with 5-methyl, 5-phenyl, and 5-trifluoromethyl-1,3- cyclohexanediones respectively, in toluene containing BF3·OEt as the Lewis acid catalyst. The reaction was found to be highly diastereoselective (dr, 9:1). The resulting spiroketals 1a-r were formed in moderate to good yields. In addition, a synthetically and biologically useful by-product identified as chromenone 7 was observed.
- Agbaje, Oluropo C.,Fadeyi, Olugbeminiyi O.,Okoro, Cosmas O.
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scheme or table
p. 5297 - 5300
(2011/10/30)
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- Mosquito larvicidal studies of some chalcone analogues and their derived products: Structure-activity relationship analysis
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A series of chalcone analogues and some of their derivatives were synthesized and subjected to the mosquito larvicidal study. Chalcones having electron releasing group(s) on either ring A or ring B showed high toxicity. Electron withdrawing group(s), especially at ring B, reduced the activity of chalcones. The activity was abruptly decreased due to replacement of ring A by CH3, extension of conjugation or blocking of α,β- unsaturated ketone part of chalcones by derivatization. Quantitative structure-activity relationship (QSAR) studies of these compounds were performed using various spatial, electronic and physicochemical parameters. Genetic Function approximation with linear and spline options was used as the chemometric tool for developing the QSAR models.
- Begum, Naznin A.,Roy, Nayan,Laskar, Rajibul A.,Roy, Kunal
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experimental part
p. 184 - 191
(2012/02/16)
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- Synthesis and structure-affinity relationships of novel dibenzylideneacetone derivatives as probes for ?-Amyloid Plaques
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A new and extensive set of dibenzylideneacetone derivatives was synthesized and screened for affinity toward A1-42 aggregates. Structure-activity relationships revealed the binding of dibenzylideneacetones to be affected by various substituents. The introduction of a substituent group in the ortho position reduced or abolished the binding. However, the para position was highly tolerant of sterically demanding substitutions. Three radioiodinated ligands (6, 70, and 71) and two 18F fluoro-pegylated (FPEG) ligands (83 and 85) were prepared, all of which displayed high affinity for A1-42 aggregates (Ki ranging from 0.9 to 7.0 nM). In biodistribution experiments, they exhibited good initial penetration (1.59, 4.68, 4.56, 4.13, and 5.15% ID/g, respectively, at 2 min) of and fast clearance from the brain. Autoradiography with sections of postmortem AD brain and transgenic mouse brain confirmed the high affinity of these tracers. These preliminary results strongly suggest the dibenzylideneacetone structure to be a potential new scaffold for β-amyloid imaging probes.
- Cui, Mengchao,Ono, Masahiro,Kimura, Hiroyuki,Liu, Boli,Saji, Hideo
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experimental part
p. 2225 - 2240
(2011/06/17)
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- Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors
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A series of dibenzylideneacetones (A1-A12) and some of their pyrazolines (B1-B4) were synthesized and evaluated in vitro for blood stage antiplasmodial properties in Plasmodium falciparum culture using SYBR-green-I fluorescence assay. The compound (1E, 4E)-1,5-bis(3,4-dimethoxyphenyl)penta-1,4-dien-3-one (A9) was found to be the most active with IC50 of 1.97 μM against chloroquine-sensitive strain (3D7) and 1.69 μM against chloroquine-resistant field isolate (RKL9). The MTT based cytotoxicity assay on HeLa cell line has confirmed that A9 is selective in its action against malaria parasite (with a therapeutic index of 166). Our results revealed that these compounds exhibited promising antiplasmodial activities which can be further explored as potential leads for the development of cheaper, safe, effective and potent drugs against chloroquine-resistant malarial parasites.
- Aher, Rahul Balasaheb,Wanare, Gajanan,Kawathekar, Neha,Kumar, Ravi Ranjan,Kaushik, Naveen Kumar,Sahal, Dinkar,Chauhan, Virander Singh
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supporting information; experimental part
p. 3034 - 3036
(2011/06/24)
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- BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER
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It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.
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Page/Page column 12
(2010/06/22)
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- N-heterocyclic carbenes of indazole: Ring enlargement reactions by α-halo ketones and dehalogenations of vicinal dihalides
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On decarboxylation, 1,2-dimethylindazolium-3-carboxylate forms the N-heterocyclic carbene, 1,2-dimethylindazol-3-ylidene, which deprotonates α-halo ketones. The resulting indazolium salt and the corresponding enolate form 1:1 adducts which undergo a ring enlargement to cinnolines. Reaction with 2-bromo-2,3-dihydro-1H-inden-1-one gives a 4- hydroxyspiro[cinnoline-3,2′-inden]-1′-one by ring enlargement reaction (X-ray crystal structure analysis). Vicinal dibromides undergo debromination under these conditions to give alkenes, and substrates with 1,2-dibromoethene partial structure give acetylenes. As 3-bromoindazole is found as the second product of this reaction, an E1cb mechanism, initiated by Br+ abstraction by the N-heterocyclic carbene of indazole, is suggested. Georg Thieme Verlag Stuttgart.
- Schmidt, Andreas,Snovydovych, Bohdan,Gjikaj, Mimoza
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experimental part
p. 2798 - 2804
(2009/04/05)
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- A simple, modular synthesis of substituted pyridines
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A simple, modular method to prepare highly substituted pyridines is disclosed. The method employs a cascade reaction comprising (1) a novel N-iminative, Cu-catalyzed cross-coupling of alkenylboronic acids at the N-O bond of α,β-unsaturated ketoxime O-pentafluorobenzoates, (2) electrocyclization of the resulting 3-azatriene, and (3) air oxidation affording highly substituted pyridines in moderate to excellent isolated yields (43-91%). Starting materials are readily available, and functional group tolerance is very good. Copyright
- Liu, Songbai,Liebeskind, Lanny S.
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p. 6918 - 6919
(2008/09/21)
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- Siloxyallenes revisited. A useful functional intermediate for the synthesis of (Z)-β-branched Morita-Baylis-Hillman type adducts and (Z)-chalcones
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Siloxyallenes proved to be a useful functional intermediate in the preparation of (Z)-β-branched Morita-Baylis-Hillman type adducts by the reaction of aldehydes with silylacetylenes or siloxypropynes. Various (Z)-chalcones were stereoselectively synthesized from siloxypropynes via siloxyallenes.
- Yoshizawa, Kazuhiro,Shioiri, Takayuki
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p. 6259 - 6286
(2008/02/04)
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