- Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
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A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields.
- Tanemura, Kiyoshi,Rohand, Taoufik
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supporting information
(2021/02/27)
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- Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC
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A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.
- Bolm, Carsten,Molitor, Claude,Rissanen, Kari,Schumacher, Christian,Smid, Sabrina,Truong, Khai-Nghi
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p. 14213 - 14222
(2021/09/07)
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- In silico studies, nitric oxide, and cholinesterases inhibition activities of pyrazole and pyrazoline analogs of diarylpentanoids
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A new series of pyrazole, phenylpyrazole, and pyrazoline analogs of diarylpentanoids (excluding compounds 3a, 4a, 5a, and 5b) was pan-assay interference compounds-filtered and synthesized via the reaction of diarylpentanoids with hydrazine monohydrate and phenylhydrazine. Each analog was evaluated for its anti-inflammatory ability via the suppression of nitric oxide (NO) on IFN-γ/LPS-activated RAW264.7 macrophage cells. The compounds were also investigated for their inhibitory capability toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), using a modification of Ellman's spectrophotometric method. The most potent NO inhibitor was found to be phenylpyrazole analog 4c, followed by 4e, when compared with curcumin. In contrast, pyrazole 3a and pyrazoline 5a were found to be the most selective and effective BChE inhibitors over AChE. The data collected from the single-crystal X-ray diffraction analysis of compound 5a were then applied in a docking simulation to determine the potential binding interactions that were responsible for the anti-BChE activity. The results obtained signify the potential of these pyrazole and pyrazoline scaffolds to be developed as therapeutic agents against inflammatory conditions and Alzheimer's disease.
- Mohd Faudzi, Siti Munirah,Leong, S. Wei,Auwal, Faruk A.,Abas, Faridah,Wai, Lam K.,Ahmad, Syahida,Tham, Chau L.,Shaari, Khozirah,Lajis, Nordin H.,Yamin, Bohari M.
-
-
- Curcumin-cinnamaldehyde hybrids as antiproliferative agents against women’s cancer cells
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Curcumin and cinnamaldehyde are natural products whose antineoplastic activity has been well explored in biological evaluations. However, their poor chemical stability under physiological conditions has been an obstacle to their use as therapeutic agents. Herein, we designed and synthesized two series of curcumin-cinnamaldehyde hybrids by removing reactive functionalities, including β-diketone and aldoxyl moieties. All compounds were evaluated by the MTT assay to determine their antiproliferative activity against women’s cancer cells. Compound 5a (3′-hydroxychalcone) demonstrated potent antiproliferative activity against all cancer cell lines tested, with IC50 values ranging from 2.7 to 36.5 μM. Compound 5a was more active and selective than curcumin and cinnamaldehyde (parent compounds) against the CaSki, SiHa, C33, and A431 cell lines, displaying a higher selectivity index (SI = 8.5) than curcumin (SI = 0.8) toward the non-tumorigenic HaCaT cell line. Clonogenic experiments indicated that compound 5a inhibited A431 colony formation in a concentration-dependent manner. In addition, 5a was more stable than its parent compounds in pH 7.4 at 37 °C. In silico investigations suggested that 5a has good drug-likeness properties. In conclusion, our results indicate the use of curcumin and cinnamaldehyde as parent compounds for the design of hybrids with attractive antiproliferative activity and chemical stability.
- Anselmo, Daiane B.,Polaquini, Carlos R.,Marques, Beatriz C.,Ayusso, Gabriela M.,Assis, Letícia R.,Torrezan, Guilherme S.,Rahal, Paula,Fachin, Ana L.,Calmon, Marília F.,Marins, Mozart A.,Regasini, Luis O.
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p. 2007 - 2015
(2021/08/31)
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- Anti-corrosive property of bioinspired environmental benign imidazole and isoxazoline heterocyclics: A cumulative studies of experimental and DFT methods
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In the present study, four imidazoline (IDZ) and four isoxazolines (ISO) heterocyclics differing in the nature of methoxy (-OCH3) and aromatic (phenyl and naphthyl) moieties are synthesized, characterized and evaluated as corrosion inhibitors for mild steel in acidic solution of 1 M HCl. Results showed that imidazoline based heterocyclic compounds are better corrosion inhibitors than isoxazoline based heterocyclics and both classes of compounds showed inhibition efficiency of more than 85% at 20 mgL?1 concentration. Results further showed that inhibitors containing methoxy, phenyl, and naphthyl moieties showed higher protection efficiency as compared to the inhibitors without these moieties. PDP Study revealed that investigated IDZs and ISOs acted as mixed type inhibitors and their adsorption on the metallic surface followed the Langmuir adsorption isotherm model. All the experimental results were corroborated by density function theory (DFT) based quantum chemical calculations. Numerous DFT based indices calculated for neutral as well as protonated forms of the IDZs and ISOs in order to get better insight about metal-IDZs/ISOs interactions. Outcomes of the DFT analysis showed that protonated (cationic) form of the all the inhibitors are more strongly adsorbed on the metallic surface as compared to their neutral form.
- Ramkumar, Sowmya,Nalini,Quraishi, Mumtaz A.,Ebenso, Eno E.,Verma, Chandrabhan
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supporting information
p. 103 - 119
(2019/12/24)
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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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- Efficient catalytic performance of calcined tungstophosphoric acid for the Claisen-Schmidt condensation under solvent-free reaction
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Effect of calcination of tungstophosphoric acid catalyst was evaluated in terms of the synthesis of chalcone derivatives via Claisen-Schmidt condensation using the reaction of acetophenone and several substituted aldehydes. The catalyst was characterized before and after calcination by FT-IR to assess the effectiveness of the synthesis of the desired products. The calcined tungstophosphoric acid catalyst (HPW-CL) showed a better performance and high yield of Claisen-Schmidt products in a short period of time. It was also found out that the calcined tungstophosphoric acid provides a chemo selective, efficient and environmentally benign synthesis of chalcone in an excellent yield in a solvent-free system.
- Alharthi, Abdulrahman I.
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p. 2579 - 2584
(2019/10/02)
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- Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes
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Formal [5 + 1] cycloadditions between aryl-substituted vinylcyclopropanes and nitrenoid precursors are reported. The method, which employs Rh2(esp)2 as a catalyst, leads to the highly regioselective formation of substituted tetrahydropyridines. Preliminary mechanistic studies support a stepwise, polar mechanism enabled by the previously observed Lewis acidity of Rh-nitrenoids. Overall, this work expands the application of nitrene-transfer cycloaddition, a relatively underexplored approach to heterocycle synthesis, to the formation of six-membered rings.
- Combee, Logan A.,Johnson, Shea L.,Laudenschlager, Julie E.,Hilinski, Michael K.
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supporting information
p. 2307 - 2311
(2019/04/10)
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- Design, synthesis and biological evaluation of novel dihydropyrimidine-2-thione derivatives as potent antimicrobial agents: Experimental and molecular docking approach
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Introduction: Dihydropyrimidine scaffold represent an important class of pharmacologically active nitrogen containing heterocyclic compounds. A wide range of molecules with dihydropyrimidine moieties have important role in medicinal chemistry on account of their potential biological activities. Methodology: A series of 3,4-dihydropyrimidine-2(1H)-thione derivatives have been designed and synthesized in a concise way through condensation of variously substituted chalcones with thiourea in alkaline alcoholic solutions. In order to investigate their biological significance, these compounds were tested for their in vitro antimicrobial potential against various bacterial and fungal strains. Moreover, the experimental results were supported by molecular docking studies. Results and Discussion: The newly synthesized compounds were characterized by the usual spectroscopic techniques In case of antibacterial activity, the compounds 5 (40.3±0.44 mm), 12 and 13 (almost 35 mm) exhibited highest zone of inhibitions against Methicillin-resistant Staphylococcus auerus (MRSA) bacterial strain as compared to the standard drug Cefixime. These compounds displayed moderate to good activities against all attempted fungal strains. In docking analysis, it has been observed that compounds 8 (-6.4017 Kcal/mol) and 10 (-6.1319 Kcal/mol) revealed significant binding affinity against penicillin binding protein (PDB ID: 1VQQ), while compounds 1 (-143.23 Kcal/mol) and 2 (-146.99 Kcal/mol) showed best activity for shikimate dehydrogenase (PDB ID: 3DON). Conclusion: In conclusion, we have designed, synthesized and characterized an interesting series of biologically active dihydropyrimidine derivatives. Remarkably, most of the synthesized compounds were found more active against all tested bacterial strains in comparison to the standard drug Cefixime as manifested by experimental as well as theoretical results.
- Mughal, Ehsan Ullah,Sadiq, Amina,Hamayun, Muhammad,Zafar, Muhammad Naveed,Fatima, Nighat,Yameen, Muhammad Arfat,Muhammad, Syed Aun,Mumtaz, Amara,Ahmed, Ishtiaq,Fatima, Tehseen
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p. 1189 - 1201
(2018/11/01)
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- High pressure-assisted low-loading asymmetric organocatalytic conjugate addition of nitroalkanes to chalcones
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The application of high pressure (up to 9 kbar) allows for relatively fast (1-5 h) and highly enantioselective 1,4-addition of nitromethane and 2-nitropropane to chalcones at room temperature with substantial reduction of catalyst loading (0.2-1 mol% of cinchona alkaloid-based thioureas and squaramides). Various γ-nitroketones were obtained at 9 kbar with high yield and enantioselectivity (up to 98%), whereas in control experiments at atmospheric pressure usually only a small amount (10%) of products were formed after 20 h.
- Cholewiak, Agnieszka,Adamczyk, Kamil,Kopyt, Micha?,Kasztelan, Adrian,Kwiatkowski, Piotr
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supporting information
p. 4365 - 4371
(2018/06/22)
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- A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water
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A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.
- Gao, Pei-Sen,Zhang, Kan,Yang, Ming-Ming,Xu, Shan,Sun, Hua-Ming,Zhang, Jin-Lei,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen
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supporting information
p. 5074 - 5077
(2018/05/26)
-
- Asymmetric 1,4-Conjugate Addition of Diarylphosphines to α,β,γ,δ-Unsaturated Ketones Catalyzed by Transition-Metal Pincer Complexes
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An enantioselective asymmetric 1,4-addition of diarylphosphines to linear α,β,γ,δ-unsaturated dienones was developed. A series of chiral PCP- and PCN-transition-metal (Pd, Pt and Ni) pincers, themselves prepared catalytically via asymmetric hydrophosphination, were sequentially screened to reveal the roles of backbone architecture and metal ion in catalyst design. The selected ester-functionalized PCP-palladium pincer afforded the chiral 1,4-phosphine adducts in excellent yields with up to >99% ee. The same catalyst when utilized for the hydrophosphination of an α,β,γ,δ-unsaturated malonate ester also revealed the critical role played by the ester functionality on the ligand backbone in dictating the enantioselectivity of the 1,6-adduct.
- Yang, Xiang-Yuan,Tay, Wee Shan,Li, Yongxin,Pullarkat, Sumod A.,Leung, Pak-Hing
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supporting information
p. 5196 - 5201
(2015/11/09)
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- Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxide inhibitors
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A series of forty-five 1,5-diphenylpenta-2,4-dien-1-one analogues were synthesized and evaluated for their nitric oxide (NO) inhibition activity in IFN-γ/LPS-activated RAW 264.7 cells. Compounds 3h, 7a, 7d and 7e exhibited comparable or significantly higher activity than the standard, curcumin (IC50 = 14.69 ± 0.24 μM). Compound 7d, a 5-methylthiophenyl-bearing analogue, displayed the most promising NO-inhibitory activity with an IC50 value of 10.24 ± 0.62 μM. The 2D and 3D QSAR analyses performed revealed that a para-hydroxyl group on ring B and an α,β-unsaturated ketone moiety on the linker are crucial for a remarkable anti-inflammatory activity. Based on ADMET and TOPKAT analyses, compounds 3h, 7a and 7d are predicted to be nonmutagenic and to exhibit high blood-brain barrier (BBB) penetration, which indicates that they are potentially effective drug candidates for treating central nervous system (CNS) related disorders.
- Mohd Faudzi,Leong,Abas,Mohd Aluwi,Rullah,Lam,Ahmad,Tham,Shaari,Lajis
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p. 1069 - 1080
(2015/06/25)
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- Synthesis, antimicrobial and cytotoxic activity of novel 1,5 benzodiazepine derivatives
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In the present study, a series of novel 2-(substituted phenyl)-3-styryl-2,3-dihydro- 1H-benzo [b] [1,4] diazepines (1-12) has been synthesized from 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones (1a-12a). 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones were prepared by condensing cinnamaldehyde with various aromatic ketones in the presence of 20% NaOH as base. Different 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones on cyclisation with o-phenylene diamine in the presence of NaOH as base resulted in 2-(substituted phenyl)-3-styryl-2,3-dihydro-1H-benzo [b] [1,4] diazepine derivatives. The structures of the newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR and mass spectroscopic studies. All titled compounds were screened for their antimicrobial and cytotoxic activities. Most of the compounds showed promising cytotoxic, antibacterial and antifungal activities.
- Bhat, K. Ishwar,Kumar, Abhishek,Prathyusha
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p. 161 - 164
(2019/01/16)
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- Synthesis and biological activity of 4-aryl-3-benzoyl-5- phenylspiro[pyrrolidine-2.3′-indolin]-2′-one derivatives as novel potent inhibitors of advanced glycation end product
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Diabetic complications and their detrimental effects caused by sugar derived substances, have been the serious issue for the last few years and have yet not been fully combated. The key point of the present study is to synthesize some newer chemical entities which can eradicate such ailments to the maximum possible extent. So with this aim synthesis of some biologically interesting spiro-indolone-pyrrolidine derivatives was accomplished by 1,3-dipolar cycloaddition reaction of azomethine ylide 6 generated in situ from isatin and benzyl amine with the substituted α,β-unsaturated carbonyl compounds 3 as dipolarophile, leading to the formation of new 4-aryl-3-benzoyl-5- phenylspiro[pyrrolidine-2.3′-indolin]-2′-one derivatives 7 stereoselectively in excellent yields. The synthesized compounds have been screened for their advanced glycation end (AGE) product formation inhibitory activity on the basis of their ability to inhibit the formation of AGEs in the bovine serum albumin (BSA)-glucose assay and have been found to exhibit significant activity against AGE formation.
- Kaur, Anjandeep,Singh, Baldev,Vyas, Bhawna,Silakari, Om
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p. 282 - 289
(2014/05/06)
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- Synthesis, characterization and biological activity studies of some substituted pyrimidine derivatives
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A new series of substituted 1-phenyl-3-styryl-4,5-dihydo-1H-pyrazoles (TP1-TP9) has been synthesized by the cyclisation of chalcones with phenyl hydrazine and glacial acetic acid and substituted 4-styryl-pyrimidin-2-ols (LP1-LP9) have been synthesized by the condensation of chalcones with urea in the presence of 40% NaOH as a base. The intermediate substituted 1,5-diphenylpenta-2,4-dien-1-ones were synthesized by condensing cinnamaldehyde with various substituted aromatic ketones in presence of 20% NaOH. The title compounds obtained were characterized by IR, 1H NMR, mass spectral data and were screened for antimicrobial, anticancer and antitubercular activity.
- Ishwar Bhat,Kumar, Abhishek,Thara,Kumar, Pankaj
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p. 271 - 276
(2019/01/21)
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- Aldol condensations of a variety of different aldehydes and ketones under ultrasonic irradiation using poly(N-vinylimidazole) as a new heterogeneous base catalyst under solvent-free conditions in a liquid-solid system
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An ultrasound-assisted aldol condensation reaction has been developed for a range of ketones with a variety of aromatic aldehydes using poly(N-vinylimidazole) as a solid base catalyst in a liquid-solid system. The catalyst can be recovered by simple filtration and reused at least 10 times without any significant reduction in its activity. The reaction is also amenable to the large scale, making the procedure potentially useful for industrial applications.
- Khaligh, Nader Ghaffari,Mihankhah, Taraneh
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p. 2167 - 2173
(2014/01/06)
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- NHC-catalyzed annulation of enals to 2,4-dien-1-ones: Efficient diastereoselective synthesis of 1,3-diaryl-4-styrenyl cyclopentenes
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Nucleophilic heterocyclic carbene (NHC)-catalyzed annulation strategy has been utilized for the efficient synthesis of styrenyl-substituted cyclopentenes from 2,4-dienones. Georg Thieme Verlag Stuttgart New York.
- Sinu,Padmaja,Jini,Lakshmi, K.C. Seetha,Nair
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supporting information
p. 1671 - 1674
(2013/09/02)
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- Two expedient 'one-pot' methods for synthesis of β-aryl-β- mercaptoketones over anhydrous potassium carbonate or amberlyst-15 catalyst
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Two expedient one-pot methods have been developed for synthesis of β-aryl-β-mercaptoketones using acetophenones, benzaldehydes and thiols as starting materials. The methods involve microwave irradiation (5min) of 1:1 mixtures of acetophenones and benzaldehydes over neutral alumina supported anhydrous potassium carbonate or amberlyst-15 in the first step, and that is followed by addition of thiol to the resulting material and keeping at room temperature for 1.5 h. Indian Academy of Sciences.
- Guha, Chayan,Mondal, Rina,Pal, Rammohan,Mallik, Asok K.
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p. 1463 - 1470
(2014/04/03)
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- Synthesis, structure, growth and characterization of an organic crystal: 1,5-diphenylpenta-2,4-dien-1-one
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1,5-Diphenylpenta-2,4-dien-1-one (DDO) chalcone single crystals, synthesized by a base-catalysed aldol condensation reaction between cinnamaldehyde and acetophenone, have been grown by the slow evaporation of an ethanol solution. The crystals belong to the orthorhombic system with centrosymmetric space group Pbca. The DDO crystals are transparent in the visible region and have a lower optical cut-off at ~445 nm with a band-gap energy of 2.87 eV. Thermogravimetry/differential scanning calorimetry thermal analysis shows that the crystal is stable up to 375 K and it has a good chemical stability. The vibrational patterns of the chalcone have been investigated by Fourier transform IR and Fourier transform Raman spectroscopy. Microhardness studies were also carried out to elucidate the mechanical behaviour. Theoretical calculations were performed using the Hartree-Fock method with 6-31G(d,p) as the basis set, and the first-order hyperpolarizability is 7.077 × 10 -30 electrostatic units, which is >25 times that of urea. The crystalline perfection evaluated by high-resolution X-ray diffraction analysis reveals multiple peaks. The molecular packing leads to a centrosymmetric arrangement, resulting in zero second harmonic generation [χ(2) = 0] efficiency. Interestingly, the bromo- and chloro-substituted chalcones are good nonlinear optical materials.
- Rajasekar,Muthu,Bhagavannarayana,Meenakshisundaram
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p. 914 - 920
(2012/10/29)
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- Lithium amidoborane, a highly chemoselective reagent for the reduction of α,β-unsaturated ketones to allylic alcohols
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Lithium amidoborane (LiNH2BH3, LiAB for short), is capable of chemoselectively reducing α,β-unsaturated ketones to the corresponding allylic alcohols at ambient temperature. A mechanistic study shows that the reduction is via a double hydrogen transfer process. The protic H(N) and hydridic H(B) in amidoborane add to the O and C sites of the carbonyl group, respectively.
- Xu, Weiliang,Zhou, Yonggui,Wang, Ruimin,Wu, Guotao,Chen, Ping
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supporting information; experimental part
p. 367 - 371
(2012/01/13)
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- Iodine-catalysed conjugate addition of indole with α- cinnamylideneketones: Formation of β-(3-indolyl)-α,β-dihydro- α-cinnamylideneketones and bis(3-indolyl)methylbenzene
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β-(3-Indolyl)-α,β-dihydro-α-cinnamylideneketones and bis(3-indolyl)methylbenzene have been obtained in moderate to good yield by conjugate addition of indole with α-cinnamylideneketones under mild reaction condition in dry ethanol using iodine as catalyst. The structures of the products have been established from their spectral data.
- Pal, Rammohan,Mandal, Tapas K.,Mallik, Asok K.
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experimental part
p. 619 - 623
(2011/06/21)
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- Amberlyst-15 catalysed microwave assisted cross-aldol condensation between ketones and aldehydes under solvent free condition
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Amberlyst-15 has been applied as an efficient heterogeneous catalyst for the first time for rapid synthesis of α,α′-bis(arylmethylene) cycloalkanones, α,α′-bis(cinnamylidene)cycloalkanones, ′-cinnamylideneacetophenones and chalcones in very good yield by the reaction between various aldehydes and ketones under microwave irradiation. The new process for the cross-aldol condensation reaction works well in absence of any solvent. The yields are high and the process is environmentally benign.
- Pal, Rammohan,Mandal, Tapas K.,Guha, Chayan,Mallik, Asok K.
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experimental part
p. 711 - 717
(2012/03/11)
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- Design, synthesis, and bioactivities screening of a diaryl ketone-inspired pesticide molecular library as derived from natural products
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Three natural products, 1,5-diphenylpentan-1-one, 1,5-diphenylpent-2-en-1-one, and 3-hydroxy-1,5-diphenylpentan-1-one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as 'pharmacophores', a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)-1-(2,4-dichlorophenyl)-3-(furan-2-yl)- -prop-2-en-1-one (III2) was 1.20mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.
- Zhang, Hong,Jin, Hong,Ji, Lan-Zhu,Tao, Ke,Liu, Wei,Zhao, Hao-Yu,Hou, Tai-Ping
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experimental part
p. 94 - 100
(2012/06/01)
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- Asymmetric direct michael addition of acetophenone to α,β- unsaturated aldehydes
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The asymmetric direct Michael addition of ,-unsaturated aldehydes with acetophenone catalyzed by a Jorgensen-Hayashi-catalyst in methanol was developed and the corresponding Michael products of -keto aldehydes could be afforded in up to 82% yield and 98% ee. Georg Thieme Verlag Stuttgart.
- Li, Wenjun,Wu, Wenbin,Yang, Juanjuan,Liang, Xinmiao,Ye, Jinxing
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experimental part
p. 1085 - 1091
(2011/05/14)
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- 1,5-bis (2-hydroxyphenyl)pent-1,4-diene-3-one: A lead compound for the development of broad-spectrum antibacterial agents
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A systematic and comparative study has been made starting from a naturally-occurring chalcone nucleus to design effective antibacterial agents. The present investigation established 1,5-bis(2-hydroxyphenyl)pent-1,4-diene-3- one (1c) as a lead compound with potential against a panel of pathogenic bacterial strains. Staphylococcus (coagulase negative), Escherichia coli, Pseudomonas aeruginosa, Acenetobacter sp. and Klebsiella pneumoniae. Gentamycine and tetracycline were used as reference drugs. The mode of antibacterial action of Ic was also studied by scanning electron microscopy, which showed membrane disruption and cell lysis of the organisms during the exposure of the tested compound. In vitro toxicity tests demonstrated that all the bioactive compounds showed far less toxicity against human erythrocytes.
- Rani,Jain, Sapna,Kumar, Rita,Kumar, Anil
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experimental part
p. 31 - 35
(2011/07/31)
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- Synthesis and biological activity of some 3, 5-diarylisoxazoline derivatives: Reaction of substituted chalcones with hydroxylamine hydrochloride
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A series of 3-aryl-5-styrylisoxazoline/ 3,5-diarylisoxazoline derivatives were synthesized by the reaction of appropriately substituted chalcones and hydroxylamine hydrochloride in presence of alkali in ethanol. The synthesized heterocycles have been characterized on the basis of their chemical properties and spectroscopic data. These compounds were tested for biological activity against a variety of test organisms.
- Sharma, Vandana,Sharma
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experimental part
p. 203 - 209
(2011/01/03)
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- Preparation of plant-based insecticide chamaejasmin soluble liquid and its biological activity against Aphis craccivora and Pieris rapae
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Chamaejasmin is the mixture of many natural insecticidal ingredients from the ethanol extract of Stellera chamaejasme root. 1,5-Diphenyl-1-pentanone is one of the major insecticidal components. Chamaejasmin soluble liquid was prepared and its insecticidal activity against Aphis craccivora and Pieris rapae and its stability were evaluated. Results showed that it had good insecticidal activity and good stability. Its median lethal concentration (LC50) values (24 h after treatment) against Aphis craccivora and Pieris rapae were 26.9 and 38.6 mg L-1, respectively. The results of analysis of variance (ANOVA) indicated that after the prepared soluble liquid was stored at 54 ± 2 °C for 14 d or at room temperature for 12 months, its insecticidal activity had no significant change. The content of 1,5-diphenyl-1-pentanone in the soluble liquid was 0.39%.
- Tang, Xiaorong,Chen, Shaoling,Hou, Taiping
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experimental part
p. 6000 - 6006
(2010/12/25)
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- Ultrasound-promoted synthesis of 1,5-diarylpenta-2,4-dien-1-ones catalyzed by activated barium hydroxide
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1,5-Diarylpenta-2,4-dien-1-ones were synthesized with ultrasound irradiation in the presence of activated barium hydroxide as catalyst. Compared to conventional methods, the present methodology offers several advantages such as excellent yields, simple procedure, short reaction times, and milder conditions.
- Xin, Ying,Zang, Zhi-He,Chen, Feng-Lei
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experimental part
p. 4062 - 4068
(2009/12/24)
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- Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted
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A large series of chalcones were synthesized and studied against Staphylococcus aureus and Escherichia coli. Chalcones were either unsubstituted in ring A or possessed 4′-chloro or 3′,4′,5′-trimethoxy groups. Their other ring B was variously substituted. It was found that the anti-staphylococcal activity of chalcones was related to the energy difference between the two highest occupied molecular orbitals (HOMO and HOMO-1). Presence of hydroxyl group in ring B was not a determinant factor for the anti-staphylococcal activity, but the lipophilicity of ring A of the hydroxyl chalcones was of importance.
- Batovska, Daniela,Parushev, Stoyan,Stamboliyska, Bistra,Tsvetkova, Iva,Ninova, Mariana,Najdenski, Hristo
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experimental part
p. 2211 - 2218
(2009/09/30)
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- Enantioselective Michael addition of malononitrile to chalcones catalyzed by a simple quinine-Al(OiPr)3 complex: A simple method for the synthesis of a chiral 4H-pyran derivative
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Enantioselective Michael addition of malononitrile to chalcones was catalyzed by a simple quinine and Al(OiPr)3 complex and products were obtained in good ee as well as high yields, which facilitated the asymmetric synthesis of a biologically active 4H-pyran compound. The Royal Society of Chemistry 2009.
- Shi, Jian,Wang, Min,He, Ling,Zheng, Ke,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
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supporting information; experimental part
p. 4711 - 4713
(2010/01/16)
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- Aldol reactions of α-bromoalkyl phenyl ketones and aldehydes with tin(IV) iodide and tetrabutylammonium iodide
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Aldol reactions of α-bromoacetophenone and aldehydes in dichloromethane produced the corresponding E-α,β-unsaturated ketones at 25 °C with one equimolar amount of tin(IV) iodide, one equimolar amount of tetrabutylammonium iodide and one equimolar amount of N,N- diisopropylethylamine, and produced the corresponding β-hydroxy ketones at -80 °C with one equimolar amount of tin(IV) iodide and two equimolar amounts of tetrabutylammonium iodide. Using one equimolar amount of tin(IV) iodide and two equimolar amounts of tetrabutylammonium iodide at -80 °C in dichloromethane, α-bromopropiophenone reacted with aldehydes to afford the corresponding syn-α-methyl-β-hydroxy ketones selectively. Georg Thieme Verlag Stuttgart.
- Masuyama, Yoshiro,Ohtsuka, Masaru,Kondo, Ayako
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p. 3346 - 3348
(2008/09/18)
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- A new protocol for synthesis of α,β-unsaturated ketones using zirconium tetrachloride under microwave irradiation
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A facile one-pot synthesis of α,β-unsaturated carbonyl compound has been accomplished from ZrCl4 mediated condensation of α-bromo ketones with aryl aldehydes under microwave irradiation.
- Bora, Utpal,Saikia, Anil,Boruah, Romesh C.
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p. 2523 - 2526
(2007/10/03)
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- Aldol condensations of aldehydes and ketones catalyzed by rare earth(III) perfluorooctane sulfonates in fluorous solvents
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Rare earth(III) perfluorooctane sulfonates (RE(OPf)3) catalyze the efficient aldol condensation of different ketones with various aromatic aldehydes in fluorous solvents without the occurrence of any self-condensations. By simple separation of the fluorous phase containing only catalyst, reaction can be repeated several times.
- Yi, Wen-Bin,Cai, Chun
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p. 1553 - 1558
(2007/10/03)
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- A new lewis acid system palladium/TMSCl for Catalytic aldol condensation of aldehydes with ketones
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Palladium on charcoal effectively catalyzed the aldol condensation reactions of different ketones with aldehydes in the presence of trimethylsilyl chloride (TMSCl). The following reactions were investigated: (1) aromatic aldehydes with cycloalkanones, (2) aromatic aldehydes with aromatic ketones, (3) cycloalkanones with aliphatic aldehydes, and (4) the self-condensation reactions of aliphatic aldehydes and cycloalkanones.
- Zhu, Yulin,Pan, Yuanjiang
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p. 668 - 669
(2007/10/03)
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- KF-Al2O3 induced the condensation of 2-nitrofluorene and para-substituted acetophenones with aromatic aldehydes
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In the presence of KF-Al2O3 as a solid base, 2-nitrofluorene 1 condensed with aromatic aldehydes 2a-f in methanol to give 2-nitrodibenzofulvenes 3a-f in high yield. The para-substituted acetophenones 4a-f reacted with cinnamic aldehyde to give 1, 5-diaryl-2, 4-pentadien-1-ones 6a-f in moderate yield.
- Yan,Sun
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p. 3809 - 3814
(2007/10/03)
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- Carbon-carbon double bond formation between α-haloketones and aldehydes mediated by SnCl2/Na2SO3: Synthesis of (E) - α,β-unsaturated ketones
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One-pot reactions of α-haloketones with aldehydes in the presence of excess SnCl2/Na2SO3 or SnCl2 alone in THF at reflux were found to afford (E) - α,β-unsaturated ketones in fair to good yields.
- Lin,Yu,Zhang
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p. 271 - 276
(2007/10/02)
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- Indium-Induced Reaction of Phenacyl Iodide. Deiodinative Dimerization to β,γ-Epoxy Ketone and Aldol Condensation with Aldehydes
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The reaction of phenacyl iodide with indium metal gave 3,4-epoxy-1,3-diphenyl-1-butanone which, on treatment with silica gel, gave 2,4-diphenylfuran and 2,4-diphenyl-4-oxobutanal.Metallic indium as well as indium(I) iodide were found to mediate the aldol condensation between α-halo ketone and aldehyde.
- Araki, Shuki,Butsugan, Yasuo
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p. 727 - 729
(2007/10/02)
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- Reaction of α-Halogeno Ketones with Carbonyl Compounds Promoted by CeI3, CeCl3-NaI,or CeCl3-SnCl2
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Reaction of α-halogeno ketones with aldehydes in the presence of CeI3 in tetrahydrofuran is found to give α,β-unsaturated ketones in excellent yields under mild conditions.In contrast, treatment of α-halogeno ketones and carbonyl compounds with CeCl3-NaI or CeCl3-SnCl2 affords β-hydroxy ketones in good yields.It is assumed that these reactions proceed via cerium enolates.The combined reagents, however, cannot be applied to a Reformatsky-type reaction.Regiospecific and aldehyde chemoselective aldol synthesis are also described.
- Fukuzawa, Shin-ichi,Tsuruta, Takuya,Fujinami, Tatsuo,Sakai, Shizuyoshi
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p. 1473 - 1478
(2007/10/02)
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- Carbon-Carbon Bond Formation between α-Halogenoketones and Aldehydes Promoted by Cerium(III) Iodide or Cerium(III) Chloride-Sodium Iodide
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α-Halogenoketones react with aldehydes to form α,β-unsaturated ketones accompanied by dehalogenation in the presence of cerium(III) iodide, but the use of cerium(III) chloride-sodium iodide results in the formation of β-keto alcohols.
- Fukuzawa, Shin-ichi,Fujinami, Tatsuo,Sakai, Shizuyoshi
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p. 777 - 778
(2007/10/02)
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- The Reaction of Butadienylphosphonates with a Oxosulfonium Ylide, Phosphonium Ylides, and Ketone Enolates
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The condensation of diethyl (ethoxycarbonylmethyl)phosphonate (1a) with cinnamaldehyde in the presence of piperidine gave a 1:1 mixture of diethyl (1E,3E)- (2a) and (1Z,3E)-(1-ethoxycarbonyl-4-phenyl-1,3-butadienyl)phosphonates (2b) in 82percent yield, while a similar reaction using diethyl phosphonates (1c) exclusively gave diethyl (1E,3E)-phosphonates (4) in 78percent and 93percent yields, respectively.The reaction of the butadienylphosphonates 2-4 with dimethyloxosulfonium methylide (5) gave mixtures of (E)- and (Z)-(1-substituted 2-styrylcyclopropyl)phosphonates 7-9 in good yields.Similar treatment of the butadienylphosphonate 2 with phosphonium ylides 16a-c led to (3-substituted 1-ethoxycarbonyl-2-styrylcyclopropyl)phosphonates 17a-c in moderate yields.Reduction and oxidation of 7 were studied.The reaction of the phosphonates, 2 and 4, with ketone enolates and ketones resulted in the formation of unexpected olefins 22-24 and dienes 20a, b.The reaction mechanism is discussed.
- Minami, Toru,Yamanouchi, Takenobu,Tokumasu, Shigehumi,Hirao, Ichiro
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p. 2127 - 2131
(2007/10/02)
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- ALDOL CONDENSATIONS CATALYZED BY Co(II) COMPLEXES OF PYRIDINE-CONTAINING COPOLYMERS.
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The cross aldol condensations of aldehydes and ketones catalyzed by Co(II) complexes of pyridine-containing copolymers proceed under neutral conditions in DMF or DMSO to afford alpha , beta -unsaturated ketones without any by-product. The solid complex catalysts are capable of repeated use. The reactions of aromatic aldehydes and ketones give good results but not those of aliphatic compounds. Effects of substituent groups in chalcone formation are observed. The catalytic reaction features with the polymer-complex catalysts are compared with that with Co(II)-pyridine complex. The polymer-complex-catalyzed aldol condensations are discussed briefly in relation to the enzymatic reaction of Class II aldolase (metalloenzyme).
- Watanabe,Imazawa
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p. 3208 - 3211
(2007/10/02)
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- CATALYSE HETEROGENE PAR DES SELS ET SANS SOLVANT. III. SYNTHESE DE COMPOSES CARBONYLES α,β INSATURES A PARTIR D'ETHERS D'ENOLS SILYLES
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The reactions of silyl enol ethers with carbonyl compounds are activated by heterogeneous catalysis.Caesium fluoride is the best catalyst.Unsaturated ketones are directly obtained by condensation reactions of silyl enol ethers with aldehydes and ketones. 1,4 Addition with α,β-unsaturated carbonyl compounds gives 1,5 dicarbonyl products.This method is very convenient and the compounds obtained can easily be separated.We assume that the role of the salt in these reactions is to activate the silicon atom by anionic coordination to form a pentacoordinated silicon intermediate.
- Boyer, J.,Corriu, R. J. P.,Perz, R.,Reye, C.
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p. 157 - 166
(2007/10/02)
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