- Biocatalytic green alternative to existing hazardous reaction media: Synthesis of chalcone and flavone derivatives via the Claisen-Schmidt reaction at room temperature
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Owing to the increasing amount of waste materials around the globe, the conversion of waste or secondary by-products to value-added products for various applications has gained significant interest. Herein, two novel agro-food waste products, Musa sp. 'Malbhog' peel ash (MMPA) and Musa Champa Hort. ex Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon-carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly characterized using different sophisticated analytical techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffractometry (XRD), Brunauer-Emmett-Teller analysis (BET), Raman spectroscopy, scanning electron microscopy energy dispersive X-ray spectroscopy (SEM-EDS), transition electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) along with element detection using atomic absorption spectroscopy and ion chromatographic methods. These two approaches are metal free, as well as being devoid of any extra additives, co-catalysts, harsh conditions, the use of column chromatography for purification and result in a higher yield of the product within a short space of time. The catalytic abilities of the promoter were also examined to synthesize important bioactive molecules such as butein and apigenin at room temperature. With gram scale synthesis of the chalcone derivatives, the used catalysts (MMPA and MCPA) were further reused for five cycles and did not demonstrate any loss in catalytic activity.
- Tamuli, Kashyap J.,Sahoo, Ranjan K.,Bordoloi, Manobjyoti
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supporting information
p. 20956 - 20965
(2020/12/31)
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- Aryl-4,5-dihydro-1H-pyrazole-1-carboxamide derivatives bearing a sulfonamide moiety show single-digit nanomolar-to-subnanomolar inhibition constants against the tumor-associated human carbonic anhydrases IX and XII
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A series of new 3-phenyl-5-aryl-N-(4-sulfamoylphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide derivatives was designed here, synthesized, and studied for carbonic anhydrase (CAs, EC 4.2.1.1) inhibitory activity against the human (h) isozymes I, II, and VII (cytosolic, off-target isoforms), and IX and XII (anticancer drug targets). Generally, CA I was not effectively inhibited, whereas effective inhibitors were identified against both CAs II (KIs in the range of 5.2-233 nM) and VII (KIs in the range of 2.3-350 nM). Nonetheless, CAs IX and XII were the most susceptible isoforms to this class of inhibitors. In particular, compounds bearing an unsubstituted phenyl ring at the pyrazoline 3 position showed 1.3-1.5 nM KIs against CA IX. In contrast, a subset of derivatives having a 4-halo-phenyl at the same position of the aromatic scaffold even reached subnanomolar KIs against CA XII (0.62-0.99 nM). Docking studies with CA IX and XII were used to shed light on the derivative binding mode driving the preferential inhibition of the tumor-associated CAs. The identified potent and selective CA IX/XII inhibitors are of interest as leads for the development of new anticancer strategies.
- Ceruso, Mariangela,Gratteri, Paola,Hargunani, Priya,Kazaks, Andris,Leitans, Janis,Nocentini, Alessio,Supuran, Claudiu T.,Tadge, Nikhil,Tars, Kaspars,Toraskar, Mrunmayee P.
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- Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
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A series of the chalcone derivatives of the five-membered monoheterocyclic compounds, (E)-1-aryl-3-heteroarylpropen-1-ones, were prepared by aldol condensation of the corresponding aldehydes of thiophene, pyrrole, and furan with m- and p-substituted acetophenones. Similar condensation of the acetyl compounds of the heterocycles with m- and p-substituted benzaldehydes gave another series of the chalcone derivatives, (E)-1-heteroaryl-3-arylpropen-1-ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β-C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β-C of the heterocyclic compounds were plotted against those of the benzene derivatives. The resulting slopes were found to be close to the values of the aromaticity indices.
- Jeong, Eun Jeong,Lee, In-Sook Han
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p. 668 - 673
(2019/07/12)
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- Ultrasound-mediated synthesis, biological evaluation, docking and in vivo acute oral toxicity study of novel indolin-2-one coupled pyrimidine derivatives
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The work reports ultrasound-mediated greener synthesis of 11 novel 3-(4-(4-chlorophenyl)-6-(substituted phenyl/heteryl)pyrimidin-2-ylimino)indolin-2-one (7a–7k) derivatives. The synthesized derivatives were evaluated for their in vitro anticancer activity against a panel of selected human cancer cell lines of breast (MCF-7), cervix (HeLa), prostate (PC-3) and lung (A-549). Among the tested compounds, 7b exhibited most promising in vitro anticancer activity against HeLa, PC-3 and A-549 with GI50 value 15.38, 19.67 and 4.37?μM, respectively. The compounds (7a–7k) were also screened for induction of apoptosis and morphological changes in cancer cells at their GI50 concentration. The treatment of HeLa, PC-3 and A549 cancer cells with 7b and treatment of MCF-7 cancer cells with 7h showed apoptosis and morphological changes such as cell shrinkage, cell wall deformation and reduced number of viable cells. The compound 7b has shown almost 5.00 times more selectivity for PC-3 cancer cell lines in comparison to the RWPE-1 normal prostate epithelial cells. Molecular docking study has been carried out, which replicates results of biological activity in cases of initial hits 7b, 7c and 7d, suggesting that these compounds have a potential to become lead molecules in the drug discovery process. In silico ADMET study was performed for predicting pharmacokinetic properties and toxicity profile of the synthesized compounds and expressed good oral drug-like behaviour. An in vivo acute oral toxicity study was performed using Swiss albino mice for the most active compounds 7b and 7c, and results indicate that the compounds are non-toxic in nature.
- Nikalje, Anna Pratima G.,Tiwari, Shailee V.,Sangshetti, Jaiprakash N.,Damale, Manoj D.
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p. 3031 - 3059
(2018/02/06)
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- Evaluation of sulphonamide derivatives acting as inhibitors of human carbonic anhydrase isoforms I, II and Mycobacterium tuberculosis β-class enzyme Rv3273
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A series of novel sulphonamide derivatives was obtained from sulphanilamide which was N4-alkylated with ethyl bromoacetate followed by reaction with hydrazine hydrate. The hydrazide obtained was further reacted with various aromatic aldehydes. The novel sulphonamides were characterised by infrared, mass spectrometry, 1H- and 13C-NMR and purity was determined by high-performance liquid chromatography (HPLC). Human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and II and Mycobacterium tuberculosis β-CA encoded by the gene Rv3273 (mtCA 3) inhibition activity was investigated with the synthesised compounds which showed promising inhibition. The KIs were in the range of 54.6 nM–1.8 μM against hCA I, in the range of 32.1 nM–5.5 μM against hCA II and of 127 nM–2.12 μM against mtCA 3.
- Wani, Tanvi V.,Bua, Silvia,Khude, Pravin S.,Chowdhary, Abdul H.,Supuran, Claudiu T.,Toraskar, Mrunmayee P.
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p. 962 - 971
(2018/05/29)
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- Temperature dependence of the Raman spectrum of 1-(4-chlorophenyl)-3-(2-thienyl)prop-2-en-1-one
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The heterocyclic chalcone containing thiophene ring 1-(4-chlorophenyl)-3-(2-thienyl)prop-2-en-1-one, C13H9ClOS was synthesized and investigated using experimental techniques such as nuclear magnetic resonance (1H and
- de Toledo,da Costa,Al-Maqtari,Jamalis,Pizani
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- Synthesis, biological evaluation and 3D-QSAR study of novel 4,5-dihydro-1H-pyrazole thiazole derivatives as BRAFV600E inhibitors
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Many reports implied that the BRAF serine/threonine kinase was mutated in various types of human tumors, which were related with cell growth, survival and differentiation. To provide new therapeutic opportunities, a series of novel 4,5-dihydro-1H-pyrazole
- Zhao, Meng-Yue,Yin, Yong,Yu, Xiao-Wei,Sangani, Chetan B.,Wang, Shu-Fu,Lu, Ai-Min,Yang, Li-Fang,Lv, Peng-Cheng,Jiang, Ming-Guo,Zhu, Hai-Liang
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- Tetra-n-butylammonium bromide: A simple but efficient organocatalyst for alcohol oxidation under mild conditions
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A simple but efficient organocatalytic system with 5 mol% tetra-n-butylammonium bromide (TBAB) as the catalyst has been identified for alcohol oxidation for the first time. This organocatalytic system is compatible with a broad range of benzylic/allylic alcohols with various catalytically reactive groups. Besides, it shows excellent selectivity for secondary benzylic alcohols over aliphatic alcohols, and good selectivity over the primary benzylic alcohol site in 4-(1-hydroxyethyl)benzyl alcohol. Thus, the features of simplicity, high efficiency, selectivity and mildness of reaction conditions associated with this TBAB organocatalytic system suggest its potential for widespread use in synthetic chemistry.
- Ma, Xinyi,Li, Zhongfeng,Liu, Feijie,Cao, Shengli,Rao, Honghua
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supporting information
p. 1741 - 1746
(2014/06/09)
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- Synthesis and anti-bacterial activity of some heterocyclic chalcone derivatives bearing thiofuran, furan, and quinoline moieties
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36 Novel heterocyclic chalcone derivatives were synthesized and tested for their anti-bacterial activity. Some compounds presented good anti-microbial activities against Gram-positive bacteria (including the multidrug-resistant clinical isolates). This cl
- Zheng, Chang-Ji,Jiang, Sheng-Ming,Chen, Zhen-Hua,Ye, Bai-Jun,Piao, Hu-Ri
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experimental part
p. 689 - 695
(2012/06/01)
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- Studies on the nuclear magnetic resonance spectra of (E)-1-Aryl-3-(2- and 3-thienyl)-2-propenones and unique observation of 4J and 5J coupling in their 1H-1H COSY
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1H and 13C NMR spectra of series of (E)-1-aryl-(2- and 3-thienyl)-2-propenones, that are aldol condensation products between 2- and 3-thiophenecarbaldehydes and m- and p-substituted acetophenones, were examined to make complete assig
- Han Lee, In-Sook,Jeon, Hyun Ju,Lee, Chang Kiu
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scheme or table
p. 687 - 692
(2011/12/03)
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- Screening of biological activities of a series of chalcone derivatives against human pathogenic microorganisms
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In an effort to develop new antimicrobial agents, a series of chalcone derivatives, 3-60, were prepared by Claisen-Schmidt condensation of appropriate acetophenones and 2-furyl methyl ketones with appropriate aromatic aldehydes, furfural, and thiophene-2-carbaldehyde in an aqueous solution of NaOH and EtOH at room temperature. The synthesized compounds were characterized by means of their IR- and NMR-spectral data, and elemental analysis. All compounds were tested for their antibacterial and antifungal activities by the disc diffusion method. For the most active compounds, also minimum inhibitory concentrations (MICs) were determined.
- Karaman, Isa,Gezegen, Hayreddin,Guerdere, M. Burcu,Dingil, Alparslan,Ceylan, Mustafa
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experimental part
p. 400 - 408
(2010/09/04)
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- Substituent chemical shifts of (E)-1-aryl-3-thienylpropen-1-ones
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Substituent chemical shifts were examined for the 2- and 3-thiophene derivatives of chalcone and compared to the thiophene series of derivatives with the phenyl series. The chemical shift values for the α-carbons of the enones showed and inverse correlation with the Hammett σ values, but the correlation coefficients were moderate (r = 0.836 - 0.878). On the other hand, the β-carbons showed a normal correlation with excellent correlation coefficients (r = 0.994). The absolute magnitude of the p values for the α-carbon are about half of those of the β-carbon. The observation may be the result of a through-space transition of the electronic effect of the substituents in addition to the through bond transition.
- Lee, In-Sook Han,Jeon, Hyun Ju,Yu, Ji Sook,Lee, Chang Kiu
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experimental part
p. 1689 - 1694
(2010/10/21)
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- Two variations of solvent-reduced wittig olefination reactions - Comparison of solventless wittig reactions to wittig reactions under ultrasonication with minimal work-up
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Stabilized and semi-stabilized phosphoranes can be subjected to solventless Wittig reactions with carbaldehydes. Simple heating of a mixture of added components at 100°C in an electric oven gives the corresponding olefins in good yield. Alternatively, the Wittig reactions can be carried out in a biphasic medium under ultrasonication. In this case, the Wittig products can be isolated by simple evaporation of the organic phase without additional work-up.
- Watanabe, Masataka,Morais, Goreti Ribeiro,Mataka, Shuntaro,Ideta, Keiko,Thiemann, Thies
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p. 909 - 915
(2007/10/03)
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- The pyrrole moiety as a template for COX-1/COX-2 inhibitors
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Aroyl- and thiophene-substituted pyrrole derivatives have been synthesized as a new class of COX-1/COX-2 inhibitors. The inhibition of COX-1 was evaluated in a biological system using bovine PMNLs as the enzyme source, whereas LPS-stimulated human monocytes served as the enzyme source for inducible COX-2. The determination of the concentration of arachidonic acid metabolites was performed by HPLC for COX-1 and RIA for COX-2. Variation of the substitution pattern led to a series of active compounds which showed inhibition for COX-1 and COX-2. Structural requirements for the development of COX-1/COX-2 inhibitors are discussed. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
- Dannhardt, Gerd,Kiefer, Werner,Kraemer, Godehard,Maehrlein, Sabine,Nowe, Ulrike,Fiebich, Bernd
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p. 499 - 510
(2007/10/03)
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- Solution phase synthesis of a spiro[pyrrolidine-2,3'-oxindole] library via a three component 1,3-dipolar cycloaddition reaction
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A combinatorial library of 26,500 spiro[pyrrolidine,-2,3-oxindoles] was prepared in a single-compound format by a facile intermolecular 1,3-dipolar cycloaddition. An azomethine ylide, generated by the decarboxylative condensation of an isatin 1 with an α-amino acid 2, was trapped by a transchalcone 3 to afford heterocycles of the general structure 4. The regio- and stereochemistry of a representative product was determined by single crystal X-ray structure.
- Fokas, Demosthenes,Ryan, William J.,Casebier, David S.,Coffen, David L.
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p. 2235 - 2238
(2007/10/03)
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- Automated parallel synthesis of chalcone-based screening libraries
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Using a variety of condensation and cyclization reactions, nine combinatorial arrays of individual chalcone derivatives, over 74,000 in all, were produced in 50 μM quantities. The ease with which a broad range of diversity can be fabricated around a single molecular motif using automated parallel solution phase synthesis has been demonstrated.
- Powers, David G.,Casebier, David S.,Fokas, Demosthenes,Ryan, William J.,Troth, Jonah R.,Coffen, David L.
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p. 4085 - 4096
(2007/10/03)
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- Studies of Substituent Effects by Carbon-13 NMR Spectroscopy. Thiophene and Furan Chalcone Analogues
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13C NMR spectra of 39 thiophene and furan chalcone analogues in CDCl3 solutions are reported.The effect of substituents on the 13C chemical shifts in the phenyl and in the 5-membered rings is discussed. 13C NMR shifts are correlated with Hammett parameter
- Musumarra, Giuseppe,Ballistreri, Francesco P.
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p. 384 - 391
(2007/10/02)
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