- Lewis acid catalyst system for Claisen-Schmidt reaction under solvent free condition
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Ca(OTf)2 in combination with NBu4.BF4 was established to function as an efficient catalyst system for one-pot Claisen-Schmidt condensation under neat conditions. Substituted acetophenones and benzaldehydes were coupled in situ to afford their corresponding chalcones in excellent yields. The method, with a broad range of substrate tolerance and mild operational conditions can produce assorted chalcone derivatives in moderate to high yields from easily accessible starting materials.
- Halpani, Chandni G.,Mishra, Satyendra
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- Targeting microbial resistance: Synthesis, antibacterial evaluation, DNA binding and modeling study of new chalcone-based dithiocarbamate derivatives
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New dithiocarbamate chalcone-based derivatives were synthesized, their structures were elucidated using different spectroscopic techniques. They were subjected to antimicrobial screening against selected Gram negative bacteria focusing on microbial resistance. Bacterial resistance was targeted via phosphoethanolamine transferase enzyme. Most of the synthesized compounds showed equal or higher activity to colistin standard. Compound 24 proved to be the most active candidate with MIC of 8 μg/ml against both Ps12 and K4 and MBC of 32 μg/ml against Ps12 and 16 μg/ml against K4 Molecular docking study showed that 20, 22, 24 and 25 had good binding affinity with active site residues via Thr280. DNA macromolecule was further targeted. Compounds 28 and 34 were recorded to have better DNA binding than doxurubucin with IC50 of 27.48 and 30.97 μg/ml respectively, suggesting that it could have a role in their higher antibacterial effect. Their docking into DNA has shown a clear intercalation matching with antibacterial data. Pharmacokinetics parameters of active compounds showed that they have better absorption through GIT.
- Ayman, Marwa,El-Messery, Shahenda M.,Habib, Elsayed E.,Al-Rashood, Sara T.,Almehizia, Abdulrahman A.,Alkahtani, Hamad M.,Hassan, Ghada S.
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p. 282 - 292
(2019/01/15)
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- Synthesis and biological evaluation of pyrimidine bridged combretastatin derivatives as potential anticancer agents and mechanistic studies
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A number of pyrimidine bridged combretastatin derivatives were designed, synthesized and evaluated for anticancer activities against breast cancer (MCF-7) and lung cancer (A549) cell lines using MTT assays. Most of the synthesized compounds displayed good
- Kumar, Bhupinder,Sharma, Praveen,Gupta, Vivek Prakash,Khullar, Madhu,Singh, Sandeep,Dogra, Nilambra,Kumar, Vinod
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p. 130 - 140
(2018/03/23)
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- An eco-friendly synthesis of 2-pyrazoline derivatives catalysed by CeCl 3· 7 H 2O
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Abstract: 1,3,5-triaryl-2-pyrazoline derivatives were synthesised by a condensation reaction between chalcones and phenyl hydrazine using cerium chloride heptahydrate as a catalyst. All these reactions were carried out in ethyl lactate (70%) as a green solvent. Easy and efficient work up, recyclability of solvent and catalyst are the key merits of this protocol. Graphical Abstract:: SYNOPSIS A facile protocol for the synthesis of 1,3,5-triaryl-2-pyrazolines is described. The solvent ethyl lactate, obtained from renewable sources, is biodegradable. The catalyst CeCl 3· 7 H 2O is a water-tolerant Lewis acid with low toxicity. Easy and clean work up, recyclable solvent and catalyst are merits of the protocol. The reaction works well for all systems giving good yields of the desired products.[Figure not available: see fulltext.].
- Bhat, Prabhat,Shridhar, Gomathi,Ladage, Savita,Ravishankar, Lakshmy
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p. 1441 - 1448
(2017/09/25)
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- Practical synthesis of β-isothiocyanato ketones from chalcones
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Practical synthesis of 1,3-diaryl-substituted 3-isothiocyanatopropan-1-ones based on the reaction of chalcones with thiocyanic acid generated in situ by treatment of thiocyanate ammonium with dilute sulfuric acid has been developed.
- Fesenko, Anastasia A.,Solovyev, Pavel A.,Shutalev, Anatoly D.
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p. 678 - 684
(2016/06/08)
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- Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach
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Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.
- Ventura, Thatiana Lopes Biá,Calixto, Sanderson Dias,De Azevedo Abrahim-Vieira, Bárbara,De Souza, Alessandra Mendon?a Teles,Mello, Marcos Vinícius Palmeira,Rodrigues, Carlos Rangel,De Mariz E Miranda, Leandro Soter,De Souza, Rodrigo Octavio Mendon?a Alves,Leal, Ivana Correa Ramos,Lasunskaia, Elena B.,Muzitano, Michelle Fraz?o
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p. 8072 - 8093
(2015/05/20)
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- Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives
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Novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives were synthesized and characterized by using spectral techniques like IR, 1H NMR, 13C NMR, COSY, DEPT, and GC-MS. All these compounds were screened for anti-fungal, anti-bacterial and anti-oxidant activity. Cyclohexenone derivatives, in general, showed better anti-fungal and anti-bacterial activity than parent chalcones. Whereas, all the Indazole derivatives showed very good anti-oxidant activity and some were also found to be active as anti-bacterial agent. Among the screened compounds, 15 was found to be most active as anti-fungal agent (against Rhizoctonia solani, LC 50 = 2.36 μg mL-1), 15b was found to be most active anti-bacterial agent (against Klebsiella pneumonia, MIC = 24.68 μg mL -1) and 14b emerged as most active anti-oxidant (IC50 = 19.81 μg mL-1).
- Shakil,Singh, Manish K.,Sathiyendiran,Kumar,Padaria, Jasdeep C.
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p. 120 - 131
(2013/03/14)
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- A novel series of 3,4-disubstituted dihydropyrazoles: Synthesis and evaluation for MAO enzyme inhibition
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In this study, the authors have designed and synthesized a novel series of 3-acyl-4-aryl-4,5-dihydropyrazoles, with the aim to obtain new potential scaffolds for the inhibition of both isoforms of monoamine oxidase.
- Cardia, Maria Cristina,Sanna, Maria Luisa,Meleddu, Rita,Distinto, Simona,Yanez, Matilde,Vina, Dolores,Lamela, Manuel,Maccioni, Elias
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- Synthesis and monoamine oxidase inhibitory activities of 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-1H-pyrazole derivatives
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Ten new 1-thiocarbamoyl-3-(phenyl and/or 4-substituted phenyl)-5-(3,4- dimethoxyphenyl and/or 2-chloro-3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazole derivatives were synthesized by reacting 1,3-diphenylpropen-1-ones and thiosemicarbazide. The chemical stru
- Palaska, Erhan,Aydin, Firat,Ucar, Guelberk,Erol, Dilek
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experimental part
p. 209 - 215
(2009/04/04)
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- Synthesis and antimicrobial activity of 1-(4-chlorophenyl)-3-(4-methoxy/3,4-dimethoxyphenyl)propan-1,3-diones and their 2-analogs
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The condensation of substituted acetophenones 1-5 with 4-methoxy- or 3,4-dimethoxy-benzaldehyde (6,7) in ethanolic NaOH gives the corresponding substituted 2-propen-1-ones (8-17) which on bromination yields substituted propan-1-ones (18-27).Refluxing of 1
- Singh, Rajvir,Malik, Om Parkash
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p. 455 - 459
(2007/10/02)
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