Synthesis, anti-tubercular activity and 3D-QSAR study of coumarin-4-acetic acid benzylidene hydrazides

Manvar, Atul; Malde, Alpeshkumar K.; Verma, Jaya; Virsodia, Vijay; Mishra, Arun Kumar; Upadhyay, Kuldip; Acharya, Hrishikesh D.; Coutinho, Evans C.; Shah, Anamik

doi:10.1016/j.ejmech.2008.01.016

Cited by 78 publications

(48 citation statements)

References 18 publications

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“…Coumarins, an important class of natural compounds have been studied extensively due to their vast medicinal significance [11, 12]. They have been reported for their analgesic [13], antibacterial [14], anticancer [15], anticoagulant [16], anti-inflammatory [13], anthelmintic [17], antifungal [14], antihepatitis C [18], antimutagenic [19], and antituberculosis [20] activities. Coumarins have also proved as potent nonpeptidic protease inhibitors [21], heat shock protein inhibitors [22], monoamine oxidase inhibitors [23], 17 β -hydroxysteroid dehydrogenase (17 β -HSD) type 1inhibitors [24], and TNF- α (tumor necrosis factor-alpha) inhibitors [25].…”

Section: Introductionmentioning

confidence: 99%

Pharmacological Evaluation and Docking Studies of 3-Thiadiazolyl- and Thioxo-1,2,4-triazolylcoumarin Derivatives as Cholinesterase Inhibitors

et al. 2012

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Inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) is considered a promising strategy for the treatment of Alzheimer's disease (AD). This research project aims to provide a comprehensive knowledge of newly synthesized coumarin analogues with anti-AD potential. In the present work a series of 3-thiadiazolyl- and thioxo-1,2,4-triazolylcoumarins derivatives were designed, synthesized, and tested as potent inhibitors of cholinesterases. These compounds were assayed against AChE from electrophorus electricus and rabbit; and BChE from horse serum and rabbit by Ellman's method using neostigmine methylsulphate and donepezil as reference drugs. Some of the assayed compounds proved to be potent inhibitors of AChE and BChE with Ki values in the micromolar range. 4b was found to be the most active compound with Ki value 0.028 ± 0.002 μM and higher selectivity for AChE/BChE. The ability of 4b to interact with AChE was further confirmed through computational studies, in which a primary binding was proved to occur at the active gorge site, and a secondary binding was revealed at the peripheral anionic site. Structure activity relationships of prepared compounds were also discussed.

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Section: Introductionmentioning

confidence: 99%

Pharmacological Evaluation and Docking Studies of 3-Thiadiazolyl- and Thioxo-1,2,4-triazolylcoumarin Derivatives as Cholinesterase Inhibitors

et al. 2012

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“…The acylhydrazones [(hydrazide-hydrazone (ACOANHA N‚CHA)] are classified as important functional group which exhibit significant role in anti-inflammatory (Todeschini et al, 1998;Radhwan et al, 2007;Gaston et al, 1996;Almasirad et al, 2005;Murineddu et al, 2001), antimalarial (Gemma et al, 2006), antimicrobial (Masunari and Tavares, 2007;Kuc¸ukguzel et al, 2002), anticonvulsant (Dimmock et al, 2000;Ragavendran et al, 2007), antitumor (Bernhardt et al, 2009;Whitnall et al, 2006;Vicini et al, 2006;Terzioglu and Gursoy, 2003;Abadi et al, 2003), analgesic (Lima et al, 2000), antiplatelet (Silva et al, 2004) and antitubercular (Vavrikova et al, 2011a;Manvar et al, 2008;Vavrikova et al, 2011b) activities. In recent years, researchers have turned their interest by replacing the central heterocyclic spacer of the bis(indole) alkaloids with biologically active long chain linkers such as glyoxylamide derivatives , and acylhydrazones and their cytotoxic activity was evaluated against human cancer cell lines (Kumar et al, 2012).…”

Section: Introductionmentioning

confidence: 98%

Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study

Choppara

Bethu

Prasad

et al. 2019

Arabian Journal of Chemistry

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Two series of novel bis(indole) analogues viz., N 0 -((5-substituted-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)alkanehydrazides (7a-f) and N 0 -((5-substituted-1-(3-methylbut-2-e nyl)-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)acetohydrazide (8a-f) were synthesized and characterized by spectral analysis. The target molecules were screened for their antimicrobial, anticancer activities and structure and activity relationship (SAR) was investigated. Compounds 7a, 7c and 8a were found to be active in antimicrobial screening. Anticancer screening reveals that Compound 7c was active against HeLa cell line with an IC 50 of 43.1 lM and compound 7d was found to be interesting candidate with an IC 50 of 26.0 and 30.2 lM against Colo-205 and Hep G2 cell lines respectively. ª 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

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“…Compound 4-adamantan-1-yl-quinoline-2-carboxylic acid (2-chlorobenzylidene) hydrazide [37] inhibited drug sensitive Mtb H37Rv and equipotent to INH (Nayyar et al, 2007). During the coumarin-4-acetic acid benzylidene hydrazides as anti-TB agents against Mtb H37Rv strain, (7-Hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid (3-nitro-benzylidene) hydrazide [38] was found to be most potent (Manvar et al, 2008). Some 5, 6, 7, 8-tetrahydronaphthalen acetic acid benzylidene hydrazide derivatives showed anti-TB activity and compounds having -OH and -NO 2 in ortho and Meta position of aromatic ring having high anti-TB activity (Ozemir et al, 2010).…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Pharmacologically potentials of hydrazonone containing compounds: a promising scaffold

Asif

2014

International Journal of Advanced Chemistry

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Synthesis, anti-tubercular activity and 3D-QSAR study of coumarin-4-acetic acid benzylidene hydrazides

Cited by 78 publications

References 18 publications

Pharmacological Evaluation and Docking Studies of 3-Thiadiazolyl- and Thioxo-1,2,4-triazolylcoumarin Derivatives as Cholinesterase Inhibitors

Pharmacological Evaluation and Docking Studies of 3-Thiadiazolyl- and Thioxo-1,2,4-triazolylcoumarin Derivatives as Cholinesterase Inhibitors

Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study

Pharmacologically potentials of hydrazonone containing compounds: a promising scaffold

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