Synthesis and antitubercular activity of 4-(3-coumarinyl)-3-cyclohexyl-4-thiazolin-2-one benzylidenehydrazones

Karalı, Nilgün; Kocabalkanli, Ayse; Gürsoy, Aysel; Ateş, Öznur

doi:10.1016/s0014-827x(02)01254-5

Cited by 44 publications

(27 citation statements)

References 8 publications

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“…The synthesized benzohydrazides were potent antimicrobial and anticancer agents 13 . Numbers of hydrazide-hydrazone derivatives possess antituberculosis activity [14][15][16][17][18][19][20][21] . The present study is aimed to carry out design, synthesis, in silico and in-vitro antimicrobial studies for the series of benzoic acid (4-allyloxy-benzylidene)-hydrazides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Anti Mycobacterial Activity of Novel Hydrazones

S¹,

Geethamalika²

2017

Orient. J. Chem

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The hydrazone Schiff base analogues namely benzoic acid (4-allyloxy-benzylidene)-hydrazide and its series were designed and synthesized. The structures of newly synthesized compounds were characterized by analytical methods and spectral analysis and subjected to antibacterial and docking studies. The synthesized molecules were subjected to molecular docking studies using enoyl-acyl-carrier protein reductase (NADH) from mycobacterium tuberculosis as the receptor. The docking results confirm the binding affinity of the synthesized compounds with the selected receptor. Preliminary in-vitro anti bacterial studies were carried out with Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Benzoic acid (4-allyloxy-benzylidene)-hydrazide was found to be most potent anti tuberculosis agent at 200 and 100µg per ml, the percentage of inhibition was 98.7% and 97.9%. The designed synthesized molecules were considered for evaluation for the molecular docking studies of their binding pattern with enoyl-acyl-carrier protein reductase from Mycobacterium tuberculosis. The antimycobacterial screening was performed against MTB H37Rv an isoniazid-resistant clinical isolate of MTB was used for the study.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Anti Mycobacterial Activity of Novel Hydrazones

S¹,

Geethamalika²

2017

Orient. J. Chem

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“…Strains 7,12 , such as coumarins, which are characterized for being formed by the fusion between benzene and α-pyrone rings 13 , and are widely used according to their biological MOL2NET, 2017, 3, doi:10.3390/mol2net-03-xxxx 3 potentialities, highlighting as antibacterial 14 , antifungal 15 , anti-inflammatory 16 , antitumor 17 , anticoagulant 18 , antimycobacterial 19 , among others.…”

Section: Introductionmentioning

confidence: 99%

<strong>Synthesis and Anti-mycobacterial evaluation of coumarin derivatives</strong>

Araújo

Luna

Montenegro

et al. 2017

Proceedings of MOL2NET 2017, International Conference on Multidisciplinary Sciences, 3rd Edition

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“…The methods of investigation of structure-activity relationships (SARs) enabled us to find some new pharmacophores of the above-mentioned activity. Many studies were carried out on heterocyclic systems bearing a hydrazone structure as a pharmacophore (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13). In this study, we planned to synthesize new molecules bearing hydr azone moieties for their potential antituberculosis activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some novel hydrazone derivatives and evaluation of their antituberculosis activity

Özdemir¹,

Kaplancıklı²,

Turan³

et al. 2010

mpj

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INTRODUCTIONIn spite of a 5000 year history, tuberculosis (TB) remains the leading single-agent infectious disease killer in the world. Approximately one third of the world's population is infected with TB bacilli, and each year almost 8 million people develop active TB and 2 million die as a result of TB. The major challenges for tuberculosis control are the development of multidrug-resistant tuberculosis (MDRTB) strains and the increasing numbers of immunocompromised individuals with HIV infections who are highly susceptible to the disease. As a result, there is a pressing need for new antitubercular agents acting with greater potency and efficacy than the current existing drugs (1).To pursue this goal, our research efforts are directed to find new chemical classes of antimycobacterially active agents. The methods of investigation of structure-activity relationships (SARs) enabled us to find some new pharmacophores of the above-mentioned activity. Many studies were carried out on heterocyclic systems bearing a hydrazone structure as a pharmacophore (2-13). In this study, we planned to synthesize new molecules bearing hydr azone moieties for their potential antituberculosis activity. ChemistryThe synthetic route of the compounds is outlined in Scheme 1. For the synthesis of the title compounds, 5,6,7,8-tetrahydronaphthalene acetic acid hydrazide required as starting material was prepared by the reaction of 5,6,7,8-tetrahydronaphthalene acetic acid ethyl ester with hydrazine hydrate (14). The reaction of equimolar quantities of hydrazide with appropriate benzaldehydes in the presence of isopropyl alcohol resulted in the formation of the title compounds (A1-15) ( Table 1). Pharmacology Antituberculosis activity and CytotoxicityThe initial screen is conducted against Mycobacterium tuberculosis H37Rv (ATCC 27294) in BACTEC 12B medium using the Microplate Alamar Blue Assay (MABA) (15). One of the compounds showed significant antituberculosis activity as can be inferred from Table 2.The VERO cell cytotoxicity assay (16) is done in parallel with the TB Dose Response assay. Viabil-ABSTRACT: The heterocyclic hydrazone constitute an important class of biologically active drug molecules which have attractive attention of medicinal chemists due to their antituberculosis activities. For this purpose, new hydrazone derivatives were synthesized and evaluated for antituberculosis activity. The reaction of (5,6,7,8-tetrahydronaphthalen-1-yl) acetic acid hydrazide with various benzaldehydes gave 5,6,7,8-tetrahydronaphtalen acetic acid benzylidene hydrazide derivatives. The chemical structures of the compounds were elucidated by 1H-NMR, EI-MS spectral data and Elemental Analysis. The compounds were evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC 27294) using the BACTEC 460 radiometric system and BACTEC 12B medium. The preliminary results indicated that all of the tested compounds showed low activity against the test organism. The compound A10 showed high antituberculosis activity (IC50: 3.07...

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Synthesis and antitubercular activity of 4-(3-coumarinyl)-3-cyclohexyl-4-thiazolin-2-one benzylidenehydrazones

Cited by 44 publications

References 8 publications

Synthesis, Characterization and Anti Mycobacterial Activity of Novel Hydrazones

Synthesis, Characterization and Anti Mycobacterial Activity of Novel Hydrazones

<strong>Synthesis and Anti-mycobacterial evaluation of coumarin derivatives</strong>

Synthesis of some novel hydrazone derivatives and evaluation of their antituberculosis activity

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