Discovery of novel antitubercular 1,5-dimethyl-2-phenyl-4-([5-(arylamino)-1,3,4-oxadiazol-2-yl]methylamino)-1,2-dihydro-3H-pyrazol-3-one analogues

Ahsan, Mohamed Jawed; Samy, Jeyabalan Govinda; Jain, Chandra Bhushan; Dutt, K. R.; Khalilullah, Habibullah; Nomani, Md. Shivli

doi:10.1016/j.bmcl.2011.12.014

Cited by 55 publications

(16 citation statements)

References 22 publications

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“…In search of potential therapeutics for tuberculosis, Ahsan et al [54] has synthesized a series of 1,5-dimethyl-2-phenyl-4-([5-(arylamino)-1,3,4-oxadiazol-2-yl]methylamino)-1,2-dihydro-3H-pyrazol-3-one analogues. Among the synthesized compounds, 4-[(5-[(4-fluorophenylamino]-1,3,4-oxadiazol-2-yl)methylamino]-1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3-one (70) was found to be the most promising compound active against Mycobacterium tuberculosis H 37 Rv and isoniazid resistant M. tuberculosis with minimum inhibitory concentrations, 0.78 and 3.12 g/mL respectively and free from any cytotoxicity (>62.5 g/mL).…”

Section: Antibacterial Antimycobecterial and Antifungal Activitiesmentioning

confidence: 99%

1,3,4-Oxadiazole: A Biologically Active Scaffold

Khalilullah

Ahsan²,

Hedaitullah³

et al. 2012

MRMC

123

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There has been considerable interest in the development of novel compounds with anticonvulsant, antidepressant, analgesic, anti-inflammatory, antiallergic, antipsychotic, antimicrobial, antimycobecterial, antitumour, antiviral and antitubercular activities. 1,3,4-oxadiazoles constitute an important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. These observations led to the development of new 1,3,4-oxadiazole derivatives. This review article describes the various biological activities associated with 1,3,4-oxadiazole ring system and is useful in guiding the researchers across the world working on this moiety and consequently have been instrumental in the advancement of 1,3,4-oxadiazole chemistry.

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Section: Antibacterial Antimycobecterial and Antifungal Activitiesmentioning

confidence: 99%

1,3,4-Oxadiazole: A Biologically Active Scaffold

Khalilullah

Ahsan²,

Hedaitullah³

et al. 2012

MRMC

123

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“…methoxyphenyl, 2-methylphenyl, 3-methylphenyl and 4methylphenyl exhibited less inhibition. In the follow up research [115], the potent compound 160 (Fig. 15) was selected from the novel synthesized analogues with excellent activity and free from cytotoxicity (>62.5 mg/mL) appeared.…”

Section: Anti-tuberculosis Agentsmentioning

confidence: 99%

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Zhao

Dai

et al. 2020

European Journal of Medicinal Chemistry

136

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a b s t r a c tThe pyrazolone structural motif is a critical element of drugs aimed at different biological end-points. Medicinal chemistry researches have synthesized drug-like pyrazolone candidates with several medicinal features including antimicrobial, antitumor, CNS (central nervous system) effect, anti-inflammatory activities and so on. Meanwhile, SAR (Structure-Activity Relationship) investigations have drawn attentions among medicinal chemists, along with a plenty of analogues have been derived for multiple targets. In this review, we comprehensively summarize the biological activity and SAR for pyrazolone analogues, wishing to give an overall retrospect and prospect on the pyrazolone derivatives.

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“…The resulting compound 132 displayed MIC values of 0.78 μg/mL and 3.12 μg/mL against M. tuberculosis H37Rv and isoniazid‐resistant M. tuberculosis , respectively. The cytotoxicity assay on the Vero cells showed 132 to be nontoxic up to a concentration of 62.5 μg/mL . Benzimidazole‐based 1,3,4‐oxadiazoles also showed potential as new anti‐TB scaffolds.…”

Section: Oxadiazolesmentioning

confidence: 99%

New structural classes of antituberculosis agents

Kumar

Patel

Jain

2017

Medicinal Research Reviews

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Tuberculosis (TB), one of the deadliest diseases is shattering the health and socioeconomic status of the society. The emergence of multidrug resistant (MDR) and extremely drug resistant (XDR) strains has provided unprecedented lethal character to TB. The development of MDR and XDR strains of TB results in more deaths, longer duration of therapy, and appearance of the disease in the immunocompromised patients. Because of the development of rapid resistance by Mycobacterium tuberculosis, researchers are confronted with serious challenges in combating TB. For instance, the need for potency and specificity in therapeutic agents approaching clinics, and the increasing demand of low toxicity due to long duration of treatment. Recently, it is proposed that such challenges could be addressed by a shift from contemporary or known classes of drugs to new scaffold-containing or entirely new structural classes of drugs that possibly act on the previously unknown targets, resulting in possibly less instances of resistance development. The exploitation of advances made in the biology of TB in the last and present decades have created opportunities to discover a large number of new structural classes that specifically targets TB by molecular mechanism of action(s) unknown earlier. We have earlier reviewed new structural classes of anti-TB agents up to year 2005. This review covers literature reports of the subsequent 10 years on the discovery of new structural classes of synthetic anti-TB agents. Due to the availability of large number of research reports, we have divided new compounds in 38 structural classes, 368 structures, and 307 references.

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Discovery of novel antitubercular 1,5-dimethyl-2-phenyl-4-([5-(arylamino)-1,3,4-oxadiazol-2-yl]methylamino)-1,2-dihydro-3H-pyrazol-3-one analogues

Cited by 55 publications

References 22 publications

1,3,4-Oxadiazole: A Biologically Active Scaffold

1,3,4-Oxadiazole: A Biologically Active Scaffold

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

New structural classes of antituberculosis agents

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