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

doi:10.1016/j.bmcl.2011.12.014

PMID: 22197387DOI: 10.1016/j.bmcl.2011.12.014Dec 27, 2011

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

Bioorganic & Medicinal Chemistry Letters

Mohamed Jawed AhsanMd Shivli Nomani

Abstract

In search of potential therapeutics for tuberculosis, we describe herewith the synthesis, characterization and antimycobacterial activity 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 (4a) 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 3.12μg/mL, respectively, free from any cytotoxicity (>62.5μg/mL).

References

Does pyrazinoic acid as an active moiety of pyrazinamide have specific activity against Mycobacterium tuberculosis?

Aug 1, 1989·Antimicrobial Agents and Chemotherapy·L B HeifetsP J Lindholm-Levy

Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings

Mar 22, 2001·Advanced Drug Delivery Reviews·C A LipinskiP J Feeney

Citations

Substituted oxadiazoles: a patent review (2010 - 2012)

May 15, 2013·Expert Opinion on Therapeutic Patents·Afshin Zarghi, Zahra Hajimahdi

Synthesis and anticancer activity of N-aryl-5-substituted-1,3,4-oxadiazol-2-amine analogues

Jul 1, 2014·BioMed Research International·Mohamed Jawed AhsanSabina Yasmin

New structural classes of antituberculosis agents

Jun 10, 2017·Medicinal Research Reviews·Vajinder KumarRahul Jain

Nanofibrous matrixes with biologically active hydroxybenzophenazine pyrazolone compound for cancer theranostics

Mar 4, 2017·Materials Science & Engineering. C, Materials for Biological Applications·Subramani KandhasamyParamasivan T Perumal

Synthesis, Molecular Docking and β-Glucuronidase Inhibitory Potential of Indole Base Oxadiazole Derivatives

Mar 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·El Hassane AnouarAshik Mosaddik

Synthesis and biological evaluation of newer 1,3,4-oxadiazoles incorporated with benzothiazepine and benzodiazepine moieties.

Feb 10, 2017·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·Patel NavinGildardo Rivera

Anti-tuberculosis activity and its structure-activity relationship (SAR) studies of oxadiazole derivatives: A key review

Oct 9, 2020·European Journal of Medicinal Chemistry·Santosh Kumar VermaK P Rakesh

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Nov 26, 2019·European Journal of Medicinal Chemistry·Zefeng ZhaoXiaohui Zheng

Therapeutic potential of oxadiazole or furadiazole containing compounds

Dec 30, 2020·BMC Chemistry·Ankit Siwach, Prabhakar Kumar Verma

Related Concepts

Antitubercular Agents

Cercopithecus tantalus

Dose-Response Relationship, Drug

Fungus Drug Sensitivity Tests

Mycobacterium tuberculosis H37Rv

Pyrazoles

Structure-Activity Relationship

Vero Cells

Tuberculosis, Drug-Resistant

Antitubercular Agents

Related Feeds

Antitubercular Agents (ASM)

Antitubercular agents are pharmacologic agents for treatment of tuberculosis. Discover the latest research on antitubercular agents here.

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antifungals

Antitubercular Agents

Antitubercular agents are pharmacologic agents for treatment of tuberculosis. Discover the latest research on antitubercular agents here.

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

Abstract

References

Does pyrazinoic acid as an active moiety of pyrazinamide have specific activity against Mycobacterium tuberculosis?

Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings

Citations

Substituted oxadiazoles: a patent review (2010 - 2012)

Synthesis and anticancer activity of N-aryl-5-substituted-1,3,4-oxadiazol-2-amine analogues

New structural classes of antituberculosis agents

Nanofibrous matrixes with biologically active hydroxybenzophenazine pyrazolone compound for cancer theranostics

Synthesis, Molecular Docking and β-Glucuronidase Inhibitory Potential of Indole Base Oxadiazole Derivatives

Synthesis and biological evaluation of newer 1,3,4-oxadiazoles incorporated with benzothiazepine and benzodiazepine moieties.

Anti-tuberculosis activity and its structure-activity relationship (SAR) studies of oxadiazole derivatives: A key review

Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect

Therapeutic potential of oxadiazole or furadiazole containing compounds

Related Concepts

Related Feeds

Antitubercular Agents (ASM)

Antifungals (ASM)

Antifungals

Antitubercular Agents

Related Papers

Molecular properties prediction and synthesis of novel 1,3,4-oxadiazole analogues as potent antimicrobial and antitubercular agents

Synthesis and antiviral activity of 4,4'-(arylmethylene)bis(1H-pyrazol-5-ols) against peste des petits ruminant virus (PPRV)

3-Aryl-4-(arylhydrazono)-1H-pyrazol-5-ones: Highly ligand efficient and potent inhibitors of GSK3beta

Synthesis and biological activity of N,N-dialkylaminoalkyl-substituted bisindolyl and diphenyl pyrazolone derivatives

Insecticidal lead identification by screening benzopyrano[4,3-c] pyrazol-3(2H)-ones library constructed from multiple-parallel synthesis under microwave irradiation