Synthesis, computational studies, antimycobacterial and antibacterial properties of pyrazinoic acid–isoniazid hybrid conjugates

Siva S. Panda; Adel S. Girgis; Bibhuti B. Mishra; Mohamed Elagawany; Venkatasai Devarapalli; William F. Littlefield; Ahmed Samir; Walid Fayad; Nehmedo G. Fawzy; Aladdin M. Srour; Riham M. Bokhtia

doi:10.1039/C9RA03380G

Synthesis, computational studies, antimycobacterial and antibacterial properties of pyrazinoic acid–isoniazid hybrid conjugates†

Siva S. Panda,

*^a Adel S. Girgis,

*^b Bibhuti B. Mishra,^c Mohamed Elagawany,^ad Venkatasai Devarapalli,^a William F. Littlefield,^a Ahmed Samir,^e Walid Fayad,^f Nehmedo G. Fawzy,^b Aladdin M. Srour^g and Riham M. Bokhtia^ah

Author affiliations

* Corresponding authors

^a Department of Chemistry & Physics, Augusta University, Augusta, GA 30912, USA
E-mail: sspanda12@gmail.com

^b Department of Pesticide Chemistry, National Research Centre, Dokki, Giza 12622, Egypt
E-mail: girgisas10@yahoo.com

^c Department of Immunology and Microbial Disease, Albany Medical College, 47 New Scotland Avenue, Albany, NY-12208, USA

^d Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Damanhour University, Damanhour, Egypt

^e Microbiology Department, Faculty of Veterinary Medicine, Cairo University, Cairo, Egypt

^f Drug Bioassay-Cell Culture Laboratory, Pharmacognosy Department, National Research Centre, Dokki, Giza, Egypt

^g Department of Therapeutic Chemistry, National Research Centre, Dokki, Giza 12622, Egypt

^h Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt

Abstract

Benzotriazole and microwave mediated syntheses led to a new set of hybrid conjugates of pyrazinoic acid with isoniazid via amino acid linkers in excellent yields with retention of chirality. Microbiological screening of the synthesized conjugates revealed an exceptionally high activity against some of the pathogenic bacterial strains at low concentrations. Promising antimycobacterial properties were observed against tuberculous and non-tuberculous mycobacteria. Robust molecular models (2D-QSAR and 3D-pharmacophore) support the observed biological properties. Safety profile of the synthesized conjugates against human normal cell (RPE1) was evaluated by MTT technique.

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Synthesis, computational studies, antimycobacterial and antibacterial properties of pyrazinoic acid–isoniazid hybrid conjugates†

Abstract

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Synthesis, computational studies, antimycobacterial and antibacterial properties of pyrazinoic acid–isoniazid hybrid conjugates

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