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Seeking potent anti-tubercular agents: design and synthesis of substituted-N-(6-(4-(pyrazine-2-carbonyl)piperazine/homopiperazine-1-yl)pyridin-3-yl)benzamide derivatives as anti-tubercular agents. 2020

Singireddi Srinivasarao, and Adinarayana Nandikolla, and Amaroju Suresh, and Kevin Van Calster, and Linda De Voogt, and Davie Cappoen, and Balaram Ghosh, and Himanshu Aggarwal, and Sankaranarayanan Murugesan, and Kondapalli Venkata Gowri Chandra Sekhar
Department of Chemistry, Birla Institute of Technology and Science, Pilani Hyderabad Campus, Jawahar Nagar, Kapra Mandal Hyderabad-500078 Telangana India kvgc@hyderabad.bits-pilani.ac.in kvgcs.bits@gmail.com +91 40 66303527.

Pyrazinamide is an important first-line drug used in shortening TB therapy. In our current work, a series of novel substituted-N-(6-(4-(pyrazine-2-carbonyl)piperazine/homopiperazine-1-yl)pyridin-3-yl)benzamide derivatives were designed, synthesized, and evaluated for their anti-tubercular activity against Mycobacterium tuberculosis H37Ra. Among the tested compounds, five compounds (6a, 6e, 6h, 6j and 6k) from Series-I and one compound (7e) from Series-II exhibited significant activity against Mycobacterium tuberculosis H37Ra with 50% inhibitory concentrations (IC50) ranging from 1.35 to 2.18 μM. To evaluate the efficacy of these compounds, we examined their IC90 values. Five of the most active compounds were found to be more active with IC90s ranging from 3.73 to 4.00 μM and one compound (6e) showed an IC90 of 40.32 μM. Moreover, single crystals were developed for 6d, 6f and 6n. In addition, most active compounds were evaluated for their cytotoxicity on HEK-293 (human embryonic kidney) cells. Our results indicate that the compounds are nontoxic to human cells. The molecular interactions of the derivatised conjugates in docking studies reveal their suitability for further development.

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