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Synthesis of novel 5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline-6-carboxamides as potent inhibitors of Mycobacterium tuberculosis

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Abstract

A series of novel 5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline-6-carboxamides was designed, synthesized, and evaluated for antitubercular activity. The required 5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline-6-carboxylic acid intermediate was prepared by oxidizing the respective aldehyde with sodium chlorite and 30% H2O2. Further, the acid was coupled with various aryl, alkyl, and heterocyclic amines using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and hydroxybenzotriazole to give the desired 5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline-6-carboxamides in excellent yields. All the new compounds were characterized by their NMR and mass spectral analysis. Screening of all new compounds for in vitro antimycobacterial activity against M. tuberculosis H37Rv (Mtb) resulted in five analogs with MIC 3.12 µg/cm3 as promising antitubercular agents with lower cytotoxicity profiles.

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Acknowledgements

Authors thank Indo-Russia DST-RFBR collaborative project (INT/RUS/RFBR/P-296) for financial support. SKM is thankful to UGC for senior research fellowship. CSIR-IICT communication no. IICT/Pubs./2019/045.

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Authors and Affiliations

  1. Fluoro and Agrochemicals Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, 500007, India

    Sandeep Kumar Marvadi, Devendra Nagineni, Syeda Safoora & Srinivas Kantevari

  2. Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology and Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India

    Vagolu Siva Krishna & Dharmarajan Sriram

  3. Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, 500007, India

    Srinivas Kantevari

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  1. Sandeep Kumar Marvadi
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  2. Devendra Nagineni
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  3. Syeda Safoora
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  4. Vagolu Siva Krishna
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  5. Dharmarajan Sriram
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  6. Srinivas Kantevari
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Correspondence to Srinivas Kantevari.

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Marvadi, S.K., Nagineni, D., Safoora, S. et al. Synthesis of novel 5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline-6-carboxamides as potent inhibitors of Mycobacterium tuberculosis. Monatsh Chem 151, 405–415 (2020). https://doi.org/10.1007/s00706-020-02560-2

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  • DOI: https://doi.org/10.1007/s00706-020-02560-2

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