Synthesis of 2-(6-substituted quinolin-4-yl)-1-alkoxypropan-2-ol as potential antimycobacterial agents

Abhijit Shinde; Prashant P Thakare; Yogesh Nandurkar; Abhijit Chavan; Abdul Latif N Shaikh; Pravin C Mhaske

doi:10.1007/s11696-023-02741-3

Synthesis of 2-(6-substituted quinolin-4-yl)-1-alkoxypropan-2-ol as potential antimycobacterial agents

Chem Zvesti. 2023;77(7):3791-3802. doi: 10.1007/s11696-023-02741-3. Epub 2023 Feb 25.

Authors

Abhijit Shinde¹, Prashant P Thakare¹, Yogesh Nandurkar^{1

2}, Abhijit Chavan¹, Abdul Latif N Shaikh^{1

3}, Pravin C Mhaske¹

Affiliations

¹ Department of Chemistry, S. P. Mandali's Sir Parashurambhau College (Affiliated to, Savitribai Phule Pune University), Tilak Road, Pune, 411030 India.
² Department of Chemistry, N. Wadia College (Affiliated to Savitribai Phule Pune University), Pune, India.
³ Department of Chemistry, Jijamata College of Science and Arts (Affiliated to Savitribai Phule Pune University), Bhende, Ahmednagar, India.

Abstract

Resistance to antibiotic drugs has directed global health security to a life-threatening situation due to mycobacterial infections. In search of a new potent antimycobacterial, a series of (±) 2-(6-substituted quinolin-4-yl)-1-alkoxypropan-2-ol (8a-p) have been synthesized. The structures of the newly synthesized derivatives were characterized by spectrometric analysis. Derivatives 8a-p were evaluated for antitubercular activity against Mycobacterium tuberculosis H37Rv (ATCC 25177), antibacterial activity against Proteus mirabilis (NCIM2388), Escherichia coli (NCIM 2065), Bacillus subtilis (NCIM2063) Staphylococcus albus (NCIM 2178) and antifungal activity against Candida albicans (NCIM 3100), Aspergillus niger (ATCC 504). Thirteen 2-(6-substituted quinolin-4-yl)-1-alkoxypropan-2-ol (8a-m) derivatives reported moderate to good antitubercular activity against M. tuberculosis H37Rv with MIC 9.2-106.4 μM. Compounds 8a and 8h showed comparable activity with respect to the standard drug pyrazinamide. The active compounds screened for cytotoxicity activity against L929 mouse fibroblast cells showed no significant cytotoxic activity. Compounds 8c, 8d, 8e, 8g, 8k, and 8o displayed good activity against S. albus. Compounds 8c and 8n showed good activity against P. mirabilis and E. coli, respectively. The potential antimycobacterial activities imposed that the 2-(6-substituted quinolin-4-yl)-1-alkoxypropan-2-ol derivatives could lead to compounds that could treat tuberculosis.

Supplementary information: The online version contains supplementary material available at 10.1007/s11696-023-02741-3.

Keywords: Antimicrobial activity; Antitubercular activity; Quinoline.

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