ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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, and Pravin C. Mhaske

Department of Chemistry, S. P. Mandali’s Sir Parashurambhau College (Affiliated to, Savitribai Phule Pune University), Pune, India

E-mail: mhaskepc18@gmail.com

Received: 3 October 2022  Accepted: 17 February 2023

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.

Graphical abstract

Keywords: Quinoline; Antitubercular activity; Antimicrobial activity

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-02741-3

Chemical Papers 77 (7) 3791–3802 (2023)