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

• Published in: Chemical papers Vol. 77; no. 7; pp. 3791 - 3802
• Main Authors: Shinde, Abhijit, Thakare, Prashant P., Nandurkar, Yogesh, Chavan, Abhijit, Shaikh, Abdul Latif N., Mhaske, Pravin C.
• Format: Journal Article
• Language: English
• Published: Cham Springer International Publishing 01-07-2023
• Subjects: Biochemistry; Biotechnology; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Industrial Chemistry/Chemical Engineering; Materials Science; Medicinal Chemistry; Original Paper; Quinoline; Antimicrobial activity; Antitubercular activity
• ISSN: 0366-6352; 1336-9075; 2585-7290
• DOI: 10.1007/s11696-023-02741-3

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