Synthesis of Novel 3-Subtituted-2-Thioxo-2,3-Dihydroquinazolin-4(1H)-One Derivatives Via the Cascade Reaction and Investigation of Their In Situ Antimicrobial Activity on Candida albicans.

Dao, N. T.; Van, B. L.; Polyakova, E. I.; Le, T. A.

In the present study, we report a facile synthesis of a new series of 3-subtituted-2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives via the cascade reaction of various isothiocyanate derivatives and anthranilic acid. The reaction was assisted by microwave irradiation and finished after 1 h affording the target products with the yield within the range 40–72%. The synthetic compounds were characterized by spectroscopic methods including IR, NMR (1H, 2D, and 13C), and mass spectrometry. All spectral data indicated good accordance with expected structures. In addition, the complex of quinazoline derivatives with Candida albicans dihydrofolate reductase (C. albicans DHFR) were studied in silico. The results showed that all quinazoline compounds (2a–f) have a greater ability to inhibit C. albicans DHFR than 5-(phenylsulfanyl)-2,4-quinazolinediamine. Therefore, they are promising candidates for further studies in finding the lead structure for antimicrobial activity.

CANDIDA albicans; ANTI-infective agents; TETRAHYDROFOLATE dehydrogenase; AMINOBENZOIC acids; QUINAZOLINE

Pharmaceutical Chemistry Journal, 2023, Vol 57, Issue 9, p1401

0091-150X

Academic Journal

10.1007/s11094-023-03003-y