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In this study, certain 3‐substituted styrylquinoxalin‐2(1H)‐ones (2a‐d) and their 2‐chloro (3a‐d) and 2‐piperazinyl derivatives (4a‐g) were synthesized from 3‐methylquinoxalin‐2(1H)‐one (1). In addition, a series of 1‐alkyl‐3‐substituted styrylquinoxalin‐2(1H)‐ones (5a‐d) was also prepared. Moreover, 3‐(N2‐arylidenehydrazinocarbonyl)quinoxalin‐2(1H)‐ones (8a‐c) as well as their cyclized oxadiazolinyl derivatives (9a‐c) were prepared from 3‐hydrazinocarbonylquinoxalin‐2(1H)‐one (7). Furthermore, 3‐(5‐substituted thio‐1,3,4‐oxadiazol‐2‐yl)quinoxalin‐2(1H)‐ones (11a‐c) and (12a‐c) were obtained from the intermediate compound (10) ‐ previously obtained via cyclization of (7) with CS2. Likewise, 3‐(5‐oxo‐4,5‐dihydro‐(1,3,4‐oxadiazol‐2‐yl)quinoxalin‐2(1H)‐one (13), 3‐[5‐(4‐nitrophenyl)‐1,3,4‐oxadiazol‐2‐yl]‐quinoxalin‐2(1H)‐one (14) and its 2‐chloro derivative (15) were prepared from 3‐hydrazinocarbonylquinoxalin‐2(1H)‐one (7). Some of these derivatives were evaluated for antimicrobial activity in vitro and some of the tested compounds showed antibacterial or antifungal activity.

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New ecofriendly Biginelli reaction procedures have been adapted to prepare new dihydropyrimidines (DHPMs) using a multicomponent one-pot reaction. All the synthesized compounds were evaluated for their anticancer activity against 59 human cancer cell lines and evaluated for their antimicrobial activities against representatives of both Gram-positive and Gram-negative bacteria. Compound 4 showed marked wide spectrum anticancer activity towards most of the tested cancer cell lines with a percentage of growth inhibition of 29.04-71.68% against leukemia cell line (K-562 and SR), lung cancer cell line (NCI-H522), five colon cancer cell lines (HCT-116, HCT-15, HT29, KM12 and SW-620), CNS cancer cell line (SF-295 and SNB-75), melanoma cell lines (MALME-3M and M14), renal cancer cell line (CAKI-1) and breast cancer cell lines (MCF7 and MDA-MB-468). The highest observed anticancer activity was against leukemia cell lines K-562 and SR with inhibition percentages of 64.97 and 71.68%, respectively. The renal cancer cell line (UO-31) was particularly sensitive towards all the evaluated compounds. Compounds including 2b and 5c exhibited antibacterial activity against S. aureus while 2a and 5b exhibited antifungal activity against C. albicans. The results also showed that compounds 2c and 5e exhibited both antibacterial and antifungal activity against S. aureus and C. albicans respectively.