Design and synthesis of oxaprozin‐1,3,4‐oxadiazole hybrids as potential anticancer and antibacterial agents

Abstract

In the present study, we report design, synthesis and screening of new novel 5‐substituted‐2‐mercapto‐1,3,4‐oxadiazole analogues appended to oxaprozin for their in vitro anticancer and antibacterial activity. The synthesised compounds were characterized using various spectroscopic techniques. Furthermore, the structure of 5b (2‐(2‐[4,5‐diphenyloxazol‐2‐yl]ethyl)‐5‐(ethylthio)‐1,3,4‐oxadiazole) was unequivocally confirmed by X‐ray analysis. Among the series 5c (2‐(2‐[4,5‐diphenyloxazol‐2‐yl]ethyl)‐5‐(propylthio)‐1,3,4‐oxadiazole) showed most promising anticancer activity against A549 cancer cell line and all the reported analogues manifested satisfactory safety profiles against human normal cell line HEK293T. The products exhibited good antibacterial activity and among the tested 5j (2‐(2‐[4,5‐diphenyloxazol‐2‐yl]ethyl)‐5‐([4‐fluorobenzyl]thio)‐1,3,4‐oxadiazole) exhibited most potent.

An Overview of Recent Advances in Biomedical Applications of Click Chemistry

“…Doxorubicin was taken as a reference compound. Among the tested series of compounds, compound 8e with two methyl groups at positions of 2 and 4 of the phenyl rings demonstrated the best anticancer activity with IC 50 of 27.50 and 31.03 μg/mL against HeLa and MCF-7 cancer cell lines, respectively, as compared to Doxorubicin (IC 50 = 6.43 and 8.66 μg/mL) …”

“…Among the tested series of compounds, compound 8e with two methyl groups at positions of 2 and 4 of the phenyl rings demonstrated the best anticancer activity with IC 50 of 27.50 and 31.03 μg/mL against HeLa and MCF-7 cancer cell lines, respectively, as compared to Doxorubicin (IC 50 = 6.43 and 8.66 μg/mL). 79 In addition to this, Singh and co-workers have also used the efficient click chemistry method to develop a new series of coumarins conjugated with different C5-curcuminoid motifs as potential anticancer agents (Figure 7). Among all conjugates developed, 7-methylcoumarin-1,2,3triazole-2-methyl benzimidazole hybrid (33) exhibited the strongest cytotoxicity against HepG2 cells with an IC 50 value of 0.9 μM.…”

In Vitro Evaluation of Antimicrobial Properties of Some New 1, 3, 4-Oxadiazole Derivatives against Acinetobacter baumannii

“…Both methods involve the release of N 2 . In recent years 1, 3, 4-Oxadiazole compounds have been reported to exhibit antibacterial [15] , antifungal [16] , anti-tubercular [17] , anti-inflammatory [18] and anticancer [19] activities. Objectives: As synthesis and evaluation of antimicrobial activity was an important part of this research program [20] ; herein, antibacterial activities of 1, 3, 4-Oxadiazole derivatives against A.baumannii PTCC1855 were evaluated.…”