Synthesis and Bioactivity Assessment of N -Aryl-Azasesamins.

Wu, Jiri; Qi, Xubing; Jaiswal, Yogini S.; Lin, Cui; Song, Xun; Xie, Xinrong; Su, Shaoyang; Guan, Yifu; Williams, Leonard L.; Bian, Hedong

Sesamin, a tetrahydrofuran lignan, has gained significant attention over the past few decades due to its versatile medicinal activities. However, until now, the research on sesamin analogues has not been explored extensively. In this study, a series of new N-aryl-azasesamins were synthesized for the first time using sesamin as a raw material. The mechanism of the key breakage of the ethereal bond of the tetrahydrofuran ring in sesamin has been studied. The configuration of C6 in N-aryl-azasesamins was confirmed through NMR and X-ray single crystal refraction analyses. The results showed that the configuration of N-aryl-azasesamins was opposite to sesamin in C6. Subsequently, the N-aryl-azasesamins were evaluated for their antifungal and antitumor activities via micro-broth dilution and MTT assays. It was observed that none of the N-aryl-azasesamins exhibited inhibitory activity against the growth of C. albicans and C. neoformans at a concentration of 100 μg/mL. Most analogues showed no activity against HepG2 cells. However, 21c and 21k demonstrated antitumor activity after 24 h of incubation with IC50 values of 6.49 μM and 4.73 μM, respectively. These results suggest that some N-aryl-azasesamins exhibit significantly enhanced antitumor activity compared with sesamin.

SESAMIN; ANTINEOPLASTIC agents; SINGLE crystals; PYRROLIDINE; TETRAHYDROFURAN

Chemistry (2624-8549), 2024, Vol 6, Issue 6, p1347

2624-8549

Academic Journal

10.3390/chemistry6060079