Synthesis and Bioactivity Assessment of <i>N</i>-Aryl-Azasesamins
Jiri Wu,
Xubing Qi,
Yogini S. Jaiswal,
Cui Lin,
Xun Song,
Xinrong Xie,
Shaoyang Su,
Yifu Guan,
Leonard L. Williams,
Hedong Bian
Affiliations
Jiri Wu
Key Laboratory of Chemistry and Engineering of Forest Products (State Ethnic Affairs Commission), Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006, China
Xubing Qi
Key Laboratory of Chemistry and Engineering of Forest Products (State Ethnic Affairs Commission), Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006, China
Yogini S. Jaiswal
Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, The North Carolina Research Campus, Kannapolis, NC 28081, USA
Cui Lin
Surgery Room, Yulin First People’s Hospital, Yulin 537000, China
Xun Song
College of Pharmacy, Shenzhen Technology University, Shenzhen 518118, China
Xinrong Xie
Key Laboratory of Chemistry and Engineering of Forest Products (State Ethnic Affairs Commission), Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006, China
Shaoyang Su
Department of Applied Chemistry Teaching and Research, Guangxi Vocational University of Agriculture, Nanning 530007, China
Yifu Guan
Key Laboratory of Chemistry and Engineering of Forest Products (State Ethnic Affairs Commission), Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006, China
Leonard L. Williams
Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, The North Carolina Research Campus, Kannapolis, NC 28081, USA
Hedong Bian
Key Laboratory of Chemistry and Engineering of Forest Products (State Ethnic Affairs Commission), Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006, China
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.
