Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives
Deng, Guogang1,2; Zhou, Bei1,2,4; Wang, Jing1,2; Chen, Zhuo1,2; Gong, Liang3; Gong, Yaxiao3; Wu, Dongmei3; Li, Yan3; Zhang, Hongbin1,2; Yang, Xiaodong1,2
Corresponding AuthorLi, Yan(liyanb@mail.kib.ac.cn) ; Zhang, Hongbin(zhanghb@ynu.edu.cn) ; Yang, Xiaodong(xdyang@ynu.edu.cn)
2019-04-15
Source PublicationEUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
ISSN0223-5234
Volume168Pages:232-252
AbstractSixty-one novel steroidal imidazolium salt derivatives were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results showed that diosgenin-imidazolium salt derivatives displayed much higher cytotoxic activities than cholesterol-imidazolium salts and dehydroepiandrosterone-imidazolium salts. The SARs results suggested that the existence of substituted 5,6-dimethyl-benzimidazoles or benzimidazole ring and substitution of the imidazolyl-3 alpha-position with a 2-bromobenzyl or 2-naphthylmethyl group could be critical for promoting cytotoxic activity. Diosgenin-imidazolium salt a30 was found to be the most potent compound with IC(50 )values of 0.44-0.79 mu M against five human tumor cell lines. Compound a24 showed inhibitory activity selectively against SMMC7721 cell lines with IC50 value of 0.21 mu M and 54-fold more sensitive to DDP. Moreover, compound a30 inhibited cell proliferation through inducing the G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells. (C) 2019 Elsevier Masson SAS. All rights reserved.
KeywordDiosgenin Cholesterol Dehydroepiandrosterone Imidazolium salt Antitumor activities Structure-activity relationships
DOI10.1016/j.ejmech.2019.02.025
Indexed BySCI
Language英语
WOS Research AreaPharmacology & Pharmacy
WOS SubjectChemistry, Medicinal
WOS IDWOS:000463120300018
Citation statistics
Cited Times:1[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/67598
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorLi, Yan; Zhang, Hongbin; Yang, Xiaodong
Affiliation1.Yunnan Univ, Key Lab Med Chem Nat Resource, Minist Educ, Kunming 650091, Yunnan, Peoples R China
2.Yunnan Univ, Sch Chem Sci & Technol, Kunming 650091, Yunnan, Peoples R China
3.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Yunnan, Peoples R China
4.Southwest Forestry Univ, Key Lab Forest Resources Conservat & Utilisat Sou, Minist Educ, Kunming, Yunnan, Peoples R China
Recommended Citation
GB/T 7714
Deng, Guogang,Zhou, Bei,Wang, Jing,et al. Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2019,168:232-252.
APA Deng, Guogang.,Zhou, Bei.,Wang, Jing.,Chen, Zhuo.,Gong, Liang.,...&Yang, Xiaodong.(2019).Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,168,232-252.
MLA Deng, Guogang,et al."Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 168(2019):232-252.
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