title: Synthesis and cytotoxic activity of novel hexahydropyrrolo[2,3-b]indole imidazolium salts.
abstract: A series of novel hexahydropyrrolo[2,3-b]indole-1H-imidazolium salts were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the 5,6-dimethyl-benzimidazole ring, and substitution of the imidazolyl-3-position with a 2-bromobenzyl or 2-naphthylmethyl group, were important for the cytotoxic activity. Notably, Compound 43, bearing a 2-bromobenzyl substituent at position-3 of 5,6-dimethyl-benzimidazole, was found to possess the most potent derivative against five human tumor cell lines with IC50 values below 2.68μM and more selective towards SMMC-7721, A549 and SW480 cell lines. Compounds 25 and 39 were more selective to HL-60 and MCF-7 cell lines with IC50 values of 0.47 and 1.46μM.
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Yunjing
authors.initials: Y
authors.lastname: Zhou
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Kunyun
authors.initials: K
authors.lastname: Duan
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Liang
authors.initials: L
authors.lastname: Zhu
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Zhengfeng
authors.initials: Z
authors.lastname: Liu
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Chaobo
authors.initials: C
authors.lastname: Zhang
authors.affiliation: School of Chemistry & Environment, Engineering Research Center of Biopolymer Functional Materials of Yunnan, Yunnan Minzu University, Kunming 650500, PR China.
authors.forename: Lijuan
authors.initials: L
authors.lastname: Yang
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Minyan
authors.initials: M
authors.lastname: Li
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China. Electronic address: zhanghbyd@gmail.com.
authors.forename: Hongbin
authors.initials: H
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China. Electronic address: xdyang@ynu.edu.cn.
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Yang
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000494:pharmacology; D001969:Bromobenzenes / Q000138:chemical synthesis / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis / Q000494:pharmacology*; D007211:Indoles / Q000138:chemical synthesis / Q000494:pharmacology*; D009281:Naphthalenes / Q000138:chemical synthesis / Q000494:pharmacology; D011758:Pyrroles / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001562:Benzimidazoles; D001969:Bromobenzenes; D007093:Imidazoles; D007211:Indoles; D009281:Naphthalenes; D011758:Pyrroles
keywords: Hexahydropyrrolo[2,3-b]indole; Imidazolium salts; Structure–activity relationships