title: Synthesis and cytotoxic evaluation of 1-carboxamide and 1-amino side chain substituted β-carbolines.
abstract: The condensation of alkylenediamine with ethyl β-carboline-1-carboxylate and 1-bromo-β-carboline gave β-carboline-1-carboxamides and 1-amino-β-carbolines, respectively. Some of these β-carbolines were active against a panel of human tumor cell lines, and 1-amino derivatives were more potent than their 1-carboxamide congeners. In particular, among the 1-amino-β-carbolines, the N(9)-arylated alkyl substituted β-carbolines exhibited the most interesting cytotoxic activities with IC(50) value of lower than 20 μM. The preliminary structure-activity relationships (SARs) analysis suggested that (1) 1-amino substituents were the advisable pharmacophoric group for enhanced cytotoxic activities; (2) the introduction of appropriate arylated alkyl groups into position-9 of β-carboline facilitated their cytotoxic potencies.
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-sen University, 135 Xin Gang West Road, Guangzhou 510275, PR China.
authors.forename: Chunming
authors.initials: C
authors.lastname: Ma
authors.forename: Rihui
authors.initials: R
authors.lastname: Cao
authors.forename: Buxi
authors.initials: B
authors.lastname: Shi
authors.forename: Xiantai
authors.initials: X
authors.lastname: Zhou
authors.forename: Qin
authors.initials: Q
authors.lastname: Ma
authors.forename: Jie
authors.initials: J
authors.lastname: Sun
authors.forename: Liang
authors.initials: L
authors.lastname: Guo
authors.forename: Wei
authors.initials: W
authors.lastname: Yi
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Chen
authors.forename: Huacan
authors.initials: H
authors.lastname: Song
mesh_terms: D000577:Amides / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D002243:Carbolines