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Synthesis and biological activities of novel chiral fluorinated β‐carboline derivatives
Author(s) -
Ding Jin Chang,
Huang Xiao Bo,
Wu Hua Yue,
Chen Jie Zhi,
Cai Ming Tiao,
Liu Miao Chang
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450635
Subject(s) - chemistry , enantiomer , monoamine oxidase , trifluoromethyl , stereochemistry , inhibitory postsynaptic potential , in vitro , carboxamide , biochemistry , organic chemistry , enzyme , alkyl , neuroscience , biology
A series of unreported chiral β‐carbolines 4 with trifluoromethyl group at position‐1 and chiral carboxamide chains or amino acid ester chains at position‐3 has been designed and synthesized. The results of bioassay in vitro show that compounds 4e, 4i and 4k show 78.8%, 84.0% and 78.9% inhibition on monoamine oxidase, in 1 mmol/L, respectively, and compound 4e also exhibit 60.9% inhibitory activity on tumor lung cell A‐549 in 10 −5 mmol/L. In view of different configuration, the inhibitory activity on monoamine oxidase of S ‐enantiomer of the target compound is better than that of R ‐enantiomer.