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Synthesis, Structure Elucidation and H + /K + ‐ATPase Inhibitory Activity of Bisabolangelone Reduction Derivatives
Author(s) -
Huang Nianyu,
Chen Lei,
Liao Zhaojiang,
Fang Hubiao,
Wang Junzhi,
Zou Kun
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201100051
Subject(s) - chemistry , stereochemistry , crystal structure , ring (chemistry) , proton nmr , atpase , inhibitory postsynaptic potential , medicinal chemistry , crystallography , enzyme , organic chemistry , neuroscience , biology
Nine bisabolangelone reduction derivatives were synthesized and separated as potential anti‐ulcer agent. Their structures were characterized by 2D NMR, IR, ESI‐MS, elemental analysis and single‐crystal X‐ray diffraction analysis. Preliminarily H + /K + ‐ATPase activity evaluation indicated that all the target compounds had a certain inhibitory effect, and compounds II and IV exhibited the better inhibitory activity against H + /K + ‐ATPase than bisabolangelone and the commercial omeprazole with the IC 50 of 23.21 and 65.32 μmol/L, respectively. The initial structure‐activity analysis suggested that the presence of carbonyl group in six‐membered ring and double bond in side‐chain seemed to be necessary to the activity.