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Synthesis of Novel 3‐ N ‐substituted Carbazole Derivatives and Evaluation of their Abilities to Inhibit Platelet Aggregation
Author(s) -
Kim Jiseon,
Jung SangHyuk,
Yun Eunju,
Cho SooHyun,
Yuseok O,
Kim JiEun,
Kim YoungHo,
Myung ChangSeon,
Song GyuYong
Publication year - 2018
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11462
Subject(s) - moiety , carbazole , chemistry , nitro , stereochemistry , urea , in vitro , platelet aggregation , carbamate , amine gas treating , combinatorial chemistry , platelet , biochemistry , organic chemistry , alkyl , immunology , biology
The carbazole moiety exhibits various biological activities, including anticancer, antiviral, anti‐inflammatory, and antimicrobial activities; some compounds containing the moiety also inhibit platelet aggregation. In the present study, we synthesized a series of 3‐ N ‐substituted carbazole derivatives and evaluated their abilities to inhibit in vitro platelet aggregation induced by collagen (5 μg/mL). Of the synthesized compounds, compound 5q (JSCa15), with a urea linkage within the carbazole framework, exhibited the strongest inhibitory activity (98.25% at 30 μM). Interestingly, reduction of the nitro group of compound 5q to an amine exhibited significantly decreased activity (compound 5r , 5.18% at 30 μM). Also, substitution of the urea moiety of compound 5q with a carbamate moiety resulted in a considerable loss of activity (compound 8a , 5.91% at 30 μM). These results suggest that the urea moieties and nitro groups of 3‐ N ‐substituted carbazole derivatives may play key roles in inhibiting in vitro platelet aggregation induced by collagen.