Citation: Jung Jong-Woon, Damodar Kongara, Kim Jin-Kyung, Jun Jong-Gab. First synthesis and in vitro biological assessment of isosideroxylin, 6, 8-dimethylgenistein and their analogues as nitric oxide production inhibition agents[J]. Chinese Chemical Letters, ;2017, 28(5): 1114-1118. doi: 10.1016/j.cclet.2016.12.041 shu

First synthesis and in vitro biological assessment of isosideroxylin, 6, 8-dimethylgenistein and their analogues as nitric oxide production inhibition agents

a.
Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon 24252, South Korea
b.
Department of Biomedical Science, College of Natural Science, Catholic University of Daegu, Gyeungsan-Si 38430, South Korea

Corresponding author: Jun Jong-Gab, jgjun@hallym.ac.kr
Received Date: 31 October 2016
Revised Date: 6 December 2016
Accepted Date: 14 December 2016
Available Online: 8 May 2017

Figures(4)

A modular and efficient synthesis of the biologically significant C-methylisoflavones isosideroxylin (1), 6, 8-dimethylgenistein (2) and their analogues (3-8) is established for the first time. The synthesis is realized in 7-8 steps in overall yields of 16%-24% from commercially inexpensive phloroglucinol and features a high yielding Vilsmeier-Haack reaction, Friedel-Crafts acylation, Gammill's protocol and Suzuki coupling as the pivotal transformations. Next, these compounds evaluated for their inhibitory potency on the production of nitric oxide (NO) in lipopolysaccharide (LPS)-activated RAW-264.7 cells as an indicator of anti-inflammatory activity. The results showed that all the compounds decreased NO production in a dose-dependent manner without marked cytotoxicity and IC₅₀ values are found in the range of 10.17-33.88 μmol/L. Of note, compounds 3 followed by 1, 7 and 8 show comparable inhibitory activity with positive control (N-monomethyl-_L-arginine, L-NMMA).
- Isosideroxylin,
- 6, 8-Dimethylgenistein,
- Vilsmeier-Haack reaction,
- Suzuki coupling,
- Nitric oxide (NO),
- Anti-inflammatory
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