Synthesis of New Flavanone Derivatives of Farrerol and Preliminary SAR Studies on Anti-VSMCs Vegetation Activity

Chemical Research in Chinese Universities ›› 2011, Vol. 27 ›› Issue (2): 237-240.

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Synthesis of New Flavanone Derivatives of Farrerol and Preliminary SAR Studies on Anti-VSMCs Vegetation Activity

SHI Lei¹, FENG Xiu-e¹, LIN Wen-han², FANG Lian-hua³, DU Guan-hua³ and LI Qing-shan^1,2*

1. School of Pharmaceutical Science, Shanxi Medical University, Taiyuan 030001, P. R. China;
2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, P. R. China;
3. Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. China

Received:2010-01-29 Revised:2010-04-22 Online:2011-03-25 Published:2011-03-09
Contact: LI Qing-shan E-mail:qingshanl@yahoo.com
Supported by:
Supported by the National High-Tech Research and Development Program of China(No.2006AA09Z446), the Fund of State Key Laboratory of Natural and Biomimetic Drags, Peking University, China(No.20080210), the Shanxi Provincial Foundation for Overseas Returned, China(No.2009021005), the Program for the Top Young and Middle-aged Innovative Talents of Higher Learning In- stitutions of Shanxi Province, China(No.20091041-1) and the Innovative Program of Shanxi Medical University, China (No.38).

Abstract

Abstract: A series of new flavanone derivatives of farrerol was designed and synthesized as a potent inhibitor of vascular smooth muscle cells(VSMCs) vegetation according to a convenient method. The structures of all the synthesized compounds were confirmed by 1H NMR, 13C NMR and EIHR-MS. The biological activities of these compounds against VSMCs in vitro were evaluated. The assay results indicate that two compounds, 5,7-dihydroxy-6,8-dimethyl- 2-(2-nitrophenyl)chroman-4-one(7f) and 2,3-dibromo-4,5-dihydroxydiphenylmethanone(7j) exhibited high activity against VSMCs in vitro with IC50 values of 9.9 and 6.7 μmol/L, respectively, and the preliminary structure-activity relationship(SAR) was described.

Key words: Synthesis, Flavanone derivative, Anti-VSMCs vegetation

SHI Lei, FENG Xiu-e, LIN Wen-han, FANG Lian-hua, DU Guan-hua and LI Qing-shan*. Synthesis of New Flavanone Derivatives of Farrerol and Preliminary SAR Studies on Anti-VSMCs Vegetation Activity[J]. Chemical Research in Chinese Universities, 2011, 27(2): 237-240.

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Synthesis of New Flavanone Derivatives of Farrerol and Preliminary SAR Studies on Anti-VSMCs Vegetation Activity

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