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Vol. 26 No. 8 (2014): Vol 26 Issue 8

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Syntheses and QSAR Studies of Benzylimidazole Derivatives and Benzylcarbazole as Potential Aromatase Inhibitors

https://doi.org/10.14233/ajchem.2014.16016
Y. Dai
Key Laboratory of Industrial Fermentation Microbiology (Tianjin University of Science & Technology), Ministry of Education, College of Bioengineering, Tianjin University of Science and Technology, Tianjin 300457, P.R. China
Y. Xiao
Key Laboratory of Industrial Fermentation Microbiology (Tianjin University of Science & Technology), Ministry of Education, College of Bioengineering, Tianjin University of Science and Technology, Tianjin 300457, P.R. China
Q. Wang
Key Laboratory of Industrial Fermentation Microbiology (Tianjin University of Science & Technology), Ministry of Education, College of Bioengineering, Tianjin University of Science and Technology, Tianjin 300457, P.R. China
S. Wei
Key Laboratory of Industrial Fermentation Microbiology (Tianjin University of Science & Technology), Ministry of Education, College of Bioengineering, Tianjin University of Science and Technology, Tianjin 300457, P.R. China
X. Zhang
Key Laboratory of Industrial Fermentation Microbiology (Tianjin University of Science & Technology), Ministry of Education, College of Bioengineering, Tianjin University of Science and Technology, Tianjin 300457, P.R. China
Z. Ma
Department of Ocean Science and Engineering, Zhejiang University, Hangzhou 310058, P.R. China
H. Zheng
School of Life Science and Technology, China Pharmaceutical University, Nanjing 210009, P.R. China
M. Hou
Key Laboratory of Industrial Fermentation Microbiology (Tianjin University of Science & Technology), Ministry of Education, College of Bioengineering, Tianjin University of Science and Technology, Tianjin 300457, P.R. China
T. Zhang
Key Laboratory of Industrial Fermentation Microbiology (Tianjin University of Science & Technology), Ministry of Education, College of Bioengineering, Tianjin University of Science and Technology, Tianjin 300457, P.R. China

Corresponding Author(s) : Y. Dai

yjdai@126.com

Asian Journal of Chemistry, Vol. 26 No. 8 (2014): Vol 26 Issue 8

Abstract

In this study, in order to explore new structures and chemical entities as aromatase inhibitors, benzylcarbazole, 12 benzylimidazole derivatives with different substituents on both phenyl and imidazole rings were synthesized and their aromatase inhibitory were evaluated with fluorescent substrate detection method. The results showed that the compounds with carboxyl and ester groups in phenyl ring show better inhibitory activity. The introduction of alkyl groups in imidazole may improve the aromatase inhibitory activity. Most of the compounds were more potent than aminoglutethimide and tamoxifen. 2-[2-{(2-ethyl-4-methyl-1H-imidazol-1-yl)methyl}phenyl]acetic acid and benzylcarbazole have the highest bioactivities with IC50 values of 6.19 μM and 2.72 μM respectively. A meaningful QSAR model with LOF = 0.00359, R2 = 0.9914, Adj-R2 = 0.9853, R2cv = 0.9639, F = 161.8, was constructed with genetic functional algorithm using discovery studio 2.1 package.

Keywords

Benzylimidazole Benzylcarbazole Aromatase inhibitors QSAR
Dai, Y., Xiao, Y., Wang, Q., Wei, S., Zhang, X., Ma, Z., … Zhang, T. (2014). Syntheses and QSAR Studies of Benzylimidazole Derivatives and Benzylcarbazole as Potential Aromatase Inhibitors. Asian Journal of Chemistry, 26(8), 2381–2388. https://doi.org/10.14233/ajchem.2014.16016
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