Literature DB >> 16380254

Synthesis and biological evaluation of 5-[(aryl)(1H-imidazol-1-yl)methyl]-1H-indoles: potent and selective aromatase inhibitors.

Marie-Pierre Lézé1, Marc Le Borgne, Patricia Pinson, Anja Palusczak, Muriel Duflos, Guillaume Le Baut, Rolf W Hartmann.   

Abstract

The synthesis and the aromatase (CYP19) inhibitory activity of 5-[(aryl)(imidazol-1-yl)methyl]-1H-indoles were reported. Among the tested racemate compounds, 5-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole 8b emerged as a potent CYP19 inhibitor (IC(50)=15.3 nM). Chiral chromatography allowed isolation of the (+) enantiomer 8b2, which was about twice as active as the racemate (IC(50)=9 nM).

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Year:  2005        PMID： 16380254     DOI： 10.1016/j.bmcl.2005.11.099

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  7 in total

1.  Development of a new class of aromatase inhibitors: design, synthesis and inhibitory activity of 3-phenylchroman-4-one (isoflavanone) derivatives.

Authors:  Kevin Bonfield; Erica Amato; Tony Bankemper; Hannah Agard; Jeffrey Steller; James M Keeler; David Roy; Adam McCallum; Stefan Paula; Lili Ma
Journal:  Bioorg Med Chem       Date:  2012-02-27       Impact factor: 3.641

2.  Docking and 3D-QSAR studies of diverse classes of human aromatase (CYP19) inhibitors.

Authors:  Partha Pratim Roy; Kunal Roy
Journal:  J Mol Model       Date:  2010-03-01       Impact factor: 1.810

3.  Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1.

Authors:  Allan M Prior; Xufen Yu; Eun-Jung Park; Tamara P Kondratyuk; Yan Lin; John M Pezzuto; Dianqing Sun
Journal:  Bioorg Med Chem Lett       Date:  2017-11-06       Impact factor: 2.823

4.  2-[(1H-Imidazol-1-yl)meth-yl]-1-[4-(trifluoro-meth-yl)phen-yl]-1H-indole.

Authors:  Rui Wang; Hong-Fan Shi; Lin Du; Jing-Feng Zhao; Jian-Ping Liu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-17

5.  3-Pyridyl substituted aliphatic cycles as CYP11B2 inhibitors: aromaticity abolishment of the core significantly increased selectivity over CYP1A2.

Authors:  Lina Yin; Qingzhong Hu; Rolf W Hartmann
Journal:  PLoS One       Date:  2012-11-01       Impact factor: 3.240

6.  Synthesis and biological evaluation of thieno[3,2-d]- pyrimidinones, thieno[3,2-d]pyrimidines and quinazolinones: conformationally restricted 17b-hydroxysteroid dehydrogenase type 2 (17b-HSD2) inhibitors.

Authors:  Enrico Perspicace; Sandrine Marchais-Oberwinkler; Rolf W Hartmann
Journal:  Molecules       Date:  2013-04-16       Impact factor: 4.411

7.  Synthesis, Optimization, Antifungal Activity, Selectivity, and CYP51 Binding of New 2-Aryl-3-azolyl-1-indolyl-propan-2-ols.

Authors:  Nicolas Lebouvier; Fabrice Pagniez; Young Min Na; Da Shi; Patricia Pinson; Mathieu Marchivie; Jean Guillon; Tarek Hakki; Rita Bernhardt; Sook Wah Yee; Claire Simons; Marie-Pierre Lézé; Rolf W Hartmann; Angélique Mularoni; Guillaume Le Baut; Isabelle Krimm; Ruben Abagyan; Patrice Le Pape; Marc Le Borgne
Journal:  Pharmaceuticals (Basel)       Date:  2020-08-08
  7 in total

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