Literature DB >> 19701236

Derivatives of (phenylsulfonamido-methyl)nicotine and (phenylsulfonamido-methyl)thiazole as novel 11beta-hydroxysteroid dehydrogenase type 1 inhibitors: synthesis and biological activities in vitro.

Xu Zhang1, Yang Zhou, Yu Shen, Li-li Du, Jun-hua Chen, Ying Leng, Jian-hua Shen.   

Abstract

AIM: To design and synthese a novel class of 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) inhibitors, featuring the (phenylsulfonamido-methyl)pyridine and (phenylsulfonamido-methyl)thiazole framework.
METHODS: Our initial lead 4-(phenylsulfonamido-methyl)benzamides were modified. Inhibition of human and mouse 11beta-HSD1 enzymatic activities by the new compounds was determined by a scintillation proximity assay (SPA) using microsomes containing 11beta-HSD1.
RESULTS: Sixteen new compounds (6a-6h, 7a-7h) were designed, synthesized and bioassayed. In dose-response studies, several compounds showed strong inhibitory activities with IC50 values at nanomolar or low nanomolar concentrations. Structure-activity relationships are also discussed with respect to molecular docking results.
CONCLUSION: This study provides two promising new templates for 11beta-HSD1 inhibitors.

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Year:  2009        PMID: 19701236      PMCID: PMC4007184          DOI: 10.1038/aps.2009.118

Source DB:  PubMed          Journal:  Acta Pharmacol Sin        ISSN: 1671-4083            Impact factor:   6.150


  12 in total

1.  Development and application of a scintillation proximity assay (SPA) for identification of selective inhibitors of 11beta-hydroxysteroid dehydrogenase type 1.

Authors:  S Mundt; K Solly; R Thieringer; A Hermanowski-Vosatka
Journal:  Assay Drug Dev Technol       Date:  2005-08       Impact factor: 1.738

2.  Structure-based virtual screening for identification of novel 11beta-HSD1 inhibitors.

Authors:  Huaiyu Yang; Yu Shen; Junhua Chen; Qunfeng Jiang; Ying Leng; Jianhua Shen
Journal:  Eur J Med Chem       Date:  2008-06-20       Impact factor: 6.514

3.  Blockade of glucocorticoid excess at the tissue level: inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 as a therapy for type 2 diabetes.

Authors:  Christopher Fotsch; Minghan Wang
Journal:  J Med Chem       Date:  2008-07-22       Impact factor: 7.446

4.  A transgenic model of visceral obesity and the metabolic syndrome.

Authors:  H Masuzaki; J Paterson; H Shinyama; N M Morton; J J Mullins; J R Seckl; J S Flier
Journal:  Science       Date:  2001-12-07       Impact factor: 47.728

5.  Differentiation of adipose stromal cells: the roles of glucocorticoids and 11beta-hydroxysteroid dehydrogenase.

Authors:  I J Bujalska; S Kumar; M Hewison; P M Stewart
Journal:  Endocrinology       Date:  1999-07       Impact factor: 4.736

Review 6.  Regulation of phosphoenolpyruvate carboxykinase (GTP) gene expression.

Authors:  R W Hanson; L Reshef
Journal:  Annu Rev Biochem       Date:  1997       Impact factor: 23.643

Review 7.  11beta-Hydroxysteroid dehydrogenase Type 1 in obesity and Type 2 diabetes.

Authors:  T M Stulnig; W Waldhäusl
Journal:  Diabetologia       Date:  2003-12-03       Impact factor: 10.122

8.  Metabolic syndrome without obesity: Hepatic overexpression of 11beta-hydroxysteroid dehydrogenase type 1 in transgenic mice.

Authors:  Janice M Paterson; Nicholas M Morton; Catherine Fievet; Christopher J Kenyon; Megan C Holmes; Bart Staels; Jonathan R Seckl; John J Mullins
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-26       Impact factor: 11.205

Review 9.  11beta-hydroxysteroid dehydrogenase type 1: a tissue-specific regulator of glucocorticoid response.

Authors:  Jeremy W Tomlinson; Elizabeth A Walker; Iwona J Bujalska; Nicole Draper; Gareth G Lavery; Mark S Cooper; Martin Hewison; Paul M Stewart
Journal:  Endocr Rev       Date:  2004-10       Impact factor: 19.871

Review 10.  Diabetes mellitus: pathogenesis and treatment strategies.

Authors:  Jay S Skyler
Journal:  J Med Chem       Date:  2004-08-12       Impact factor: 7.446

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  1 in total

Review 1.  Human hydroxysteroid dehydrogenases and pre-receptor regulation: insights into inhibitor design and evaluation.

Authors:  Trevor M Penning
Journal:  J Steroid Biochem Mol Biol       Date:  2011-01-25       Impact factor: 4.292

  1 in total

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