Literature DB >> 24900439

Synthesis and biological evaluation of cyclic sulfamide derivatives as 11β-hydroxysteroid dehydrogenase 1 inhibitors.

Se Hoan Kim1, Ju Han Bok2, Jae Hong Lee1, Il Hyang Kim1, Sung Wook Kwon1, Gui Bin Lee2, Seung Kyu Kang2, Ji Seon Park2, Won Hoon Jung2, Hee Yeon Kim2, Sang Dal Rhee2, Sung Hoon Ahn2, Myung Ae Bae2, Deok Chan Ha3, Ki Young Kim2, Jin Hee Ahn2.   

Abstract

A new series of cyclic sulfamide derivatives were synthesized and evaluated for their ability to inhibit 11β-HSD1. Among this series, 18e showed good in vitro activity toward human 11β-HSD1, selectivity against 11β-HSD2, microsomal stability, and pharmacokinetic and safety profiles (hERG, CYP, and acute toxicity). Additionally, 18e exhibited good in vivo efficacy in rat and monkey models.

Entities:  

Keywords:  11β-hydroxysteroid dehydrogenase type 1; adamantyl group; antidiabetic agents; cyclic sulfamide; diabetes

Year:  2012        PMID： 24900439      PMCID： PMC4025780          DOI： 10.1021/ml200226x

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  15 in total

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2.  The development and SAR of pyrrolidine carboxamide 11beta-HSD1 inhibitors.

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3.  Synthesis and optimization of novel 4,4-disubstituted cyclohexylbenzamide derivatives as potent 11β-HSD1 inhibitors.

Authors:  Daqing Sun; Zhulun Wang; Seb Caille; Michael DeGraffenreid; Felix Gonzalez-Lopez de Turiso; Randall Hungate; Juan C Jaen; Ben Jiang; Lisa D Julian; Ron Kelly; Dustin L McMinn; Jacob Kaizerman; Yosup Rew; Athena Sudom; Hua Tu; Stefania Ursu; Nigel Walker; Maren Willcockson; Xuelei Yan; Qiuping Ye; Jay P Powers
Journal:  Bioorg Med Chem Lett       Date:  2010-10-31       Impact factor: 2.823

4.  Discovery of adamantane ethers as inhibitors of 11beta-HSD-1: Synthesis and biological evaluation.

Authors:  Jyoti R Patel; Qi Shuai; Jurgen Dinges; Marty Winn; Marina Pliushchev; Steven Fung; Katina Monzon; William Chiou; Jiahong Wang; Liping Pan; Seble Wagaw; Kenneth Engstrom; Francis A Kerdesky; Kenton Longenecker; Russell Judge; Wenying Qin; Hovis M Imade; Deanne Stolarik; David W A Beno; Michael Brune; Linda E Chovan; Hing L Sham; Peer Jacobson; J T Link
Journal:  Bioorg Med Chem Lett       Date:  2006-10-28       Impact factor: 2.823

5.  Bicyclo[2.2.2]octyltriazole inhibitors of 11β-hydoxysteroid dehydrogenase type 1. Pharmacological agents for the treatment of metabolic syndrome.

Authors:  Milana Maletic; Aaron Leeman; Michael Szymonifka; Steven S Mundt; Hratch J Zokian; Kashmira Shah; Jasminka Dragovic; Kathy Lyons; Rolf Thieringer; Anne H Vosatka; James Balkovec; Sherman T Waddell
Journal:  Bioorg Med Chem Lett       Date:  2011-01-11       Impact factor: 2.823

Review 6.  11beta-hydroxysteroid dehydrogenase type 1 inhibitors as promising therapeutic drugs for diabetes: status and development.

Authors:  R Ge; Y Huang; G Liang; X Li
Journal:  Curr Med Chem       Date:  2010       Impact factor: 4.530

7.  The 11-beta-hydroxysteroid dehydrogenase type 1 inhibitor INCB13739 improves hyperglycemia in patients with type 2 diabetes inadequately controlled by metformin monotherapy.

Authors:  Julio Rosenstock; Salomon Banarer; Vivian A Fonseca; Silvio E Inzucchi; William Sun; Wenqing Yao; Gregory Hollis; Robert Flores; Richard Levy; William V Williams; Jonathan R Seckl; Reid Huber
Journal:  Diabetes Care       Date:  2010-04-22       Impact factor: 17.152

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

9.  Discovery and structure-activity relationships of pentanedioic acid diamides as potent inhibitors of 11beta-hydroxysteroid dehydrogenase type I.

Authors:  Didier Roche; Denis Carniato; Caroline Leriche; Franck Lepifre; Serge Christmann-Franck; Ulrich Graedler; Christine Charon; Sophie Bozec; Liliane Doare; Fabien Schmidlin; Marc Lecomte; Eric Valeur
Journal:  Bioorg Med Chem Lett       Date:  2009-04-01       Impact factor: 2.823

10.  Spirocyclic ureas: orally bioavailable 11 beta-HSD1 inhibitors identified by computer-aided drug design.

Authors:  Colin M Tice; Wei Zhao; Zhenrong Xu; Salvacion T Cacatian; Robert D Simpson; Yuan-Jie Ye; Suresh B Singh; Brian M McKeever; Peter Lindblom; Joan Guo; Paula M Krosky; Barbara A Kruk; Jennifer Berbaum; Richard K Harrison; Judith J Johnson; Yuri Bukhtiyarov; Reshma Panemangalore; Boyd B Scott; Yi Zhao; Joseph G Bruno; Linghang Zhuang; Gerard M McGeehan; Wei He; David A Claremon
Journal:  Bioorg Med Chem Lett       Date:  2010-01-04       Impact factor: 2.823
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  4 in total

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2.  Discovery of 2-Alkyl-1-arylsulfonylprolinamides as 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors.

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Journal:  ACS Med Chem Lett       Date:  2012-09-20       Impact factor: 4.345

3.  Synthesis and Selective Functionalization of Thiadiazine 1,1-Dioxides with Efficacy in a Model of Huntington's Disease.

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Journal:  ACS Med Chem Lett       Date:  2020-02-20       Impact factor: 4.345

4.  Stereocontrolled synthesis of bicyclic ureas and sulfamides via Pd-catalyzed alkene carboamination reactions.

Authors:  Nicholas R Babij; Jordan R Boothe; Grace M McKenna; Ryan M Fornwald; John P Wolfe
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  4 in total

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