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Literature DB >> 18440812

Phenylcyclobutyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.

Yuping Zhu¹, Steven H Olson, Donald Graham, Gool Patel, Anne Hermanowski-Vosatka, Steven Mundt, Kashmira Shah, Marty Springer, Rolf Thieringer, Samuel Wright, Jianying Xiao, Hratch Zokian, Jasminka Dragovic, James M Balkovec.

Abstract

3-(Phenylcyclobutyl)-1,2,4-triazoles were identified as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1). These were active both in vitro and in an in vivo mouse pharmacodynamic (PD) model. Fluorine substitution of the cyclobutane ring improved the pharmacokinetic profile significantly. The synthesis and structure-activity relationships are presented.

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Year: 2008 PMID： 18440812 DOI： 10.1016/j.bmcl.2008.04.014

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

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Cited

8 in total

Review 1. Crystal structures of 11β-hydroxysteroid dehydrogenase type 1 and their use in drug discovery.

Authors: Mark P Thomas; Barry V L Potter
Journal: Future Med Chem Date: 2011-03 Impact factor: 3.808

Review 2. Greener organic synthetic methods: Sonochemistry and heterogeneous catalysis promoted multicomponent reactions.

Authors: Ingrid V Machado; Jhonathan R N Dos Santos; Marcelo A P Januario; Arlene G Corrêa
Journal: Ultrason Sonochem Date: 2021-08-05 Impact factor: 7.491

3. Pharmacokinetic-pharmacodynamic studies of the 11β-hydroxysteroid dehydrogenase type 1 inhibitor MK-0916 in healthy subjects.

Authors: D Hamish Wright; Julie A Stone; Tami M Crumley; Larissa Wenning; Wei Zheng; Kerri Yan; Amy Yifan Yang; Li Sun; Caroline Cilissen; Steven Ramael; Anne Hermanowski-Vosatka; Ronald B Langdon; Keith M Gottesdiener; John A Wagner; Eseng Lai
Journal: Br J Clin Pharmacol Date: 2013-12 Impact factor: 4.335

4. Optimization of 1,2,4-Triazolopyridines as Inhibitors of Human 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD-1).

Authors: Jun Li; Lawrence J Kennedy; Haixia Wang; James J Li; Steven J Walker; Zhenqiu Hong; Stephen P O'Connor; Akbar Nayeem; Daniel M Camac; Paul E Morin; Steven Sheriff; Mengmeng Wang; Timothy Harper; Rajasree Golla; Ramakrishna Seethala; Thomas Harrity; Randolph P Ponticiello; Nathan N Morgan; Joseph R Taylor; Rachel Zebo; David A Gordon; Jeffrey A Robl
Journal: ACS Med Chem Lett Date: 2014-05-22 Impact factor: 4.345

8. Crystal structure, Hirshfeld surface analysis and DFT studies of 5-(adamantan-1-yl)-3-[(4-chlorobenzyl)sulfanyl]-4-methyl-4H-1,2,4-triazole, a potential 11β-HSD1 inhibitor.

Authors: Lamya H Al-Wahaibi; Jacques Joubert; Olivier Blacque; Nora H Al-Shaalan; Ali A El-Emam
Journal: Sci Rep Date: 2019-12-24 Impact factor: 4.379

8 in total

Phenylcyclobutyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.

Review 1. Crystal structures of 11β-hydroxysteroid dehydrogenase type 1 and their use in drug discovery.

Review 2. Greener organic synthetic methods: Sonochemistry and heterogeneous catalysis promoted multicomponent reactions.

3. Pharmacokinetic-pharmacodynamic studies of the 11β-hydroxysteroid dehydrogenase type 1 inhibitor MK-0916 in healthy subjects.

4. Optimization of 1,2,4-Triazolopyridines as Inhibitors of Human 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD-1).

Review 5. 11β-hydroxysteroid dehydrogenases and the brain: from zero to hero, a decade of progress.

6. Discovery of adamantyl heterocyclic ketones as potent 11β-hydroxysteroid dehydrogenase type 1 inhibitors.

7. Synthesis, Stability, and Biological Studies of Fluorinated Analogues of Thromboxane A₂.

8. Crystal structure, Hirshfeld surface analysis and DFT studies of 5-(adamantan-1-yl)-3-[(4-chlorobenzyl)sulfanyl]-4-methyl-4H-1,2,4-triazole, a potential 11β-HSD1 inhibitor.

Phenylcyclobutyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.

Review 1. Crystal structures of 11β-hydroxysteroid dehydrogenase type 1 and their use in drug discovery.

Review 2. Greener organic synthetic methods: Sonochemistry and heterogeneous catalysis promoted multicomponent reactions.

3. Pharmacokinetic-pharmacodynamic studies of the 11β-hydroxysteroid dehydrogenase type 1 inhibitor MK-0916 in healthy subjects.

4. Optimization of 1,2,4-Triazolopyridines as Inhibitors of Human 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD-1).

Review 5. 11β-hydroxysteroid dehydrogenases and the brain: from zero to hero, a decade of progress.

6. Discovery of adamantyl heterocyclic ketones as potent 11β-hydroxysteroid dehydrogenase type 1 inhibitors.

7. Synthesis, Stability, and Biological Studies of Fluorinated Analogues of Thromboxane A2.

8. Crystal structure, Hirshfeld surface analysis and DFT studies of 5-(adamantan-1-yl)-3-[(4-chlorobenzyl)sulfanyl]-4-methyl-4H-1,2,4-triazole, a potential 11β-HSD1 inhibitor.

7. Synthesis, Stability, and Biological Studies of Fluorinated Analogues of Thromboxane A₂.