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

Cheng H, Hoffman J, Le P, Nair SK, Cripps S, Matthews J, Smith C, Yang M, Kupchinsky S, Dress K, Edwards M, Cole B, Walters E, Loh C, Ermolieff J, Fanjul A, Bhat GB, Herrera J, Pauly T, Hosea N, Paderes G, Rejto P
Bioorg Med Chem Lett 20 2897-902 (2010)
Cited: 19 times
EuropePMC logo PMID: 20363126

Abstract

The design and development of a series of highly selective pyrrolidine carboxamide 11beta-HSD1 inhibitors are described. These compounds including PF-877423 demonstrated potent in vitro activity against both human and mouse 11beta-HSD1 enzymes. In an in vivo assay, PF-877423 inhibited the conversion of cortisone to cortisol. Structure guided optimization effort yielded potent and stable 11beta-HSD1 selective inhibitor 42.

Reviews - 3lz6 mentioned but not cited (1)

  1. Crystal structures of 11β-hydroxysteroid dehydrogenase type 1 and their use in drug discovery. Thomas MP, Potter BV. Future Med Chem 3 367-390 (2011)

Articles - 3lz6 mentioned but not cited (2)

  1. Impaired oxidoreduction by 11β-hydroxysteroid dehydrogenase 1 results in the accumulation of 7-oxolithocholic acid. Penno CA, Morgan SA, Vuorinen A, Schuster D, Lavery GG, Odermatt A. J. Lipid Res. 54 2874-2883 (2013)
  2. Protein Targets of Frankincense: A Reverse Docking Analysis of Terpenoids from Boswellia Oleo-Gum Resins. Byler KG, Setzer WN. Medicines (Basel) 5 (2018)


Articles citing this publication (16)

  1. Discovery of SAR184841, a potent and long-lasting inhibitor of 11β-hydroxysteroid dehydrogenase type 1, active in a physiopathological animal model of T2D. Venier O, Pascal C, Braun A, Namane C, Mougenot P, Crespin O, Pacquet F, Mougenot C, Monseau C, Onofri B, Dadji-Faïhun R, Leger C, Ben-Hassine M, Van-Pham T, Ragot JL, Philippo C, Farjot G, Noah L, Maniani K, Boutarfa A, Nicolaï E, Guillot E, Pruniaux MP, Güssregen S, Engel C, Coutant AL, de Miguel B, Castro A. Bioorg. Med. Chem. Lett. 23 2414-2421 (2013)
  2. 1,1-Dioxo-5,6-dihydro-[4,1,2]oxathiazines, a novel class of 11ß-HSD1 inhibitors for the treatment of diabetes. Böhme T, Engel CK, Farjot G, Güssregen S, Haack T, Tschank G, Ritter K. Bioorg. Med. Chem. Lett. 23 4685-4691 (2013)
  3. Synthesis and 11β hydroxysteroid dehydrogenase 1 inhibition of thiazolidine derivatives with an adamantyl group. Kwon SW, Kang SK, Lee JH, Bok JH, Kim CH, Dal Rhee S, Jung WH, Kim HY, Bae MA, Song JS, Ha DC, Cheon HG, Kim KY, Ahn JH. Bioorg. Med. Chem. Lett. 21 435-439 (2011)
  4. Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives. Al-Abdullah ES, Al-Tuwaijri HM, Hassan HM, Al-Alshaikh MA, Habib EE, El-Emam AA. Molecules 20 8125-8143 (2015)
  5. Antidepressant potential of nitrogen-containing heterocyclic moieties: An updated review. Siddiqui N, Andalip, Bawa S, Ali R, Afzal O, Akhtar MJ, Azad B, Kumar R. J Pharm Bioallied Sci 3 194-212 (2011)
  6. Discovery of 2-Alkyl-1-arylsulfonylprolinamides as 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors. Yu J, Liu H, Xia G, Liu L, Xu Z, Chen Q, Ma C, Sun X, Xu J, Li H, Li P, Shi Y, Xiong B, Liu X, Shen J. ACS Med Chem Lett 3 793-798 (2012)
  7. Design, synthesis and SAR of piperidyl-oxadiazoles as 11β-hydroxysteroid dehydrogenase 1 inhibitors. Xia G, You X, Liu L, Liu H, Wang J, Shi Y, Li P, Xiong B, Liu X, Shen J. Eur J Med Chem 62 1-10 (2013)
  8. Protlego: A Python package for the analysis and design of chimeric proteins. Ferruz N, Noske J, Höcker B. Bioinformatics btab253 (2021)
  9. Synthesis and biological evaluation of cyclic sulfamide derivatives as 11β-hydroxysteroid dehydrogenase 1 inhibitors. Kim SH, Bok JH, Lee JH, Kim IH, Kwon SW, Lee GB, Kang SK, Park JS, Jung WH, Kim HY, Rhee SD, Ahn SH, Bae MA, Ha DC, Kim KY, Ahn JH. ACS Med Chem Lett 3 88-93 (2012)
  10. 3-Amino-N-adamantyl-3-methylbutanamide derivatives as 11β-hydroxysteroid dehydrogenase 1 inhibitor. Lee Y, Shin YJ, Ahn SK. Bioorg. Med. Chem. Lett. 24 1421-1425 (2014)
  11. Antimicrobial and hypoglycemic activities of novel N-Mannich bases derived from 5-(1-adamantyl)-4-substituted-1,2,4-triazoline-3-thiones. Al-Abdullah ES, Al-Tuwaijri HM, Hassan HM, Haiba ME, Habib EE, El-Emam AA. Int J Mol Sci 15 22995-23010 (2014)
  12. Design, synthesis and in vivo study of novel pyrrolidine-based 11β-HSD1 inhibitors for age-related cognitive dysfunction. Leiva R, Griñan-Ferré C, Seira C, Valverde E, McBride A, Binnie M, Pérez B, Luque FJ, Pallàs M, Bidon-Chanal A, Webster SP, Vázquez S. Eur J Med Chem 139 412-428 (2017)
  13. Novel 11β-HSD1 inhibitors: C-1 versus C-2 substitution and effect of the introduction of an oxygen atom in the adamantane scaffold. Leiva R, Seira C, McBride A, Binnie M, Luque FJ, Bidon-Chanal A, Webster SP, Vázquez S. Bioorg. Med. Chem. Lett. 25 4250-4253 (2015)
  14. Design and synthesis of (R)-1-arylsulfonylpiperidine-2-carboxamides as 11β-hydroxysteroid dehydrogenase type 1 inhibitors. Xia G, Liu L, Liu H, Yu J, Xu Z, Chen Q, Ma C, Li P, Xiong B, Liu X, Shen J. ChemMedChem 8 577-581 (2013)
  15. Adamantane-Isothiourea Hybrid Derivatives: Synthesis, Characterization, In Vitro Antimicrobial, and In Vivo Hypoglycemic Activities. Al-Wahaibi LH, Hassan HM, Abo-Kamar AM, Ghabbour HA, El-Emam AA. Molecules 22 (2017)
  16. Novel 2-(Adamantan-1-ylamino)Thiazol-4(5H)-One Derivatives and Their Inhibitory Activity towards 11β-HSD1-Synthesis, Molecular Docking and In Vitro Studies. Studzińska R, Kupczyk D, Płaziński W, Baumgart S, Bilski R, Paprocka R, Kołodziejska R. Int J Mol Sci 22 8609 (2021)


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