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Discovery of potent, orally-active, and muscle-selective androgen receptor modulators based on an N-aryl-hydroxybicyclohydantoin scaffold.

Sun C, Robl JA, Wang TC, Huang Y, Kuhns JE, Lupisella JA, Beehler BC, Golla R, Sleph PG, Seethala R, Fura A, Krystek SR, An Y, Malley MF, Sack JS, Salvati ME, Grover GJ, Ostrowski J, Hamann LG
J Med Chem 49 7596-9 (2006)
Cited: 31 times
EuropePMC logo PMID: 17181141

Abstract

A novel, N-aryl-bicyclohydantoin selective androgen receptor modulator scaffold was discovered through structure-guided modifications of androgen receptor antagonists. A prototype compound (7R,7aS)-10b from this series is a potent and highly tissue-selective agonist of the androgen receptor. After oral dosing in a rat atrophied levator ani muscle model, (7R,7aS)-10b demonstrated efficacy at restoring levator ani muscle mass to that of intact controls and exhibited >50-fold selectivity for muscle over prostate.

Reviews - 2ihq mentioned but not cited (1)

  1. Selective androgen receptor modulators in preclinical and clinical development. Narayanan R, Mohler ML, Bohl CE, Miller DD, Dalton JT. Nucl Recept Signal 6 e010 (2008)

Articles - 2ihq mentioned but not cited (4)

  1. Structure of the homodimeric androgen receptor ligand-binding domain. Nadal M, Prekovic S, Gallastegui N, Helsen C, Abella M, Zielinska K, Gay M, Vilaseca M, Taulès M, Houtsmuller AB, van Royen ME, Claessens F, Fuentes-Prior P, Estébanez-Perpiñá E. Nat Commun 8 14388 (2017)
  2. Computational Analysis of Residue-Specific Binding Free Energies of Androgen Receptor to Ligands. Shao G, Bao J, Pan X, He X, Qi Y, Zhang JZH. Front Mol Biosci 8 646524 (2021)
  3. An Assay on the Possible Effect of Essential Oil Constituents on Receptors Involved in Women's Hormonal Health and Reproductive System Diseases. Sakhteman A, Pasdaran A, Afifi M, Hamedi A. J Evid Based Integr Med 25 2515690X20932527 (2020)
  4. Yuel: Improving the Generalizability of Structure-Free Compound-Protein Interaction Prediction. Wang J, Dokholyan NV. J Chem Inf Model 62 463-471 (2022)


Reviews citing this publication (7)

  1. Nuclear receptor drug discovery. Chen T. Curr Opin Chem Biol 12 418-426 (2008)
  2. Mass spectrometry of selective androgen receptor modulators. Thevis M, Schänzer W. J Mass Spectrom 43 865-876 (2008)
  3. AR, apoE, and cognitive function. Raber J. Horm Behav 53 706-715 (2008)
  4. Recent developments in antiandrogens and selective androgen receptor modulators. Haendler B, Cleve A. Mol Cell Endocrinol 352 79-91 (2012)
  5. Androgen receptor as a therapeutic target. Gao W. Adv Drug Deliv Rev 62 1277-1284 (2010)
  6. Recent advances in the development of selective androgen receptor modulators. Zhang X, Lanter JC, Sui Z. Expert Opin Ther Pat 19 1239-1258 (2009)
  7. Developments in nonsteroidal antiandrogens targeting the androgen receptor. Liu B, Su L, Geng J, Liu J, Zhao G. ChemMedChem 5 1651-1661 (2010)

Articles citing this publication (19)

  1. Emerging drugs: mechanism of action, mass spectrometry and doping control analysis. Thevis M, Thomas A, Kohler M, Beuck S, Schänzer W. J Mass Spectrom 44 442-460 (2009)
  2. Determination of benzimidazole- and bicyclic hydantoin-derived selective androgen receptor antagonists and agonists in human urine using LC-MS/MS. Thevis M, Kohler M, Thomas A, Maurer J, Schlörer N, Kamber M, Schänzer W. Anal Bioanal Chem 391 251-261 (2008)
  3. Mass spectrometry of hydantoin-derived selective androgen receptor modulators. Thevis M, Kohler M, Schlörer N, Kamber M, Kühn A, Linscheid MW, Schänzer W. J Mass Spectrom 43 639-650 (2008)
  4. Screening for two selective androgen receptor modulators using gas chromatography-mass spectrometry in doping control analysis. Thevis M, Kohler M, Schlörer N, Fusshöller G, Schänzer W. Eur J Mass Spectrom (Chichester) 14 153-161 (2008)
  5. Molecular determinants of the recognition of ulipristal acetate by oxo-steroid receptors. Petit-Topin I, Fay M, Resche-Rigon M, Ulmann A, Gainer E, Rafestin-Oblin ME, Fagart J. J Steroid Biochem Mol Biol 144 Pt B 427-435 (2014)
  6. A selective androgen receptor modulator with minimal prostate hypertrophic activity enhances lean body mass in male rats and stimulates sexual behavior in female rats. Allan GF, Tannenbaum P, Sbriscia T, Linton O, Lai MT, Haynes-Johnson D, Bhattacharjee S, Zhang X, Sui Z, Lundeen SG. Endocrine 32 41-51 (2007)
  7. Tandem optimization of target activity and elimination of mutagenic potential in a potent series of N-aryl bicyclic hydantoin-based selective androgen receptor modulators. Hamann LG, Manfredi MC, Sun C, Krystek SR, Huang Y, Bi Y, Augeri DJ, Wang T, Zou Y, Betebenner DA, Fura A, Seethala R, Golla R, Kuhns JE, Lupisella JA, Darienzo CJ, Custer LL, Price JL, Johnson JM, Biller SA, Zahler R, Ostrowski J. Bioorg Med Chem Lett 17 1860-1864 (2007)
  8. Expanding sports drug testing assays: mass spectrometric characterization of the selective androgen receptor modulator drug candidates RAD140 and ACP-105. Thevis M, Piper T, Beuck S, Geyer H, Schänzer W. Rapid Commun Mass Spectrom 27 1173-1182 (2013)
  9. Synthesis and biological evaluation of novel selective androgen receptor modulators (SARMs). Part I. Aikawa K, Miyawaki T, Hitaka T, Imai YN, Hara T, Miyazaki J, Yamaoka M, Kusaka M, Kanzaki N, Tasaka A, Shiraishi M, Yamamoto S. Bioorg Med Chem 23 2568-2578 (2015)
  10. 4-(Anilino)pyrrole-2-carboxamides: Novel non-steroidal/non-anilide type androgen antagonists effective upon human prostate tumor LNCaP cells with mutated nuclear androgen receptor. Wakabayashi K, Imai K, Miyachi H, Hashimoto Y, Tanatani A. Bioorg Med Chem 16 6799-6812 (2008)
  11. Synthesis and SAR of tetrahydropyrrolo[1,2-b][1,2,5]thiadiazol-2(3H)-one 1,1-dioxide analogues as highly potent selective androgen receptor modulators. Manfredi MC, Bi Y, Nirschl AA, Sutton JC, Seethala R, Golla R, Beehler BC, Sleph PG, Grover GJ, Ostrowski J, Hamann LG. Bioorg Med Chem Lett 17 4487-4490 (2007)
  12. A selective androgen receptor modulator with minimal prostate hypertrophic activity restores lean body mass in aged orchidectomized male rats. Allan G, Sbriscia T, Linton O, Lai MT, Haynes-Johnson D, Bhattacharjee S, Ng R, Sui Z, Lundeen S. J Steroid Biochem Mol Biol 110 207-213 (2008)
  13. Potent, nonsteroidal selective androgen receptor modulators (SARMs) based on 8H-[1,4]oxazino[2,3-f]quinolin-8-ones. Higuchi RI, Thompson AW, Chen JH, Caferro TR, Cummings ML, Deckhut CP, Adams ME, Tegley CM, Edwards JP, López FJ, Kallel EA, Karanewsky DS, Schrader WT, Marschke KB, Zhi L. Bioorg Med Chem Lett 17 5442-5446 (2007)
  14. Discovery of a novel series of nonsteroidal androgen receptor modulators: 5- or 6-oxachrysen-2-ones. Zhao S, Shen Y, van Oeveren A, Marschke KB, Zhi L. Bioorg Med Chem Lett 18 3431-3435 (2008)
  15. Effects of the SARM ACP-105 on rotorod performance and cued fear conditioning in sham-irradiated and irradiated female mice. Dayger C, Villasana L, Pfankuch T, Davis M, Raber J. Brain Res 1381 134-140 (2011)
  16. Synthesis and biological evaluation of novel selective androgen receptor modulators (SARMs) Part III: Discovery of 4-(5-oxopyrrolidine-1-yl)benzonitrile derivative 2f as a clinical candidate. Aikawa K, Asano M, Ono K, Habuka N, Yano J, Wilson K, Fujita H, Kandori H, Hara T, Morimoto M, Santou T, Yamaoka M, Nakayama M, Hasuoka A. Bioorg Med Chem 25 3330-3349 (2017)
  17. LiAlH4 -Induced Selective Ring Rearrangement of 2-(2-Cyanoethyl)aziridines toward 2-(Aminomethyl)pyrrolidines and 3-Aminopiperidines as Eligible Heterocyclic Building Blocks. Dolfen J, Vervisch K, De Kimpe N, D'hooghe M. Chemistry 22 4945-4951 (2016)
  18. Selective androgen receptor modulators based on a series of 7H-[1,4]oxazino[3,2-g]quinolin-7-ones with improved in vivo activity. Long YO, Higuchi RI, Caferro TR, Lau TL, Wu M, Cummings ML, Martinborough EA, Marschke KB, Chang WY, López FJ, Karanewsky DS, Zhi L. Bioorg Med Chem Lett 18 2967-2971 (2008)
  19. Structural basis for computational screening of non-steroidal androgen receptor ligands. Nyrönen TH, Söderholm AA. Expert Opin Drug Discov 5 5-20 (2010)


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