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Benzopyrans as selective estrogen receptor beta agonists (SERBAs). Part 5: Combined A- and C-ring structure-activity relationship studies.

Richardson TI, Dodge JA, Wang Y, Durbin JD, Krishnan V, Norman BH
Bioorg Med Chem Lett 17 5563-6 (2007)
Cited: 18 times
EuropePMC logo PMID: 17804226

Abstract

Benzopyrans are selective estrogen receptor (ER) beta agonists (SERBAs), which bind the ER subtypes alpha and beta in opposite orientations. Here we describe the synthesis of a late stage intermediate that allowed us to combine A-ring and C-ring modifications and carry out simultaneous SAR studies at both positions. Modification of both positions proved additive, maintaining affinity and improving ERbeta selectivity up to 83-fold. An X-ray cocrystal structure confirms the previously observed binding mode in ERbeta.

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  1. Development of subtype-selective oestrogen receptor-based therapeutics. Nilsson S, Koehler KF, Gustafsson JÅ. Nat Rev Drug Discov 10 778-792 (2011)
  2. Estrogen receptor β ligands: recent advances and biomedical applications. Minutolo F, Macchia M, Katzenellenbogen BS, Katzenellenbogen JA. Med Res Rev 31 364-442 (2011)
  3. Versatility or promiscuity: the estrogen receptors, control of ligand selectivity and an update on subtype selective ligands. Ng HW, Perkins R, Tong W, Hong H. Int J Environ Res Public Health 11 8709-8742 (2014)
  4. Estrogen receptor beta selective nonsteroidal estrogens: seeking clinical indications. Mohler ML, Narayanan R, Coss CC, Hu K, He Y, Wu Z, Hong SS, Hwang DJ, Miller DD, Dalton JT. Expert Opin Ther Pat 20 507-534 (2010)
  5. A review on various aspects of organic synthesis using Comins' reagent. Devi Priya D, Lakshman C, Roopan SM. Mol Divers 26 691-716 (2022)

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  2. Diarylpropionitrile (DPN) enantiomers: synthesis and evaluation of estrogen receptor β-selective ligands. Carroll VM, Jeyakumar M, Carlson KE, Katzenellenbogen JA. J. Med. Chem. 55 528-537 (2012)
  3. Enantioselective organocatalytic domino Michael-acetalization-Henry reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of tetrahydro-6H-benzo[c]chromenones. Hong BC, Kotame P, Liao JH. Org. Biomol. Chem. 9 382-386 (2011)
  4. A convergent general strategy for the functionalized 2-aryl cycloalkyl-fused chromans: intramolecular hetero-Diels-Alder reactions of ortho-quinone methides. Tummatorn J, Ruchirawat S, Ploypradith P. Chemistry 16 1445-1448 (2010)
  5. Facile synthesis of 4-substituted 3,4-dihydrocoumarins via an organocatalytic double decarboxylation process. Peng S, Wang L, Guo H, Sun S, Wang J. Org. Biomol. Chem. 10 2537-2541 (2012)
  6. Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application. Cohen DT, Johnston RC, Rosson NT, Cheong PH, Scheidt KA. Chem. Commun. (Camb.) 51 2690-2693 (2015)
  7. Tricyclic flavonoids with 1,3-dithiolium substructure. Bahrin LG, Jones PG, Hopf H. Beilstein J Org Chem 8 1999-2003 (2012)
  8. Synthesis and biological evaluation of two agents for imaging estrogen receptor β by positron emission tomography: challenges in PET imaging of a low abundance target. Lee JH, Peters O, Lehmann L, Dence CS, Sharp TL, Carlson KE, Zhou D, Jeyakumar M, Welch MJ, Katzenellenbogen JA. Nucl. Med. Biol. 39 1105-1116 (2012)
  9. A precisely substituted benzopyran targets androgen refractory prostate cancer cells through selective modulation of estrogen receptors. Kumar R, Verma V, Sharma V, Jain A, Singh V, Sarswat A, Maikhuri JP, Sharma VL, Gupta G. Toxicol. Appl. Pharmacol. 283 187-197 (2015)


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