Preparation of highly substituted gamma-lactam follicle stimulating hormone receptor agonists.
An unusual combination of Weinreb amidation and Mitsunobu lactam formation was used to prepare highly substituted gamma-lactam analogues of a thiazolidinone follicle stimulating hormone receptor agonist. The analogue synthesis was stereoselective and the final products were chemically stable. Biological properties of the target molecules were nearly identical to those of the lead compound.
Pelletier
Jeffrey C
JC
Department of Chemical and Screening Sciences, Wyeth Research, Collegeville, PA 19426, USA. pelletj@wyeth.com
Rogers
John
J
Wrobel
Jay
J
Perez
M Claudia
MC
Shen
Emily S
ES
D000577:Amides / Q000737:chemistry; D000242:Cyclic AMP / Q000096:biosynthesis; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D011962:Receptors, FSH / Q000819:agonists* / Q000378:metabolism; D013379:Substrate Specificity
D000577:Amides; D007769:Lactams; D011962:Receptors, FSH; D000242:Cyclic AMP