Amide derivatives of 9,11-seco-estra-1,3,5(10)-trien-11-oic acid as modified orally active estrogen agonists with moderate antagonistic activity.
Synthesis of amide derivatives of 9,11-seco-estra-1,3,5(10)-trien-11-oic acid containing alkyl and aromatic amine residues has been carried out with an aim to prepare orally active estrogen antagonists. Modification of the estradiol molecule in the form of C-seco-amide derivatives has led to their high oral absorption. Compounds 7 an n-propyl amide, 8 an n-butyl amide, and 16 a p-anisidyl amide of C-seco-estrane showed significant estrogen antagonistic activity (>20%), while, the majority of compounds possessed high estrogen agonistic activity on oral administration at 10mg/kg dose in rats.
Negi
Arvind Singh
AS
Phytochemistry Division, Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Chaturvedi
Devdutt
D
Gupta
Atul
A
Ray
S
S
Dwivedy
Anila
A
Singh
M M
MM
D000284:Administration, Oral; D000577:Amides / Q000737:chemistry*; D000818:Animals; D004965:Estrogen Antagonists / Q000737:chemistry / Q000494:pharmacology; D004967:Estrogens / Q000819:agonists* / Q000737:chemistry; D004970:Estrone / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats
C500018:9,11-seco-estra-1,3,5(10)-trien-11-oic acid; D000577:Amides; D004965:Estrogen Antagonists; D004967:Estrogens; D004970:Estrone