71033-50-6Relevant academic research and scientific papers
Synthesis and antiestrogenic activity of [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl][4-[2-(1-pyrrolidinyl) ethoxy]-phenyl]methanone, methanesulfonic acid salt
Jones,Suarez,Massey,Black,Tinsley
, p. 962 - 966 (1979)
Acylation of the sodio anion of β-tetralone with phenyl anisoate, followed by a Grignard reaction of the resultant 4 with 4-methoxyphenylmagnesium bromide, gave rise to two novel dihydronaphthalene isomers 5 and 6. Regioselective demethylation of either 5 or 6 by NaSEt produced [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl](4-hydroxyphenyl)methanone (7). Etherification of the phenolic group of 6duced [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl](4-hydroxyphenyl)methanone (7). Etherification of the phenolic group of 7 by N-(2-chloroethyl)pyrrolidine and subsequent methanesulfonate salt formation provided [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl][4-2-(1-pyrrolidinyl)ethoxy]phenyl]methanone, methane sulfonic acid salt. Potent antiestrogenic activity of 3 was demonstrated by both oral and subcutaneous administration to rats and mice. In vitro binding studies with rat uterine cystosol estrogen receptors indicate compound 3 has a very high binding affinity which exceeds that of estradiol.
