109610-53-9Relevant academic research and scientific papers
Antifertility Agents: Part XLVI - Synthesis and Activity of 1,2-trans-1--2-phenyl-7-methoxybenzosuberan
Sangwan, Naresh K.,Prasad, Mohan,Rastogi, Shri Nivas,Jehan, Qaiser,Setty, B. S.
, p. 832 - 837 (2007/10/02)
Treatment of 1-bromo-3-(m-methoxyphenyl)propane (2) with p-methoxydesoxybenzoin and benzyl cyanide yields 1,5-diaryl-2-phenylpentanone (5) and 2,5-diarylpentanenitrile (6) respectively.Demethylation of 5 gives 1-(p-hydroxyphenyl)-3-(m-methoxyphenyl) (7) and 1-(p-hydroxyphenyl)-3-(m-hydroxyphenyl)-(8)-2-phenylpentanones which on acetylation afford mono- and di-acetates 9 and 10 respectively.Attempted cyclisation of 7 and 9 with p-TsOH fails to give the desired 1,2-diarylbenzosuber-1-ene (11).In another approach, 6 is hydrolysed to yield the acid 12 which on treatment with PPA gives 2-phenylbenzosuber-1-one (13) while with PCl5-SnCl4 it gives a mixture of 13 and 1-chloro-2-phenylbenzosuber-1-ene (14).Reaction of 13 and p-(trimethylsilyloxy)phenylmagnesium bromide gives 11 in a low yield.Alternatively, 13 is reduced with NaBH4 to give a cis-/trans-mixture of suberols 15a,b which on treatment with PhOH-AlCl3 yield mainly 1,2-trans-1-(p-hydroxyphenyl)-2-phenyl-7-methoxybenzosuberan (18) along with 2-phenylbenzosuber-1-ene (16) and traces of 1-(o-hydroxyphenyl)-2-phenylbenzosuberan (18a).Acetylation of 18 gives the acetate 19 and alkylation of 18 furnishes the desired compound, 1,2-trans-1--2-phenyl-7-methoxybenzosuberan (III, 20).The compound 20 prevents pregnancy in rats at 0.2 mg/kg daily oral dose on days 1-5 post-coitum or at a single oral dose of 1.5 mg/kg on day 1 post-coitum.At 0.2 mg/kg dose, it is 1000 times less estrogenic than ethinylestradiol and is antiestrogenic at single day contraceptive dose.
