methallenestril

Methallenestril () (brand names Cur-men, Ercostrol, Geklimon, Novestrine, Vallestril), also known as methallenoestril () and as methallenestrol, as well as '''Horeau's acid, is a synthetic nonsteroidal estrogen and a derivative of allenolic acid and allenestrol (specifically, a methyl ether of it) that was formerly used to treat menstrual issues but is now no longer marketed. It is a seco-analogue of bisdehydrodoisynolic acid, and although methallenestril is potently estrogenic in rats, in humans it is only weakly so in comparison. Vallestril was a brand of methallenestril issued by G. D. Searle & Company in the 1950s. Methallenestril is taken by mouth. By the oral route, a dose of 25 mg methallenestril is approximately equivalent to 1 mg diethylstilbestrol, 4 mg dienestrol, 20 mg hexestrol, 25 mg estrone, 2.5 mg conjugated estrogens, and 0.05 mg ethinylestradiol.

==Synthesis== The chemical synthesis has been described: Patent: Unavailable methods: center|500px The Grignard reaction between 2-propionyl-6-methoxynaphthalene (promen) [2700-47-2] (1) and Ethyl 2-bromoisobutyrate [600-00-0] (2) occurs to give Ethyl beta-ethyl-beta-hydroxy-6-methoxy-alpha,alpha-dimethylnaphthalene-2-propionate [85536-81-8] (3). Dehydration of the carbinol in aqueous lye may be accompanied by saponification of the ester (although not in the patented version) to give [60533-05-3] (4). Re-esterification with diazomethane gave (5). Catalytic hydrogenation of the olefin led to PC608080 (6). Saponification of the ester completed the synthesis of Methallenestril (7''').