Seco-oestradiols and some non-steroidal oestrogens: structural correlates of oestrogenic action.
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Biomedical subjects
Publications and source records attributed to S Ray.
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A rapid gas chromatographic technique has been developed for quantitative estimation of cyclic N-nitrosamines. Cumbersome clean-up procedures are unnecessary and quantitative estimation can be done by injecting hexane extract without further pretreatment. The detection limit for the procedures is ca. 0.5 ng.
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Plasma cortisol level and intraocular tension were determined diurnally in 40 normal and 40 glaucomatous patients at 8 AM and 8 PM. It was observed that (1) plasma cortisol level was higher in glaucomatous patients at both the periods; (2) the diurnal variation in plasma cortisol was parallel to diurnal variation in intraocular tension in both glaucomatous and normal persons; and (3) the diurnal variation in plasma cortisol level also was more marked in glaucomatous patients as compared to normal persons.
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Synthesis and antiimplantation activity of variously substituted 2,2-dialkyl-3,4-diphenylchromenes and 3,4-cis- and trans-chromans derived from them are described. Pregnancy-inhibiting activity in rats was exhibited by a number of these compounds, which was particularly marked in the case of 3,4-trans-3-phenyl-4-p-(beta-pyrrolidinoethoxy)-phenyl-7-methoxychroman (32), the corresponding 2,2-dimethyl analog 34, and 3-phenyl-4-p-(beta-pyrrolidinoethoxy)phenyl-7-methoxychromene (26). The structure-activity relationship of these compounds is discussed.
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9,11-Secoestradiol (9) and 11-hydroxy-9,11-secoestradiol (12) have been synthesized starting from 17-acetoxyestradiol 3-methyl ether (1) and found to possess significant antifertility activity in rats. 3-Methoxy-9,11-seco-9-oxo-17beta-acetoxyestra-1,3,5(10)-trien-11-oic acid (2), prepared by CrO3 oxidation of 1, on hydrogenolysis gave methyl 17beta-hydroxy-3-methoxy-9,11-secoestra-1,3,5(10)-triene-11-carboxylate (3). The 17-O-THP derivative of 3 was treated with LiAlH4 to give 17beta-(O-tetrahydropyranyl)-3-methoxy-11-hydroxy-9,11-secoestra-1,3,5(10)-triene (5). The 11-O-mesylate of 5 on LiAlH4 reduction followed by mild acid treatment and demethylation under alkaline conditions gave 9. LiAlH4 reduction of 3 gave 9,11-seco-11-hydroxyestradiol 3-methyl ether (11) which on demethylation gave 9,11-seco-11-hydroxyestradiol (12).
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