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. 1976 Aug;57(4):487–493. doi: 10.1111/j.1476-5381.1976.tb10375.x

Oestrogenic, anti-oestrogenic and fertility effects of some triphenylethanes and triphenylethylenes related to ethamoxytriphetol (MER 25).

E R Clark, V C Jordan
PMCID: PMC1667047  PMID: 963337

Abstract

Five triphenylethylenes, a triphenylethane and a triphenylethanol, carrying methyl substituents ortho to one or both of the ring oxygen functions, have been examined for oestrogenic, and antioestrogenic activity in mice, and three of the compounds, alpha-[4-(beta-diethylaminoethoxy)-3, 5-xylyl]-alpha-phenyl-beta-4-methoxyphenyl-ethanol (IV), alpha'-[4-(beta-diethylaminoethoxy)-3, 5-xylyl]-4-methoxy-bibenzyl (V) and alpha'-[4-(beta-diethylaminoethoxy)-3, 5-xylyl]-4-methoxy-stilbene (VI), were tested for their effects on fertility in mice. 2 Orthomethylation reduces oestrogenic and/or anti-oestrogenic activity compared with the reported activities of non-methylated analogues. 3 The anti-oestrogenic ethamoxytriphetol (MER 25) reduced fertility in mice whereas its inactive dimethylated analogue (IV) was ineffective. The weakly active anti-oestrogens, V and VI, did not affect fertility in mice.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BARNES L. E., MEYER R. K. Effects of ethamoxytriphetol, MRL-37, and clomiphene on reproduction in rats. Fertil Steril. 1962 Sep-Oct;13:472–480. doi: 10.1016/s0015-0282(16)34632-5. [DOI] [PubMed] [Google Scholar]
  2. Callantine M. R., Humphrey R. R., Lee S. L., Windsor B. L., Schottin N. H., O'Brien O. P. Action of an estrogen antagonist on reproductive mechanisms in the rat. Endocrinology. 1966 Jul;79(1):153–167. doi: 10.1210/endo-79-1-153. [DOI] [PubMed] [Google Scholar]
  3. Clark E. R., Evans J. G., Jordan V. C. Anti-oestrogenic activity in compounds related to ethamoxytriphetol (MER 25), clomiphene and MRL 37. Br J Pharmacol. 1973 Jun;48(2):345P–345P. [PMC free article] [PubMed] [Google Scholar]
  4. Clark E. R., McCracken A. M. [The oestrogenic and anti-oestrogenic properties of ring methyl-substituted stilboestrols]. J Pharm Pharmacol. 1971 May;23(5):339–346. doi: 10.1111/j.2042-7158.1971.tb09924.x. [DOI] [PubMed] [Google Scholar]
  5. Clark E. R., O'Donnell S. R. Oestrogenic and anti-oestrogenic activities of some hex-2-enes related to diethylstilboestrol. J Endocrinol. 1965 Nov;33(3):535–536. doi: 10.1677/joe.0.0330535. [DOI] [PubMed] [Google Scholar]
  6. Coggon P., McPhail A. T., Roe A. M. Conformation of xylocholine. Nature. 1969 Dec 20;224(5225):1200–1201. doi: 10.1038/2241200a0. [DOI] [PubMed] [Google Scholar]
  7. Collins D. J., Hobbs J. J., Emmens C. W. Antiestrogenic and antifertility compounds. 4. 1,1,2-Triarylalkan-1-ols and 1,1,2-Triarylalk-1-enes containing basic ether groups. J Med Chem. 1971 Oct;14(10):952–957. doi: 10.1021/jm00292a016. [DOI] [PubMed] [Google Scholar]
  8. EMMENS C. W., COX R. I., MARTIN L. Oestrogen inhibition by steroids and other substances. J Endocrinol. 1960 May;20:198–209. doi: 10.1677/joe.0.0200198. [DOI] [PubMed] [Google Scholar]
  9. Emmens C. W., Collins D. J., Hobbs J. J., Miller B. G., Owen W. H. Antiestrogenic and antifertility properties of some basic ether derivatives of dimethylstilbestrol and related compounds. J Pharmacol Exp Ther. 1969 Jan;165(1):52–59. [PubMed] [Google Scholar]
  10. Emmens C. W., Humphrey K., Martin L., Owen W. H. Antifertility properties of two non-oestrogenic steroids and MRL 37. Steroids. 1967 Feb;9(2):235–243. doi: 10.1016/0039-128x(67)90044-x. [DOI] [PubMed] [Google Scholar]
  11. Harper M. J., Walpole A. L. Contrasting endocrine activities of cis and trans isomers in a series of substituted triphenylethylenes. Nature. 1966 Oct 1;212(5057):87–87. doi: 10.1038/212087a0. [DOI] [PubMed] [Google Scholar]
  12. LERNER L. J., HOLTHAUS F. J., Jr, THOMPSON C. R. A non-steroidal estrogen antiagonist 1-(p-2-diethylaminoethoxyphenyl)-1-phenyl-2-p-methoxyphenyl ethanol. Endocrinology. 1958 Sep;63(3):295–318. doi: 10.1210/endo-63-3-295. [DOI] [PubMed] [Google Scholar]
  13. Lednicer D., Lyster S. C., Duncan G. W. Mammalian antifertility agents. IV. Basic 3,4-dihydronaphthalenes and 1,2,3,4-tetrahydro-1-naphthols. J Med Chem. 1967 Jan;10(1):78–84. doi: 10.1021/jm00313a016. [DOI] [PubMed] [Google Scholar]
  14. MARTIN L., EMMENS C. W., COX R. I. The effects of oestrogens and anti-oestrogens on early pregnancy in mice. J Endocrinol. 1960 Jun;20:299–306. doi: 10.1677/joe.0.0200299. [DOI] [PubMed] [Google Scholar]
  15. Terenius L. Structure-activity relationships of anti-oestrogens with regard to interaction with 17-beta-oestradiol in the mouse uterus and vagina. Acta Endocrinol (Copenh) 1971 Mar;66(3):431–447. doi: 10.1530/acta.0.0660431. [DOI] [PubMed] [Google Scholar]

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