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Nature of the C/D-Ring Union in the Œstrogenic Hormones

Nature volume 160, pages 6466 (12 July 1947) | Download Citation

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Abstract

There are certain types of biological activity (carcinogenic, œstrogenic, androgenic, progestational and cortical) in which, although little or nothing is known of the mechanism of action, the chemical structures of the primary agents are rather precisely known. While potent carcinogenic and œstrogenic activity is characterized by very low specificity to molecular type, and high androgenic, progestational, and cortical activity is associated in each case with a single specific molecular type, all five types of activity are sensitive to stereochemical structural modification. Thus deoxycorticosterone acetate (I) possesses high cortical activity, whereas 17-isodeoxycorticOsterone acetate (II), which differs only in configuration at C17, is completely inactive1; similarly the activity of progesterone (III) disappears entirely in the epimeric 17-isoprogesterone (IV)2.

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References

  1. 1.

    , Helv. Chim. Acta, 23, 925 (1940).

  2. 2.

    , , and , Ber., 72, 1112 (1939).

  3. 3.

    , and , Helv. Chim. Acta, 19, 842 (1936).

  4. 4.

    , "Encyclopædia of Endocrinology", Section 1, 4, Synoptic Charts, p. 12 (Montreal, 1943).

  5. 5.

    , , , , and , Naturwiss., 27, 131 (1939). , , , , and , Proc. Roy. Soc., B, 132, 83 (1944).

  6. 7.

    , , , , , and , Helv. Chim. Acta, 27, 1727 (1944); 28, 156, 991, 1326, 1506 (1945); 29, 586, 859, 1071, 1231, 1889 (1946); 30, 413 (1947).

  7. 8.

    , and , Helv. Chim. Acta, 29, 1894 (1946).

  8. 9.

    , , and , J. Amer. Chem. Soc., 62, 824 (1940).

  9. 10.

    , and , Ber., 74, 520 (1941).

  10. 11.

    , and , Z. physiol. Chem., 216, 91 (1933).

  11. 13.

    , and , Ber., 74, 1911 (1941); 76, 233 (1943).

  12. 14.

    , and , J. Amer. Chem. Soc., 68, 2125 (1946).

  13. 16.

    , , , and , J. Amer. Chem. Soc., 58, 1503 (1936).

  14. 17.

    , J. Amer. Chem. Soc., 60, 1897 (1938).

  15. 18.

    , , and , Ber., 74, 1308 (1941).

  16. 19.

    , , and , Ber., 75, 1931 (1942); 77, 392 (1944).

  17. 6.

    , private communication.

  18. 12.

    Intelligence Report No. 245, Office of Publication Board, U.S. Dept. of Commerce.

  19. 15.

    Combined Intelligence Objectives Sub-Committee, Item 24, File XXV-54, 20 (1945).

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Affiliations

  1. Chester Beatty Research Institute, Royal Cancer Hospital (Free), London, S.W.3

    • C. W. SHOPPEE

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https://doi.org/10.1038/160064a0

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