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Alkylating esters VIII. The action of the isomers of dimethylmyleran on spermatogenesis

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Zusammenfassung

Als Antifertilitätsmittel haben dasmeso-Isomer und die (±)-Isomere von Dimethylmyleran eine synergistische Wirkung auf die Spermatogenese von Ratten. Bei Mäusen und Wachteln hat ein 50% iges Gemisch der Isomere eine niedrigere Toxizität als die einzelnen Isomere, was bei höherer Dosis des Gemisches zu längerdauernder Sterilität führt.

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Literatur

  1. A. R. Jones, Chem. Commun.1971, 1042.

  2. A. R. Jones, Chem.-biol. Interact.6, 47 (1973).

    Article  CAS  Google Scholar 

  3. H. Jackson, B. W. Fox andA. W. Craig, J. Reprod. Fertil.2, 447 (1961).

    Article  CAS  Google Scholar 

  4. H. Jackson,Antifertility Compounds in the Male and Female (Thomas, Springfield Illinois, 1966), p. 63.

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  5. The usual synthesis of DMM involves the methanesulphonylation of hexane-2, 5-diol and recrystallization of the precipitated ester from alcohol. The precipitate is mainlymeso-DMM but contains, together with mother liquors, an equi-molar amount of (±)-DMM.

  6. The (+)- and (−)-isomers of DMM were synthesised from (+)-and (−)-hexane-2,5-diol. The (±)-diol was resolved through the brucine salt of the bis (monophthallate) ester according toDodson andNelson. Optical purity, by comparison to authentic values, was 80% for the (+)-and 83% for the (−)-isomers respectively. Treatment for each diol with methanesulphonyl chloride in pyridine gave, respectively, (+)-DMM ((2R, 5R)-2,5-hexanedimethane-sulphonate) and (−)-DMM ((2S, 5S)-2,5-hexanedimethanesulphonate), both as white prisms from absolute alcohol, m.p. 44–7°C.

  7. R. M. Dodson andV. C. Nelson, J. org. Chem.33, 3966 (1968).

    Article  CAS  Google Scholar 

  8. K. Serck-Hanssen, S. Stallberg-Stenhagen andE. Stenhagen, Arkiv. kemi.5, 203 (1953).

    CAS  Google Scholar 

  9. P. Jones andH. Jackson, J. Reprod. Fertil.31, 319 (1972).

    Article  CAS  Google Scholar 

  10. M. Bock andH. Jackson, Br. J. Pharmac.12, 1 (1957).

    CAS  Google Scholar 

  11. P. Jones, E. Kominkova andH. Jackson, J. Reprod. Fertil.29, 71 (1972).

    Article  CAS  Google Scholar 

  12. G. L. Floersheim, Lancet,1, 228 (1969).

    Article  CAS  Google Scholar 

  13. Acknowledgement. This work was supported by grants from the Ford Foundation and the Medical Research Council.

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Authors and Affiliations

  1. Unit of Reproductive Pharmacology, University of Manchester, M13 9PT, Manchester, England

    A. R. Jones & P. Jones

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  1. A. R. Jones
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  2. P. Jones
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Jones, A.R., Jones, P. Alkylating esters VIII. The action of the isomers of dimethylmyleran on spermatogenesis. Experientia 30, 178–179 (1974). https://doi.org/10.1007/BF01927719

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