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Abstract
The important cytochrome P450 inhibitor ancymidol is used as a plant growth retardant and has potential for various medicinal applications. However its high price sets economic limits to large-scale applications. Here a short and high-yielding synthesis is reported, providing ancymidol in substantial amounts in a cost- and time-efficient way.
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References
- BLOCK, D.L. 1981. The Chemistry of the Sulphonium Group. In: The Chemistry of the Sulphonium Group (Ed. by Stirling, J. W.), pp. 680-702. New York: Wiley.
- CASEY, M., LEONARD, J., LYGO, B. and PROCTER, G. 1990. Advanced Practical Organic Chemistry. New York: Chapman and Hall.
- CLOSE, W.J. 1957. An improved synthesis of cyclopropyl phenyl ketone and related substances J. Am. Chem. Soc., 79, 1455-1458.
- COOLBAUGH, R. C., HIRANO, S. S. and WEST, C. A. 1978. Studies on the specificity and site of action of ancymidol, a plant growth regulator. Plant Physiol., 62: 571-576.
- COREY, E.J. and CHAYKOVSKY, D.L. 1965. Dimethyloxosulfonium methylide and dimethylsulfonium methylide. Formation and application to organic synthesis. J. Am. Chem. Soc., 87, 1353-1364.
- COULSON, C.J., KING, D.J. and WISEMAN, A. 1984. Chemotherapeutic and agrochemical applications of cytochrome P-450 ligands. Trends Biochem. Sci., 10: 446-449.
- DAVENPORT, J.D., HACKLER, R.E. and TAYLOR, H.M. 1968. Fungicidal 5-substituted pyrimidines, European Patent Application (for: Eli Lilly & Co., Greenfield, IN, USA).
- MURPHY, P.J. and WEST, C.A. 1978. An enzymic site of inhibition of gibberellin biosynthesis by Amo 1618 and other plant growth retardants Plant Physiol., 62: 571-576.
- ORTIZ-DE-MONTELLANO, P.R. 1988. Suicide Substrates for Drug Metabolizing Enzymes: Mechanisms and Biological Consequences. In: Progress in Drug Metabolism (Ed. by Gibson, G.G.), pp. 99-148. London: Taylor & Francis.
- ORTIZ-DE-MONTELLANO, P.R. and REICH, N.O. 1986. Inhibition of Cytochrome P450 Enzymes. In: Cytochrome P450 (Ed. by Ortiz-de-Montellano, P. R.), pp. 273-314. New York: Plenum Press.
- PATZELT, H. and ROBINSON, J.A. 1993. Biosynthesis of the Polyether Antibiotic Monensin A: Incorporation of a Polyketide Chain Elongation Intermediate. J. Chem. Soc.; Chem. Commun., 1258-1260.
- PERRIN, D.D. and ARMAREGO, W.L. F. 1988. Purification of Laboratory Chemicals. Oxford, UK: Pergamon Press.
- RADEMACHER, W. 2000. Growth retardants: Effects on gibberellin biosynthesis and other metabolic pathways. Annu. Rev. Plant Physiol. Plant Molec. Biol, 51: 501-531.
- SANTELLI, M. and BERTRAND, M. 1973. Synthèse d'alcools ß-alléniques par réduction des ènes-2 yne-4 ols-1. Première partie. Bull. Soc. Chim. Fr., 2331-2335.
- TAYLOR, H.M., JONES, C.D., DAVENPORT, J.D., HIRSCH, K.S., KRESS, T.J. and WEAVER, D. 1987. Aromatase Inhibition by 5-Substituted Pyrimidines and Dihydropyrimidines. J. Med. Chem., 30: 1359-1365.
- TESTA, B. and JENNER, P. 1981. Inhibitors of Cytochrome P450s and their Mechanims of Action. Drug Metabol. Rev., 12: 1-117.
- TROST, B.M. and MELVIN, K.L. 1975. Sulfur Ylides. New York: Academic Press.
References
BLOCK, D.L. 1981. The Chemistry of the Sulphonium Group. In: The Chemistry of the Sulphonium Group (Ed. by Stirling, J. W.), pp. 680-702. New York: Wiley.
CASEY, M., LEONARD, J., LYGO, B. and PROCTER, G. 1990. Advanced Practical Organic Chemistry. New York: Chapman and Hall.
CLOSE, W.J. 1957. An improved synthesis of cyclopropyl phenyl ketone and related substances J. Am. Chem. Soc., 79, 1455-1458.
COOLBAUGH, R. C., HIRANO, S. S. and WEST, C. A. 1978. Studies on the specificity and site of action of ancymidol, a plant growth regulator. Plant Physiol., 62: 571-576.
COREY, E.J. and CHAYKOVSKY, D.L. 1965. Dimethyloxosulfonium methylide and dimethylsulfonium methylide. Formation and application to organic synthesis. J. Am. Chem. Soc., 87, 1353-1364.
COULSON, C.J., KING, D.J. and WISEMAN, A. 1984. Chemotherapeutic and agrochemical applications of cytochrome P-450 ligands. Trends Biochem. Sci., 10: 446-449.
DAVENPORT, J.D., HACKLER, R.E. and TAYLOR, H.M. 1968. Fungicidal 5-substituted pyrimidines, European Patent Application (for: Eli Lilly & Co., Greenfield, IN, USA).
MURPHY, P.J. and WEST, C.A. 1978. An enzymic site of inhibition of gibberellin biosynthesis by Amo 1618 and other plant growth retardants Plant Physiol., 62: 571-576.
ORTIZ-DE-MONTELLANO, P.R. 1988. Suicide Substrates for Drug Metabolizing Enzymes: Mechanisms and Biological Consequences. In: Progress in Drug Metabolism (Ed. by Gibson, G.G.), pp. 99-148. London: Taylor & Francis.
ORTIZ-DE-MONTELLANO, P.R. and REICH, N.O. 1986. Inhibition of Cytochrome P450 Enzymes. In: Cytochrome P450 (Ed. by Ortiz-de-Montellano, P. R.), pp. 273-314. New York: Plenum Press.
PATZELT, H. and ROBINSON, J.A. 1993. Biosynthesis of the Polyether Antibiotic Monensin A: Incorporation of a Polyketide Chain Elongation Intermediate. J. Chem. Soc.; Chem. Commun., 1258-1260.
PERRIN, D.D. and ARMAREGO, W.L. F. 1988. Purification of Laboratory Chemicals. Oxford, UK: Pergamon Press.
RADEMACHER, W. 2000. Growth retardants: Effects on gibberellin biosynthesis and other metabolic pathways. Annu. Rev. Plant Physiol. Plant Molec. Biol, 51: 501-531.
SANTELLI, M. and BERTRAND, M. 1973. Synthèse d'alcools ß-alléniques par réduction des ènes-2 yne-4 ols-1. Première partie. Bull. Soc. Chim. Fr., 2331-2335.
TAYLOR, H.M., JONES, C.D., DAVENPORT, J.D., HIRSCH, K.S., KRESS, T.J. and WEAVER, D. 1987. Aromatase Inhibition by 5-Substituted Pyrimidines and Dihydropyrimidines. J. Med. Chem., 30: 1359-1365.
TESTA, B. and JENNER, P. 1981. Inhibitors of Cytochrome P450s and their Mechanims of Action. Drug Metabol. Rev., 12: 1-117.
TROST, B.M. and MELVIN, K.L. 1975. Sulfur Ylides. New York: Academic Press.