H-D exchange of psilocin and its analogs

Heterocycles

Volumn 50, Issue 2, 1999, Pages 657-660

  Sogawa, Kazuyo ^a   Hashimoto, Kimiko ^a   Shirahama, Haruhisa ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYINDOLE; BUFOTENINE; METHANOL; PSILOCIN;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MUSHROOM; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0033117594     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-s(h)87     Document Type: Article

References (27)

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3. Isolation and characterization: A. Hofmann, R. Heim, A. Brack, and H. Kobel, Experientia, 1958, 14, 107. A. Hofmann, A. Frey, H. Ott, Th. Petrzilka, and F. Troxler, Experientia, 1958, 14, 397. A. Hofmann and F. Troxler, Experientia, 1959, 15, 101. A. Hofmann, R. Heim, A. Brack, H. Kobel, A. Frey, H. Ott, Th. Petrzilka, and F. Troxler, Helv. Chim. Acta, 1959, 42, 1557. Biosynthesis: S. Agurell and J. L. G. Nilsson, Acta Chem. Scand., 1968, 22, 1210. X-Ray analysis: H. P. Weber and T. J. Petcher, J. Chem. Soc., Perkin Trans. 2, 1974, 942 and 946.
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6. Isolation and characterization: A. Hofmann, R. Heim, A. Brack, and H. Kobel, Experientia, 1958, 14, 107. A. Hofmann, A. Frey, H. Ott, Th. Petrzilka, and F. Troxler, Experientia, 1958, 14, 397. A. Hofmann and F. Troxler, Experientia, 1959, 15, 101. A. Hofmann, R. Heim, A. Brack, H. Kobel, A. Frey, H. Ott, Th. Petrzilka, and F. Troxler, Helv. Chim. Acta, 1959, 42, 1557. Biosynthesis: S. Agurell and J. L. G. Nilsson, Acta Chem. Scand., 1968, 22, 1210. X-Ray analysis: H. P. Weber and T. J. Petcher, J. Chem. Soc., Perkin Trans. 2, 1974, 942 and 946.
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12. H. Blaschko and W. G. Levine, Biochem. Pharmacol., 1960, 3, 168. A. Horita and L. J. Weber, Biochem. Phamacol., 1961, 7, 47. L. J. Weber and A. Horita, Life Science, 1963, 44. L. P. Gilmour, R. D. O'Brien, Science, 1967, 155, 207. W. G. Levine, Nature, 1967, 215, 1292. R. G. Benedict, V. E. Tyler, and R. Watling, Lloydia, 1967, 30, 150, J. Gartz, Pharmazie, 1985, 40, 274.
13. H. Blaschko and W. G. Levine, Biochem. Pharmacol., 1960, 3, 168. A. Horita and L. J. Weber, Biochem. Phamacol., 1961, 7, 47. L. J. Weber and A. Horita, Life Science, 1963, 44. L. P. Gilmour, R. D. O'Brien, Science, 1967, 155, 207. W. G. Levine, Nature, 1967, 215, 1292. R. G. Benedict, V. E. Tyler, and R. Watling, Lloydia, 1967, 30, 150, J. Gartz, Pharmazie, 1985, 40, 274.
14. H. Blaschko and W. G. Levine, Biochem. Pharmacol., 1960, 3, 168. A. Horita and L. J. Weber, Biochem. Phamacol., 1961, 7, 47. L. J. Weber and A. Horita, Life Science, 1963, 44. L. P. Gilmour, R. D. O'Brien, Science, 1967, 155, 207. W. G. Levine, Nature, 1967, 215, 1292. R. G. Benedict, V. E. Tyler, and R. Watling, Lloydia, 1967, 30, 150, J. Gartz, Pharmazie, 1985, 40, 274.
15. H. Blaschko and W. G. Levine, Biochem. Pharmacol., 1960, 3, 168. A. Horita and L. J. Weber, Biochem. Phamacol., 1961, 7, 47. L. J. Weber and A. Horita, Life Science, 1963, 44. L. P. Gilmour, R. D. O'Brien, Science, 1967, 155, 207. W. G. Levine, Nature, 1967, 215, 1292. R. G. Benedict, V. E. Tyler, and R. Watling, Lloydia, 1967, 30, 150, J. Gartz, Pharmazie, 1985, 40, 274.
16. J. W. Daly and B. Witkop previously observed H-D exchange on hydroxyindoles under different conditions in relation to the NIH shift reaction. J. W. Daly and B. Witkop, J. Am. Chem. Soc., 1967, 89, 1032.
17. M. E. Speeter and W. C. Anthony, J. Am. Chem. Soc., 1954, 76, 6208.
18. T. Matsumoto, U. Nagashima, K. Tanabe, K. Hashimoto, K. Sogawa, and H. Shirahama, J. Comput. Chem., submitted.
19. Oxidation of some hydroxyindoles: A. Bertazzo, S. Catinella, and P. Traldi, J. Mass Spectrometry, 1996, 31, 735. A. Bertazzo, C. Costa, G. Allegri, D. Favretto, and P. Traldi, Rapid Commun. Mass Spectrometry, 1996, 10, 1299. T. Tabatabaie, R. N. Goyal, C. L. Blank and G. Dryhurst, J. Med. Chem., 1993, 36, 229. T. Tabatabaie and G. Dryhurst, J. Med. Chem., 1992, 35, 2261. T. Tabatabaie, M. Z. Wrona, and G. Dryhurst, J. Med. Chem., 1990, 33, 667. M. Z. Wrona and G. Dryhurst, J. Org. Chem., 1989, 54, 2718. G. Dryhurst, A. Anne, M. Z. Wrona, and D. Lemordant, J. Am. Chem. Soc., 1989, 111, 719. M. Z. Wrona, D. Lemordant, L. Lin, C. L. Blank, and G. Dryhurst, J. Med. Chem., 1986, 29, 499. A. K. Sinhababu and R. T. Borchardt, J. Am. Chem. Soc., 1985, 107, 7618.
20. Oxidation of some hydroxyindoles: A. Bertazzo, S. Catinella, and P. Traldi, J. Mass Spectrometry, 1996, 31, 735. A. Bertazzo, C. Costa, G. Allegri, D. Favretto, and P. Traldi, Rapid Commun. Mass Spectrometry, 1996, 10, 1299. T. Tabatabaie, R. N. Goyal, C. L. Blank and G. Dryhurst, J. Med. Chem., 1993, 36, 229. T. Tabatabaie and G. Dryhurst, J. Med. Chem., 1992, 35, 2261. T. Tabatabaie, M. Z. Wrona, and G. Dryhurst, J. Med. Chem., 1990, 33, 667. M. Z. Wrona and G. Dryhurst, J. Org. Chem., 1989, 54, 2718. G. Dryhurst, A. Anne, M. Z. Wrona, and D. Lemordant, J. Am. Chem. Soc., 1989, 111, 719. M. Z. Wrona, D. Lemordant, L. Lin, C. L. Blank, and G. Dryhurst, J. Med. Chem., 1986, 29, 499. A. K. Sinhababu and R. T. Borchardt, J. Am. Chem. Soc., 1985, 107, 7618.
21. Oxidation of some hydroxyindoles: A. Bertazzo, S. Catinella, and P. Traldi, J. Mass Spectrometry, 1996, 31, 735. A. Bertazzo, C. Costa, G. Allegri, D. Favretto, and P. Traldi, Rapid Commun. Mass Spectrometry, 1996, 10, 1299. T. Tabatabaie, R. N. Goyal, C. L. Blank and G. Dryhurst, J. Med. Chem., 1993, 36, 229. T. Tabatabaie and G. Dryhurst, J. Med. Chem., 1992, 35, 2261. T. Tabatabaie, M. Z. Wrona, and G. Dryhurst, J. Med. Chem., 1990, 33, 667. M. Z. Wrona and G. Dryhurst, J. Org. Chem., 1989, 54, 2718. G. Dryhurst, A. Anne, M. Z. Wrona, and D. Lemordant, J. Am. Chem. Soc., 1989, 111, 719. M. Z. Wrona, D. Lemordant, L. Lin, C. L. Blank, and G. Dryhurst, J. Med. Chem., 1986, 29, 499. A. K. Sinhababu and R. T. Borchardt, J. Am. Chem. Soc., 1985, 107, 7618.
22. Oxidation of some hydroxyindoles: A. Bertazzo, S. Catinella, and P. Traldi, J. Mass Spectrometry, 1996, 31, 735. A. Bertazzo, C. Costa, G. Allegri, D. Favretto, and P. Traldi, Rapid Commun. Mass Spectrometry, 1996, 10, 1299. T. Tabatabaie, R. N. Goyal, C. L. Blank and G. Dryhurst, J. Med. Chem., 1993, 36, 229. T. Tabatabaie and G. Dryhurst, J. Med. Chem., 1992, 35, 2261. T. Tabatabaie, M. Z. Wrona, and G. Dryhurst, J. Med. Chem., 1990, 33, 667. M. Z. Wrona and G. Dryhurst, J. Org. Chem., 1989, 54, 2718. G. Dryhurst, A. Anne, M. Z. Wrona, and D. Lemordant, J. Am. Chem. Soc., 1989, 111, 719. M. Z. Wrona, D. Lemordant, L. Lin, C. L. Blank, and G. Dryhurst, J. Med. Chem., 1986, 29, 499. A. K. Sinhababu and R. T. Borchardt, J. Am. Chem. Soc., 1985, 107, 7618.
23. Oxidation of some hydroxyindoles: A. Bertazzo, S. Catinella, and P. Traldi, J. Mass Spectrometry, 1996, 31, 735. A. Bertazzo, C. Costa, G. Allegri, D. Favretto, and P. Traldi, Rapid Commun. Mass Spectrometry, 1996, 10, 1299. T. Tabatabaie, R. N. Goyal, C. L. Blank and G. Dryhurst, J. Med. Chem., 1993, 36, 229. T. Tabatabaie and G. Dryhurst, J. Med. Chem., 1992, 35, 2261. T. Tabatabaie, M. Z. Wrona, and G. Dryhurst, J. Med. Chem., 1990, 33, 667. M. Z. Wrona and G. Dryhurst, J. Org. Chem., 1989, 54, 2718. G. Dryhurst, A. Anne, M. Z. Wrona, and D. Lemordant, J. Am. Chem. Soc., 1989, 111, 719. M. Z. Wrona, D. Lemordant, L. Lin, C. L. Blank, and G. Dryhurst, J. Med. Chem., 1986, 29, 499. A. K. Sinhababu and R. T. Borchardt, J. Am. Chem. Soc., 1985, 107, 7618.
24. Oxidation of some hydroxyindoles: A. Bertazzo, S. Catinella, and P. Traldi, J. Mass Spectrometry, 1996, 31, 735. A. Bertazzo, C. Costa, G. Allegri, D. Favretto, and P. Traldi, Rapid Commun. Mass Spectrometry, 1996, 10, 1299. T. Tabatabaie, R. N. Goyal, C. L. Blank and G. Dryhurst, J. Med. Chem., 1993, 36, 229. T. Tabatabaie and G. Dryhurst, J. Med. Chem., 1992, 35, 2261. T. Tabatabaie, M. Z. Wrona, and G. Dryhurst, J. Med. Chem., 1990, 33, 667. M. Z. Wrona and G. Dryhurst, J. Org. Chem., 1989, 54, 2718. G. Dryhurst, A. Anne, M. Z. Wrona, and D. Lemordant, J. Am. Chem. Soc., 1989, 111, 719. M. Z. Wrona, D. Lemordant, L. Lin, C. L. Blank, and G. Dryhurst, J. Med. Chem., 1986, 29, 499. A. K. Sinhababu and R. T. Borchardt, J. Am. Chem. Soc., 1985, 107, 7618.
25. Oxidation of some hydroxyindoles: A. Bertazzo, S. Catinella, and P. Traldi, J. Mass Spectrometry, 1996, 31, 735. A. Bertazzo, C. Costa, G. Allegri, D. Favretto, and P. Traldi, Rapid Commun. Mass Spectrometry, 1996, 10, 1299. T. Tabatabaie, R. N. Goyal, C. L. Blank and G. Dryhurst, J. Med. Chem., 1993, 36, 229. T. Tabatabaie and G. Dryhurst, J. Med. Chem., 1992, 35, 2261. T. Tabatabaie, M. Z. Wrona, and G. Dryhurst, J. Med. Chem., 1990, 33, 667. M. Z. Wrona and G. Dryhurst, J. Org. Chem., 1989, 54, 2718. G. Dryhurst, A. Anne, M. Z. Wrona, and D. Lemordant, J. Am. Chem. Soc., 1989, 111, 719. M. Z. Wrona, D. Lemordant, L. Lin, C. L. Blank, and G. Dryhurst, J. Med. Chem., 1986, 29, 499. A. K. Sinhababu and R. T. Borchardt, J. Am. Chem. Soc., 1985, 107, 7618.
26. Oxidation of some hydroxyindoles: A. Bertazzo, S. Catinella, and P. Traldi, J. Mass Spectrometry, 1996, 31, 735. A. Bertazzo, C. Costa, G. Allegri, D. Favretto, and P. Traldi, Rapid Commun. Mass Spectrometry, 1996, 10, 1299. T. Tabatabaie, R. N. Goyal, C. L. Blank and G. Dryhurst, J. Med. Chem., 1993, 36, 229. T. Tabatabaie and G. Dryhurst, J. Med. Chem., 1992, 35, 2261. T. Tabatabaie, M. Z. Wrona, and G. Dryhurst, J. Med. Chem., 1990, 33, 667. M. Z. Wrona and G. Dryhurst, J. Org. Chem., 1989, 54, 2718. G. Dryhurst, A. Anne, M. Z. Wrona, and D. Lemordant, J. Am. Chem. Soc., 1989, 111, 719. M. Z. Wrona, D. Lemordant, L. Lin, C. L. Blank, and G. Dryhurst, J. Med. Chem., 1986, 29, 499. A. K. Sinhababu and R. T. Borchardt, J. Am. Chem. Soc., 1985, 107, 7618.
27. Oxidation of some hydroxyindoles: A. Bertazzo, S. Catinella, and P. Traldi, J. Mass Spectrometry, 1996, 31, 735. A. Bertazzo, C. Costa, G. Allegri, D. Favretto, and P. Traldi, Rapid Commun. Mass Spectrometry, 1996, 10, 1299. T. Tabatabaie, R. N. Goyal, C. L. Blank and G. Dryhurst, J. Med. Chem., 1993, 36, 229. T. Tabatabaie and G. Dryhurst, J. Med. Chem., 1992, 35, 2261. T. Tabatabaie, M. Z. Wrona, and G. Dryhurst, J. Med. Chem., 1990, 33, 667. M. Z. Wrona and G. Dryhurst, J. Org. Chem., 1989, 54, 2718. G. Dryhurst, A. Anne, M. Z. Wrona, and D. Lemordant, J. Am. Chem. Soc., 1989, 111, 719. M. Z. Wrona, D. Lemordant, L. Lin, C. L. Blank, and G. Dryhurst, J. Med. Chem., 1986, 29, 499. A. K. Sinhababu and R. T. Borchardt, J. Am. Chem. Soc., 1985, 107, 7618.