1-Hydroxyindoles

Heterocycles

Volumn 50, Issue 2, 1999, Pages 1157-1211

  Somei, Masanori ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYINDOLE;

ACYLATION; ALKYLATION; CENTRAL NERVOUS SYSTEM; DERIVATIZATION; DRUG STABILITY; DRUG SYNTHESIS; MOLECULAR INTERACTION; REACTION ANALYSIS; REVIEW; THROMBOCYTE AGGREGATION;

EID: 0033117650     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-98-SR(H)8     Document Type: Review

References (128)

1. a) "1-Hydroxyindole Hypotheses" was first presented orally: M. Somei, Y. Karasawa, S. Tokutake, T. Shoda, F. Yamada, and C. Kaneko, Abstracts of Papers, The 13th Congress of Heterocyclic Chemistry, Shizuoka, Nov. 1980, p. 33;
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38. M. Somei, Unpublished data.
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59. M. Somei and T. Kobayashi, Heterocycles, 1992, 34, 1295.
60. M. Somei, H. Morikawa, K. Yamada, and F. Yamada, Heterocycles, 1998, 48, 1117.
61. a) M. Somei and A. Kodama, Heterocycles, 1992, 34, 1285;
62. b) K. Nakagawa and M. Somei, ibid., 1994, 39, 31.
63. M. Somei and M. Natsume, Tetrahedron Lett., 1973, 2451.
64. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
65. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
66. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
67. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
68. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
69. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
70. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
71. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
72. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
73. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
74. Nucleophilic substitution reactions were suggested in the following reports. R. J. Sundberg, J. Org. Chem., 1965, 30, 3604; J. Billet and S. G. Smith, Tetrahedron Lett., 1969, 4465; P. G. Gassman, G. A. Campbell, and G. Mehta, Tetrahedron, 1972, 28, 2749; T. Hino, M. Endo, M. Tonozuka, Y. Hashimoto, and M. Nakagawa, Chem. Pharm. Bull., 1977, 25, 2350; M. De. Rosa and J. L. T. Alonsa, J. Org. Chem., 1978, 43, 2639; D. V. C. Awang and A. Vincent, Can. J. Chem., 1980, 58, 1589; M. De. Rosa, L. Carbognani, and A. Febres, J. Org. Chem, 1981, 46, 2054; M. M. Cooper, G. J. Hignett, and J. A. Joule, J. Chem. Soc., Perkin Trans. 1, 1981, 3008; M. G. Beal, W. R. Ashcroft, M. M. Cooper, and J. A. Joule, ibid., 1982, 435; L. Dalton, G. L. Humphrey, M. M. Cooper, and J. A. Joule, ibid, 1983, 2417; J. Becher, P. L. Jørgensen, K. Pluta, N. J. Krake, and B. F. Hansen, J. Org. Chem., 1992, 57, 2127; P. H. H. Hermkens, R. Plate, C. G. Kruse, H. W. Scheeren, and H. C. J. Ottenheijm, ibid., 1992, 57, 3881.
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