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A Frontier in Indole Chemistry: 1-Hydroxyindoles, 1-Hydroxytryptamines, and 1-Hydroxytryptophans

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Bioactive Heterocycles I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 6))

Abstract

Many new members of the 1-hydroxyindole, -tryptamine, and -tryptophan families are prepared. They demonstrate totally different reactivities from those of the corresponding indoles upon electrophilic substitution reactions. They also undergo nucleophilic substitution reactions that are unprecedented in indole chemistry. Doors to various kinds of new reactions and novel products open depending on the substrate structures and reaction conditions. 1-Hydroxyindoles, -tryptamines, and -tryptophans show a variety of biological activities, which makes this chemistry worth exploring for the development of new drugs.

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References

  1. 1-Hydroxyindole Hypotheses was first presented orally: Somei M, Karasawa Y, Tokutake S, Shoda S, Yamada F, Kaneko C (1980) 13th Congress of Heterocyclic Chemistry, Shizuoka, Japan. Abstracts Papers, p 33

    Google Scholar 

  2. Somei M, Kawasaki T, Fukui Y, Yamada F, Kobayashi T, Aoyama H, Shinmyo D (1992) Heterocycles 34:1877

    Google Scholar 

  3. Somei M, Fukui Y (1993) Heterocycles 36:1859

    CAS  Google Scholar 

  4. Hasegawa M, Tabata M, Satoh K, Yamada F, Somei M (1996) Heterocycles 43:2333

    CAS  Google Scholar 

  5. Somei M (1991) J Synth Org Chem 49:205

    CAS  Google Scholar 

  6. Somei M (1999) Heterocycles 50:1157

    CAS  Google Scholar 

  7. Somei M (2002) Recent Advances in the Chemistry of 1-Hydroxyindoles, 1-Hydroxytryptophans, and 1-Hydroxytryptamines. In: Katritzky AR (ed) Advances in Heterocyclic Chemistry, vol 82. Academic Press, London, 305 pp

    Google Scholar 

  8. Sundberg RJ (1970) The Chemistry of Indoles. Academic Press, New York; Sundberg RJ (1996) Indoles. Academic Press, New York

    Google Scholar 

  9. Somei M, Kawasaki T (1989) Heterocycles 29:1251

    CAS  Google Scholar 

  10. Yamada F, Kawanishi A, Tomita A, Somei M (2003) ARKIVOC viii:102

    Google Scholar 

  11. Yamada K, Tomioka S, Tanizawa N, Somei M (2004) Heterocycles 63:1601

    CAS  Google Scholar 

  12. Yamada K, Kawasaki T, Fujita T, Somei M (2001) Heterocycles 55:1151

    CAS  Google Scholar 

  13. Yamada K, Yamada F, Shiraishi T, Tomioka S, Somei M (2002) Heterocycles 58:53

    CAS  Google Scholar 

  14. Yamada F, Hayashi T, Yamada K, Somei M (2000) Heterocycles 53:1881

    CAS  Google Scholar 

  15. Nakai Y, Godou T, Yamada F, Somei M (2005) 125th Annual Meeting of Pharmaceutical Society of Japan, Tokyo, Japan. Abstract Papers, p 31

    Google Scholar 

  16. Lanzilotti AE, Littell R, Fanshawe WJ, McKenzie TC, Lovell FM (1979) J Org Chem 44:4809

    Article  CAS  Google Scholar 

  17. Hayashi T, Yamada F, Somei M (2002) 107th Meeting of Pharmaceutical Society of Japan, Hokuriku Branch, Fukui, Japan. Abstract Papers, p 18

    Google Scholar 

  18. Hasegawa M, Yamada K, Nagahama Y, Somei M (1999) Heterocycles 51:2815

    CAS  Google Scholar 

  19. Gribble GW, Hoffman JH (1977) Synthesis, p 859

    Google Scholar 

  20. Dinh TD, Vranken DLV (1999) J Peptide Res 53:465

    Article  CAS  Google Scholar 

  21. Yamada A, Fukui Y, Iwaki T, Ogasawara S, Okigawa M, Tanaka S, Somei M (2006) Heterocycles 67:129

    CAS  Google Scholar 

  22. Somei M, Kawasaki T, Shimizu K, Fukui Y, Ohta T (1991) Chem Pharm Bull 39:1905

    CAS  Google Scholar 

  23. Nakai Y, Goto A, Yamada F, Somei M (2003) Heterocycles 60:1589

    CAS  Google Scholar 

  24. Nakai Y, Asada M, Santo R, Hayashi T, Somei M (2004) 111st Meeting of Pharmaceutical Society of Japan, Hokuriku branch, Kanazawa, Japan. Abstract Papers, p 6

    Google Scholar 

  25. Hayashi T, Iwaki T, Yamada K, Somei M (2003) 33rd Congress of Heterocyclic Chemistry, Sapporo, Japan. Abstract Papers, p 60

    Google Scholar 

  26. Somei M, Fukui Y, Hasegawa M, Oshikiri N, Hayashi T (2000) Heterocycles 53:1725

    CAS  Google Scholar 

  27. Somei M, Tanimoto A, Orita H, Yamada F, Ohta T (2001) Heterocycles 54:425

    CAS  Google Scholar 

  28. Yamada K, Kanbayashi Y, Tomioka S, Somei M (2002) Heterocycles 57:1627

    CAS  Google Scholar 

  29. Nakatsuka S, Asano O, Ueda K, Goto T (1987) Heterocycles 26:1471

    CAS  Google Scholar 

  30. Iwaki T, Yamada F, Funaki S, Somei M (2005) Heterocycles 65:1811

    Article  CAS  Google Scholar 

  31. Yamada K, Izumi T, Yamada F, Somei M (2005) Heterocycles 66:583

    CAS  Google Scholar 

  32. Yamada F, Shinmyo D, Somei M (1994) Heterocycles 38:273

    CAS  Google Scholar 

  33. Nakai Y, Hayashi T, Yamada F, Somei M (2004) 34th Congress of Heterocyclic Chemistry. Kanazawa, Japan. Abstract Papers, p 253

    Google Scholar 

  34. Tomioka S, Yamada K, Yamada F, Tanizawa N, Shiraishi K, Somei (2003) 29th Symposium on Progress in Organic Reactions and Syntheses, Gifu, Japan. Abstracts, p 136

    Google Scholar 

  35. Reichardt C (1979) Solvent Effects in Organic Chemistry. Verlag Chemie GmbH, Weinheim

    Google Scholar 

  36. Yamada K, Yamada F, Somei M (2002) Heterocycles 57:1231

    CAS  Google Scholar 

  37. Yamada F, Goto A, Peng W, Hayashi T, Saga Y, Somei M (2003) Heterocycles 61:163

    CAS  Google Scholar 

  38. Hayashi T, Peng W, Nakai Y, Yamada K, Somei M (2002) Heterocycles 57:421

    CAS  Google Scholar 

  39. Nakai Y, Imai K, Tokumura K, Yamada F, Somei M (2005) 35th Congress of Heterocyclic Chemistry, Osaka, Japan. Abstract Papers, p 163

    Google Scholar 

  40. Hayashi T, Nakai Y, Yamada F, Somei M (2004) Heterocycles 62:437

    Article  CAS  Google Scholar 

  41. Somei M, Imai K, Yamada F, Hayashi T, Nakai Y, Tokumura K (2004) 34th Congress of Heterocyclic Chemistry, Kanazawa, Japan. Abstract Papers, p 255

    Google Scholar 

  42. Acheson RM, Benn MH, Jacyno J, Wallis JD (1983) J Chem Soc Perkin Trans 2:497

    Google Scholar 

  43. Somei M (1996) JP Patent 157475 [(1996) Chem Abstr 125:195426y]

    Google Scholar 

  44. Somei M (1991) JP Patent 31257 [(1991) Chem Abstr 114:247138a]

    Google Scholar 

  45. Muramatsu I (1996) Nihon Yakuzaishikai Zasshi 48:1987

    CAS  Google Scholar 

  46. Somei M, Shigenobu H, Tanaka Y JP Patent 2004-280104, applied Sept. 2004

    Google Scholar 

  47. Somei M, Shigenobu H (2001) JP Patent 2001-255963 [(2002) Chem Abstr 137:217126c]

    Google Scholar 

  48. Suzuki N, Hattori A (2002) J Pineal Res 33:253

    Article  CAS  Google Scholar 

  49. Suzuki N, Hattori A (2003) Life Sciences 73:2237

    Article  CAS  Google Scholar 

  50. Somei M, Hattori A, Suzuki N JP Patent 2004-64408, applied March 2004

    Google Scholar 

  51. Somei M, Hattori A, Suzuki N JP Patent 2005-209753, applied July 2005

    Google Scholar 

  52. Somei M, Ohnishi H, Shoken Y (1986) Chem Pharm Bull 34:677

    CAS  Google Scholar 

  53. Takasugi M, Monde K, Katsui N, Shirota A (1987) The 29th Symposium on The Chemistry of Natural Products, Sapporo, Japan. Symposium Papers, p 629

    Google Scholar 

  54. Pappolla M, Bozner P, Soto C, Shao H, Robakis NK, Zagorski M, Frangione B, Ghiso J (1998) J Biol Chem 273:7185

    Article  CAS  Google Scholar 

  55. Loeffler M (1996) Exp Clin Endocrinol Diabetes 104:308

    Article  CAS  Google Scholar 

  56. Ying SW, Niles LP, Crocker C (1993) Eur J Pharmacol Mol Pharmacol Sect 246:89

    Article  CAS  Google Scholar 

  57. Schmid H (1993) Gerontology 39:189

    Article  CAS  Google Scholar 

  58. Waldhauser F, Ehrart B, Forster E (1993) Experientia 49:671

    Article  CAS  Google Scholar 

  59. Pierpaoli W (1991) Aging 3:9

    Google Scholar 

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Acknowledgments

I am deeply grateful to a number of graduate students and undergraduates for their hard work and dedication. For biological evaluations, I also express cordial gratitude to Dr. Suzuki N (Noto Marine Lab., Kanazawa Univ.), Prof. Hattori A (Tokyo Medical and Dental Univ.), Prof. Shigenobu H, Assoc. Prof. Tanaka Y (Toho Univ.), Dr. Ekimoto H (Nippon Kayaku), and Dr. Kamuro Y (Nissan Chemical Ind. Ltd.).

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Correspondence to Masanori Somei .

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Shoji Eguchi

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Somei, M. A Frontier in Indole Chemistry: 1-Hydroxyindoles, 1-Hydroxytryptamines, and 1-Hydroxytryptophans. In: Eguchi, S. (eds) Bioactive Heterocycles I. Topics in Heterocyclic Chemistry, vol 6. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_037

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