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

  • Masanori SomeiEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (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.

Indole Electrophilic substitution Nucleophilic substitution DFT calculations Biologically active compound 

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Notes

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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Authors and Affiliations

  1. 1.Division of Pharmaceutical Sciences, Graduate School of Natural Science and TechnologyKanazawa UniversityKanazawaJapan

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