Chemical confirmation of the structure of a mutagenic aminophenylnorharman, 9-(4'-aminophenyl)-9H-pyrido[3,4-b]indole: An authentic synthesis of 9-(4'nitrophenyl)-9H- pyrido[3,4-b]indole as its relay compound

Yasuoki Murakami, Nobuyuki Imai, Tsuyoshi Miura, Takashi Sugimura, Keiji Wakabayashi, Yukari Totsuka, Noriyasu Hada, Yuusaku Yokoyama, Hideharu Suzuki, Katsuyoshi Mitsunaga

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

9-(4'-Aminophenyl)-9H-pyrido[3,4-b]indole 2 is a mutagenic compound produced by non-mutagenic norharman 1 and aniline in the presence of S9 mix. 9-(4'-Nitrophenyl)-9H-pyrido[3,4-b]indole 4, the relay compound for synthesis of 2, was synthesized starting from ethyl indole-2-aldehyde 12 via initial N-(4-nitro)phenylation of the indole nucleus, elongation of the 2-aldehyde substituent, and then construction of the pyridine nucleus in order to ensure the nitrogen substitution in 2.

Original languageEnglish
Pages (from-to)455-462
Number of pages8
JournalHeterocycles
Volume80
Issue number1
DOIs
Publication statusPublished - 2010 Jan 1

Fingerprint

Carbolines
norharman
Aldehydes
Elongation
Substitution reactions
Nitrogen
4-nitrophenyl
9-(4'-aminophenyl)-9H-pyrido(3,4-b)indole
indole
aniline
pyridine

Keywords

  • 9H-Pyrido[3,4-b]indole
  • Cyclization
  • Indole Nucleus
  • Norharman
  • Synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Chemical confirmation of the structure of a mutagenic aminophenylnorharman, 9-(4'-aminophenyl)-9H-pyrido[3,4-b]indole : An authentic synthesis of 9-(4'nitrophenyl)-9H- pyrido[3,4-b]indole as its relay compound. / Murakami, Yasuoki; Imai, Nobuyuki; Miura, Tsuyoshi; Sugimura, Takashi; Wakabayashi, Keiji; Totsuka, Yukari; Hada, Noriyasu; Yokoyama, Yuusaku; Suzuki, Hideharu; Mitsunaga, Katsuyoshi.

In: Heterocycles, Vol. 80, No. 1, 01.01.2010, p. 455-462.

Research output: Contribution to journalArticle

Murakami, Yasuoki ; Imai, Nobuyuki ; Miura, Tsuyoshi ; Sugimura, Takashi ; Wakabayashi, Keiji ; Totsuka, Yukari ; Hada, Noriyasu ; Yokoyama, Yuusaku ; Suzuki, Hideharu ; Mitsunaga, Katsuyoshi. / Chemical confirmation of the structure of a mutagenic aminophenylnorharman, 9-(4'-aminophenyl)-9H-pyrido[3,4-b]indole : An authentic synthesis of 9-(4'nitrophenyl)-9H- pyrido[3,4-b]indole as its relay compound. In: Heterocycles. 2010 ; Vol. 80, No. 1. pp. 455-462.
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