1,5-dimethyl-6H-pyridazino[4,5-b]carbazole, a 3-aza bioisoster of the antitumor alkaloid olivacine

Chem Pharm Bull (Tokyo). 2002 Nov;50(11):1479-83. doi: 10.1248/cpb.50.1479.

Abstract

A series of b-fused carbazoles structurally related to pyrido[4,3-b]carbazole-type alkaloids was prepared, utilizing the Diels-Alder reaction of 1-methylpyrano[3,4-b]indol-3(9H)-one with electron-deficient acetylenic dienophiles as the key step. The title compound (14) thus obtained in only four steps represents a new 3-aza analog of the antitumor natural product, olivacine.

MeSH terms

  • Alkaloids / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Carbazoles / chemistry*
  • Ellipticines / chemistry*
  • Pyridazines / chemistry*

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Carbazoles
  • Ellipticines
  • Pyridazines
  • olivacine