ChemInform Abstract: Cancerostatics. Part 6. Synthesis and Antineoplastic Properties of Some Benzoiso-α-carbolines.
Abstract
2-Halopyridine derivatives such as the quinolines (I) are coupled with the benzotriazoles (II) to yield the intermediates (III) which release nitrogen upon heating in polyphosphoric acid, forming the fused α-carbolines (IV).
ChemInform Abstract
2-Halopyridine derivatives such as the quinolines (I) are coupled with the benzotriazoles (II) to yield the intermediates (III) which release nitrogen upon heating in polyphosphoric acid, forming the fused α-carbolines (IV). Subsequent methylation takes place at the pyridine nitrogen, producing the benzoiso-α-carbolines (VI). An alternative pathway to the α-carboline moiety consists in the reaction of the 2-chloro-3-nitropyridines (VIII) with α-naphthylamine (VII), followed by consecutive reduction and diazotization to give the pyridotriazoles (XII). These are denitrogenated and rearranged and subsequently N-methylated, yielding the iso-α-carbolines (XIV). The analogue (XV) is similarly obtained from (VIIIb) and β-naphthylamine. The derivative (VIb) shows antitumor activity against leukemias P388 and L1210 and melanoma B16.
