SYNTHESIS OF CERTAIN 1-POLY­ HYDROXYLATEDALKYL- β -CARBOLINE DERIVATIVES

Abstract

Numerous alkaloids of the IS-carboline-type with various substituents at C-1 are known to display various growth in­ hibitory activities such as: Oxopropalines, Pyridindolol, Lavendamycin, Manzamine C, and others. A new IS-carboline alkaloid (LXXXV) was isolated together

with other known indole alkaloids (LIXa & LIXb) from the fu­ sion cell suspension culture of Rauwolfia serpentina and Rhazya stricta (Family Apocyanaceae). The new alkaloid (LXXXV) (polyhydroxyalkyl)-IS-carboline skeleton. However, the full

structure elucidation of this alkaloid is not yet explored.

The presented thesis deals with the synthesis of some .derivatives of 1-(polyhydroxylatedalkyl)-IS-carbolines, basi­ cally related to compound (LXXXV), and preliminary screening of their potential activity as antiviral and I or cytotoxic agents. In part, it involves also structural elucidation of

the new alkaloid (LXXXV) as well as structural modification of its basic skeleton by introducing methyl and benzyl residues at N-9. Synthesis of the alkaloid (LIXa: R= COMe; Rl- R5= H) was

provided by reaction of 1-cyano-IS-carboline with methylmag­

nesium bromide under the conditions of Grignard reaction.

Alkaloid (LIXb: R= COOMe; R1- R5= H) was prepared through condensation of tryptamine and glyoxylic acid followed by esterification and dehydrogenation.