Accession Number : AD0710336

Title :   PHOTOCHEMISTRY OF ANTIMALARIAL DRUGS.

Descriptive Note : Final technical rept. 1 Oct 68-31 Dec 69,

Corporate Author : TECHNION RESEARCH AND DEVELOPMENT FOUNDATION LTD HAIFA (ISRAEL)

Personal Author(s) : Rubin,Mordecai B.

Report Date : MAR 1970

Pagination or Media Count : 18

Abstract : Photolysis of 2-phenyl-4-quinoline methanol in degassed methanol solution produces formaldehyde and 2-phenyl-4-methylquinoline in high yield. This reaction is inhibited by oxygen. Quinoline methanols of antimalarial interest, possessing nuclear chlorine substituents and 2-piperidyl or di-n-butylaminomethyl groups at the carbinol C-atom, react in a similar way to give formaldehyde and desoxy derivatives. In addition, some replacement of chlorine atoms also occurs. It is suggested that these reactions proceed via homolytic cleavage of the C-OH bond to give hydroxyl and 'benzylic' radicals. Abstraction of hydrogen from methanol by the benzylic radical and subsequent interaction of hydroxyl and hydroxymethyl radicals provides a reasonable explanation for the photochemical behaviour. Phototoxicity could be due to the intermediate radicals or to the stable products of reaction. Benzyl alcohol and 4-pyridine methanol did not react in analogous fashion. (Author)

Descriptors :   (*ANTIMALARIALS, *PHOTOCHEMICAL REACTIONS), PHOTOLYSIS, FREE RADICALS, IONS, TOXICITY, HALOGENATED HYDROCARBONS, CHLORINE COMPOUNDS, NITROGEN HETEROCYCLIC COMPOUNDS, ISRAEL

Subject Categories : Pharmacology
      Radiation and Nuclear Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE