PHOTOCHEMISTRY OF ANTIMALARIAL DRUGS.
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)
Document Details
- Document Type
- Technical Report
- Publication Date
- Mar 01, 1970
- Accession Number
- AD0710336
Entities
People
- Mordecai B. Rubin