Vincent C. Barry

Antituberculosis Activity in the Phenazine Series. Isomeric Pigments obtained by Oxidation of O- Phenylenediamine Derivatives.

INTRODUCTION THE products obtained on oxidation of derivatives of o-phenylenediamine with ferric chloride or p-benzoquinone have been under investigation in these laboratories for some years. The main products formed are derivatives of anilinoaposafranine (2-anilino-3 : 5-dihydro-3-imino-5phenylphenazine), I (R = Ph), and its isomer, 2-amino-3 : 5-dihydro-3phenylimino-5-phenylphenazine, I1 (R = Ph). R R

The reaction of the periodate-oxidation products of 1,4-anhydroerythritol and of some related pyrrolidine glycols with thiosemicarbazides

Abstract Simple analogues of the dialdehyde formed by periodate oxidation of benzyl β- L -arabinopyranoside have been prepared. Oxydiacetaldehyde may be condensed with one or two moles of substituted thiosemicarbazides, whereas N -aryliminodiacetaldehydes give only bis(thiosemicarbazones). The oxidation of N -arylpyrrolidine-3,4-diols with one equivalent of periodate is straightforward if electron-attracting aromatic substituents are present, but, otherwise, some cleavage of NC bonds in the pyrrolidine ring can be demonstrated. The crystalline hemialdal, 2,6-dihydroxy-4-phenylmorpholine, was isolated. The rates of conversion of some α-functionally-substituted thiosemicarbazones into glyoxal derivatives have been compared.

An organic chemist’s approach to the chemotherapy of tuberculosis

ConclusionThis is a record of some individual approaches to the problem of finding an adequate chemical agent for the treatment of tuberculosis. The syntheses of the branched-chain fatty compounds which have been described was inspired by the occurrence of branched fatty acids in the lipoid fractions of mycobacteria. Although these synthetic substances show considerable promise, it is not claimed that their activity is in any way related to the occurrence of branched fatty acids in the tubercle bacillus. It seems likely, however, that more knowledge of the chemistry and biochemistry of the bacillus will furnish fresh clues to guide synthetic work on similar lines. The activityin vivo of these basic fatty substances is of especial interest, as it provides some justification for the long preoccupation of workers in this field with compounds of a fatty character.As already described, the production of the active phenazine dyes was arrived at by a process of successive modifications of an antibiotic molecule (diploicin) which showed antituberculous activityin vitro. This is a game which anyone may play and the rules may be largely of his own devising. There can be no guarantee of success, but the probability of finding a synthetic chemotherapeutic agent for tuberculosis in this way should be no less than in a routine search for a natural antibiotic.