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Chemotherapy of tuberculosis

Part IV. Synthesis of phthalyl andortho-toluoyl derivatives of the sulphonamides and sulphones as possible mycobacterial antagonists

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Summary

In order to fit the sulphonamides and sulphones out better for use in the chemotherapy of tuberculosis and leprosy, synthesis has been effected of a series ofo-phthalic ando-toluic acid derivatives of well-known sulphonamides and disubstituted diphenyl sulphones as possible mycobacterial antagonists.

Phthalic ando-toluic acid derivatives were chosen for synthesis in view of the recent theory advanced by Shemiakin that the antihæmorrhagic activity of substances of a vitamin K nature, intimately connected with the metabolism of mycobacteria, is due to phthalic acid which arises from the antihæmorrhagic substances. The study of the compounds designed as possible mycobacterial antagonists is expected to shed additional light on the mode of action of antihæmorrhagic compounds and the relation between antihæmorrhagic action and antimycobacterial efficacy.

The twenty-six compounds synthesised includeo-phthalic acid derivatives of sulphanilamidopyrimidine, sulphanilamido-4-methyl, and sulphanilamido-4: 6-dimethyl pyrimidines and of 4-nitro-, 4-acetamido-diphenyl-sulphones and 4∶4′-diaminodiphenyl sulphone. They also include N4-o-toluoyl derivatives of sulphanilamide, sulphathizoale, sulphathiazoline, sulphapyridine, sulphadiazine, sulphamerazine, 5-bromo-sulphadiazine, and 5-bromosulphamerazine. Other toluic acid derivatives prepared are N4, N1-di-o-toluoyl sulphanilamide, 4∶4′-o-ditoluoylamido-diphenyl sulphone and 4-nitro- and 4-amino-4′-o-toluoylamido-diphenyl sulphones. In addition, N1-o-toluoyl derivatives have been obtained from N4-formyl-, N4-acetyl-, N4-n-butyryl-, N4-n-valeryl-, N4-n-caproyl-, N4-p-heptoyl-, N4-cyclohexoyl and N4-cinnamoyl-sulphanilamides.

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Authors and Affiliations

  1. Department of Chemotherapy, Haffkine Institute, Bombay

    C. V. Deliwala & S. Rajagopalan

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  1. C. V. Deliwala
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  2. S. Rajagopalan
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(Communicated by Major-General Sir S. S. Sokhey,kt., f.a.sc.)

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Deliwala, C.V., Rajagopalan, S. Chemotherapy of tuberculosis. Proc. Indian Acad. Sci. (Math. Sci.) 31, 117–123 (1950). https://doi.org/10.1007/BF03047008

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