Disulphonamides of aryl and aralkyl disubstituted amines and hydrazines

Abstract

The present thesis consists of four parts. They deal with the synthesis of the disulphonamides of diphenylamine, phenylbenzylamine, dibenzylamine, diphenylhydrazine and dibenzylhydrazine and their starting materials. Part I deals with the preparation of starting materials like diphenylamine and the sulphonyl chloride in improved yields. The synthesis of diphenylamine disulphonic acid has been for the first time carried out. It was obtained by the action of phosphorus pentachloride on diphenylamine sulphonic acid. Part II deals with the synthesis of disulphonamides of diphenylamine and its derivatives obtained by the action of various amines with diphenylamine-4,4'-disulphonyl chloride. It gives also an account of the experimental details. These disulphonamides of diphenylamine and its derivatives are expected to be active. The disulphonamide of diphenylhydrazine has also been synthesised with a view to studying its activity. Part III gives a detailed account of preparation of toluene sulphonyl chloride in yields. The bromination and the chlorination of the side chain of toluene have been fully examined and a better method for bromination and chlorination has been given. The synthesis of sulphonamides of bromo and chloro toluene sulphonyl chlorides is brought about by reacting the amines with the sulphonyl chlorides. The preparation of these amides for the first time undertaken by the author with a view to synthesise phenyl sulphonamide, 4-bromo sulphonamide and its derivatives. That the bromine and chlorine are formed during the halogenation or in other words the bromine and the chlorine have entered the side chain at toluene sulphonyl chloride is shown by the fact that on oxidation both the products give phenyl sulphonamide translatable to sulphone. Part IV gives the list of substituted 4-hydroxy sulphonamides and the method of their synthesis. The synthesis of the substituted 4-hydroxy sulphonamides was undertaken to find out any active compounds than the parent 4-hydroxy sulphonamide or sulphonamide itself. The carbonic anhydrase anti-oestatalam theory expects these compounds to be active. The synthesis of the disulphonamide of dibenzylhydrazine has also been done. The disulphonamide of diphenylglycine has also attracted the attention of the author as it has proved to be slightly water-soluble. In short, it can be said that the contents of this thesis is an attempt which has been made to improve the therapeutic potential and to decrease the toxic effects of sulphonamide and sulphanilamide. For this attempt, fourteen disulphonamides of diphenylamine, fourteen sulphonamides of alpha-bromo toluene sulphonic acid and the corresponding chloro toluene sulphonamides, fourteen sulphonamides of dibenzylamine and the disulphonamides of diphenylhydrazine and dibenzylhydrazine have been synthesised. Almost all the above compounds are characterised by low solubility with the result their long retention in the system is facilitated. They are being pharmacologically tested.