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Title: Studies in structure and amoebicidal activity
Author: Mahboob, Sardar
Awarding Body: University of London
Current Institution: Royal Holloway, University of London
Date of Award: 1950
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The aim of the present investigation was to obtain more information as to the relation between structure and amoebicidal activity in the aliphatic diamines. Trimethylenediamine was prepared from glutaric acid by Schmidt's reaction. Tetramethylenediamine was obtained by doing Hoftmann's reaction on adipamide. Both the diamines were found to have no amoebicidal activity in vitro. An attempt was made to prepare 1:3-diamino-1:3-di-iso-amylpropane from 1:3-di-iso-amylglutaric acid by Schmidt's reaction but an unsaturated base was obtained. 1:3-Di-iso-amylglutaric acid was obtained from the decarboxylation of 1:3-di-iso-amylpropane 1:1;3:3-tetra-carboxylic acid, which was prepared by the hydrolysis of ethyl 1:3-di-iso-amylpropane-3:3-tetracarboxylate, the latter being obtained by treating ethyl propane-1:1:3:3-tetracarboxylate with iso-amyl bromide in presence of sodium ethoxide in alcohol.16 Diamines of the general formula (a) were prepared from 1:4-dialkyladipic acids, 1:5-dialkylpimelic acids,where n = 2, 3, 4 and 5, R = any one of the following: n-butyl, iso-butyl, n-amyl, iso-amyl, n-hexyl and 2-ethylhexyl.(a)1:6-dialkylsuberie acids, 1:7-dialkylazelaic acids which were obtained by the decarboxylation of 1:4-dialkylbutane-1;1;4;4-tetracarboxylic acids, 1:5-dialkylpentane-1:1:5:5-tetracarboxylic acids, 1:6-dialkylhexane-1:1:6:6-tetra-carboxylic acids and 1:7-dialkylheptane-1:1:7:7-tetracarboxylic acids. The above tetracarboxylic acids were prepared in the following way. Diethyl alkylmalonates were treated with sodium ethoxide in absolute alcohol and then with ethylene dibromide, trimethylene dibromide, tetramethylene dibromide and pentamethylene dibromide. The resulting dialkylbutane, pentane, hexane and heptane -tetracarboxylates were purified and hydrolysed to theircorresponding tetracarboxylic acids. Amoebicidal activity of these diamines increases withincreasing molecular weight and the increasing number of carbon atoms between the two amino groups the optimum number being five. Diamines containing branched carbon chain are less active than the straight chain diamines of the same molecular weight.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic Chemistry