Studies in structure and amoebicidal activity

Mahboob, Sardar

(1950)

Mahboob, Sardar (1950) Studies in structure and amoebicidal activity.

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Abstract

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.

Information about this Version

This is a Accepted version
This version's date is: 1950
This item is not peer reviewed

Link to this Version

https://repository.royalholloway.ac.uk/items/9727d21f-3305-429c-ad94-bdd062b83b12/1/

Item TypeThesis (Doctoral)
TitleStudies in structure and amoebicidal activity
AuthorsMahboob, Sardar
Uncontrolled KeywordsOrganic Chemistry; Pure Sciences; Activity; Amoebicidal; Diamines; Diamines; Structure; Studies
Departments

Identifiers

ISBN978-1-339-62025-1

Deposited by () on 31-Jan-2017 in Royal Holloway Research Online.Last modified on 31-Jan-2017

Notes

Digitised in partnership with ProQuest, 2015-2016. Institution: University of London, Bedford College (United Kingdom).


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