Studies on alkylresorcinols and novel analogues

Abstract

Alkylresorcinols such as 1,3-dihydroxy-5-alkylbenzenes have been found to have a number of biological activites including antiparasitic, cytotoxic, fungicidal and bacteriocidal properties that act against various pathogens. These resorcinols have been found to be present and have been isolated from a range of plants in the Ancircardiaceae Ginkgoaceae and Graminae families. Alkylresorcinols have previously been synthesised by various routes, with the attachment of the side chain being the most challenging aspect of the synthesis. For comprehensive studies on their structure-activity relationships, an efficient synthetic route therefore needs to be found. Alkylresorcinols were to be used as standards in GC-MS and LC-MS based analytical methods for the detection and quantification of alkylresorcinols in human fluids. Carboxyalkylresorcinols were required for the development of new automated immunoassays of alkylresorcinols from biological samples. The work towards the synthesis of a number of novel analogues of resorcinol was achieved, namely 15-(3',5'-dihydroxyphenyl)pentadecane via a Suzuki coupling reaction; 16-(3',5'-dihydroxyphenyl)hexadecanoic acid via an iron(III) catalysed carbon-carbon coupling reaction employing a grignard reagent; 16-(3',5'-dihydroxyphenyl)hexadecane, 17-(3' ,5' -dihydroxyphenyl)heptadecanoic acid, 21 -(3',5'-dihydroxyphenyl)henicosanoic acid and 19-(3',5'-dihydroxyphenyl)nonadecanoic acid employing standard conditions of Wittig reactions.