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STRUCTURE ACTIVITY RELATIONSHIP OF IMIDAZO [1, 2-A] PYRIMIDINIUM SALTS AND SUBSTITUTED AMINO IMIDAZOLES AS INHIBITORS

    3 Author(s):  P.CHANTI BABU, R.S.K.SHARMA, B.JAYARAM

Vol -  4, Issue- 2 ,         Page(s) : 614 - 642  (2013 ) DOI : https://doi.org/10.32804/CASIRJ

Abstract

The class of 2-aminoimidazoles has recently been given particular interest due to various biological properties of these compounds. 2- Aminoimidazole alkaloids and their metabolites, isolated from the marine sponges Hymeniacidon sp., have been described as potent antagonists of serotonergic1 and histaminergic2 receptors. Naamine and isonaamine alkaloids from the marine sponges Leucetta sp. exhibit antiviral and anticancer activity.3, 4 Because of these interesting biological activities, numerous synthetic routes to 1-substituted and 1-unsubstituted 2- aminoimidazoles have been reported. Modern synthetic methods for accessing 1- unsubstituted 2-amino-1H-imidazoles can be roughly classified as heterocyclization of substituted or protected guanidines with 1,2-dielectrophiles, heteroaromatic nucleophilic substitution5c,6 and recyclization of 2-aminooxazoles.7 Although different 5a-c substituted guanidines are readily available and can be prepared in situ (e.g. from cyanamines8), the high basicity of guanidines together with non-regioselectivity often leads to multiple products.9Protection by acetyl5a and Boc-groups5c requires, in turn, acidic deprotection conditions. Another procedure is the cyclocondensation of aldehydes and guanidine nitrate using sodium cyanide and supported aluminum oxide, which provides symmetric 2-aminoimidazoles.10

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