Please use this identifier to cite or link to this item: https://doi.org/10.1002/jhet.5570430115
Title: Synthesis of 2-amino-s-triazino[1,2-a]benzimidazoles as potential antifolates from 2-guanidino- and 2-guanidino-5-methylbenzimidazoles
Authors: Dolzhenko, A.V. 
Chui, W.-K. 
Issue Date: Jan-2006
Citation: Dolzhenko, A.V., Chui, W.-K. (2006-01). Synthesis of 2-amino-s-triazino[1,2-a]benzimidazoles as potential antifolates from 2-guanidino- and 2-guanidino-5-methylbenzimidazoles. Journal of Heterocyclic Chemistry 43 (1) : 95-100. ScholarBank@NUS Repository. https://doi.org/10.1002/jhet.5570430115
Abstract: The syntheses of 2-amino-s-triazino[1,2-a]benzimidazoles from 2-guanidinobenzimidazoles were successfully carried out by a ring annelation reaction. The regiochemistry of the ring closure of 5-methyl-2- guanidinobenzimidazole with diethyl azodicarboxylate, aldehydes, acetone, diethyl ethoxymethylene-malonate and orthoesters, leading to the formation of s-triazine ring was studied. High regioselectivity was not observed in any of these reactions. However, the synthesis of s-triazino[1,2-a]benzimidazole system was found to be more regioselective than its 3,4-dihydro analogue. NOESY experiment indicated that the compound, 2-amino-4,4-dimethyl-3,4-dihydro-s- triazino[1,2-a]benzimidazole existed predominantly as the 3,4-dihydro tautomer in dimethyl sulfoxide. It was found to inhibit bovine dihydrofolate reductase with IC50 10.9 μM.
Source Title: Journal of Heterocyclic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/106401
ISSN: 0022152X
DOI: 10.1002/jhet.5570430115
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