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Synthesis of 2-amino-s-triazino[1,2-a]benzimidazoles as potential antifolates from 2-guanidino- and 2-guanidino-5-methylbenzimidazoles

✍ Scribed by Anton V. Dolzhenko; Wai-Keung Chui

Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 90 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430115

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✦ Synopsis

Abstract

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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 ethoxymethylenemalonate 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 IC~50~ 10.9 μM.

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