Synthesis of 5,6-substituted benzimidazoles and their evaluation as potential intermediates in the anaerobic vitamin B 12 biosynthesis pathway

Although benzimidazoles are well-recognized compounds in medicinal chemistry, they occur in the natural world primarily as lower ligands of Vitamin B and other cobamides. In this study, we present the synthesis of 5-methoxy-6-methylbenzimidazole and 5-hydroxy-6-methylbenzimidazole, and demonstrate t...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-11, Vol.60 (89), p.13012-13015
Main Authors: Vartak, Aniket S R, Verma, Shashank, Hazra, Amrita B
Format: Article
Language:English
Subjects:
Anaerobiosis
Benzimidazoles - chemical synthesis
Benzimidazoles - chemistry
Cobamides - chemistry
Cobamides - metabolism
Molecular Structure
Vitamin B 12 - analogs & derivatives
Vitamin B 12 - biosynthesis
Vitamin B 12 - chemistry
Vitamin B 12 - metabolism
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Summary:Although benzimidazoles are well-recognized compounds in medicinal chemistry, they occur in the natural world primarily as lower ligands of Vitamin B and other cobamides. In this study, we present the synthesis of 5-methoxy-6-methylbenzimidazole and 5-hydroxy-6-methylbenzimidazole, and demonstrate their ability to produce functional cobamides and N-1'-α-glycosidic-benzimidazolyl-ribosylphosphate isomers which are putative B biosynthesis intermediates.
ISSN:1359-7345
1364-548X
DOI:10.1039/D4CC04489D