5,6-Dimethylbenzimidazole
Chemical compound
From Wikipedia, the free encyclopedia
5,6-Dimethylbenzimidazole (DMB) is a naturally occurring derivative of benzimidazole with two methyl groups as substituents on the benzene ring.
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| Names | |
|---|---|
| Preferred IUPAC name
5,6-Dimethyl-1H-1,3-benzimidazole | |
| Identifiers | |
3D model (JSmol) |
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| 116595 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.008.627 |
| EC Number |
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| 279255 | |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C9H10N2 | |
| Molar mass | 146.193 g·mol−1 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302, H315, H319, H335, H412 | |
| P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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5,6-Dimethylbenzimidazole is biosynthesized from flavin mononucleotide by the enzyme 5,6-dimethylbenzimidazole synthase.[1]
Occurrence and uses
Biological significance
5,6-Dimethylbenzimidazole is a substructure of true vitamin B12, where it serves as one of the ligands for the cobalt atom. In part of one of the pathways for cobalamin biosynthesis, DMB is a substrate for nicotinate-nucleotide—dimethylbenzimidazole phosphoribosyltransferase. One form of pseudovitamin B12, i.e. a compound usable by B12-dependent lactic acid bacteria but not by humans, has this group replaced with adenyl.[2] Despite production of pseudo B12 in groups as distantly related as lactic acid bacteria and Cyanobacteria, DMB is preferred over adenine by the vast majority of versions of CobT, the enzyme responsible for making the active phosphoribosylated "lower group" of cobalamin.[3]
Medicinal chemistry
Researchers have explored the pharmacological properties of benzimidazole derivatives, with some displaying antimicrobial, antiviral, anticancer, and antifungal activities.[4] The specific medicinal properties of 5,6-dimethylbenzimidazole may vary based on its structural features and substituents.[5]