13082-84-3

Basic information

• Product Name: 5,6-dimethyl-1-pentofuranosyl-1H-benzimidazole
• CAS NO: 13082-84-3
• Molecular Formula: C₁₄H₁₈N₂O₄
• Molecular Weight: 278.3037
• Mol File: 13082-84-3.mol

Chemical Properties

• Boiling Point: 569.2°C at 760 mmHg
• Flash Point: 298°C
• Density: 1.5g/cm³
• Vapor Pressure: 8.54E-14mmHg at 25°C
• Refractive Index: 1.683
• CAS DataBase Reference: 5,6-dimethyl-1-pentofuranosyl-1H-benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-dimethyl-1-pentofuranosyl-1H-benzimidazole(13082-84-3)
• EPA Substance Registry System: 5,6-dimethyl-1-pentofuranosyl-1H-benzimidazole(13082-84-3)

Safety Data

• Hazardous Substances Data: 13082-84-3(Hazardous Substances Data)

Upstream product

• 105499-44-3 2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride 
• 91275-64-8 5,6-dimethyl-1-(trimethylsilyl)-1H-benzimidazole 
• 54503-64-9 2,3-O-isopropylidene-5-O-trityl-D-ribofuranose 
• 84396-42-9 1-(5-O-triphenylmethyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-5,6-dimethylbenzimidazole 
• 582-60-5 5,6-dimethyl-1H-benzo[d]imida-zole 
• 118-00-3 G 
• 67525-66-0 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 

Relevant articles and documents

Benzimidazoles in the reaction of enzymatic transglycosylation

Substrate activity of a broad spectrum of derivatives of benzimidazole in the reaction of enzymatic ribo- and 2-deoxyribosylation catalyzed by purine nucleoside phosphorylase of whole cells of E. coli BMT-1D/1A has been studied Guanosine or 2'-deoxyguanosine were used as glycosyl donors.

Derivatives of 1-β-D-ribofuranosylbenzimidazole 3',5'-phosphate that mimic the actions of adenosine 3',5'-phosphate (cAMP) and guanosine 3',5'-phosphate (cGMP)

A series of new analogues of 1-β-D-ribofuranosylbenzimidazole 3',5'-phosphate (cBIMP) has been designed according to the properties predicted by the MNDO method, and synthesised from substituted benzimidazoles.Dipole vectors and HOMO and LUMO energies for each benzimidazole base were calculated by MNDO method and the lipophilicities of the cBIMP derivatives were determined.In general, the cBIMP derivatives activate cAMP-dependent protein kinases I and II and preferentially bind to site B, especially for the type II kinase, with 2-trifluoromethyl-cBIMP and 5,6-difluoro-cBIMP exhibiting the highest site selectivity.Each cBIMP derivative can stimulate cGMP-stimulated cyclic phosphodiesterase (cGS-PDE), with 5,6-dimethyl-cBIMP being as potent as cGMP, and also inhibit cGMP-inhibited phosphodiesterase (cGI-PDE).Only the 2-trifluoromethyl-cBIMP and the Rp-phosphorothioates (cBIMPS) (equatorial P=S) were resistant to hydrolysis by cPDE.The Sp-phosphorothioates were hydrolysed slowly, if at all.In addition to exhibiting a high lipophilicity, the most active compounds for the induction of apoptosis and inhibition of proliferation were also resistant to cPDE (Sp-5,6-dichloro-cBIMPS) and/or were potent activators of cAMP-dependent protein kinase (5,6-dichloro-cBIMP).

Deprotection of α-imidazole/benzimidazole ribonucleosides by catalytic carbon tetrabromide initiated photolysis

Several protected benzimidazole and imidazole α-ribonucleosides were deprotected in excellent yield at ambient temperature using CBr4 initiated photolysis in methanol at ambient temperature. No selectivity was observed and both trityl and isopr