1109266-74-1

Basic information

• Product Name: N-butyl-1,6-dideoxy-1,6-imino-D-mannitol
• CAS NO: 1109266-74-1
• Molecular Weight: 219.281
• Mol File: 1109266-74-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-butyl-1,6-dideoxy-1,6-imino-D-mannitol(CAS DataBase Reference)
• NIST Chemistry Reference: N-butyl-1,6-dideoxy-1,6-imino-D-mannitol(1109266-74-1)
• EPA Substance Registry System: N-butyl-1,6-dideoxy-1,6-imino-D-mannitol(1109266-74-1)

Safety Data

• Hazardous Substances Data: 1109266-74-1(Hazardous Substances Data)

Upstream product

• 109-73-9 N-butylamine 
• 19895-66-0 1,2:5,6-di-anhydro-D-mannitol 
• 69-65-8 mannitol 

Relevant articles and documents

Iminosugars: Effects of stereochemistry, ring size, and n-substituents on glucosidase activities

N-substituted iminosugar analogues are potent inhibitors of glucosidases and glycosyltransferases with broad therapeutic applications, such as treatment of diabetes and Gaucher disease, immunosuppressive activities, and antibacterial and antiviral effects against HIV, HPV, hepatitis C, bovine diarrhea (BVDV), Ebola (EBOV) and Marburg viruses (MARV), influenza, Zika, and dengue virus. Based on our previous work on functionalized isomeric 1,5-dideoxy-1,5-imino-D-gulitol (L-gulo-piperidines, with inverted configuration at C-2 and C-5 in respect to glucose or deoxynojirimycin (DNJ)) and 1,6-dideoxy-1,6-imino-D-mannitol (D-manno-azepane derivatives) cores N-linked to different sites of glucopyranose units, we continue our studies on these alternative iminosugars bearing simple N-alkyl chains instead of glucose to understand if these easily accessed scaffolds could preserve the inhibition profile of the corresponding glucose-based N-alkyl derivatives as DNJ cores found in miglustat and miglitol drugs. Thus, a small library of iminosugars (14 compounds) displaying different stereochemistry, ring size, and N-substitutions was successfully synthesized from a common precursor, D-mannitol, by utilizing an SN2 aminocyclization reaction via two isomeric bis-epoxides. The evaluation of the prospective inhibitors on glucosidases revealed that merely D-gluco-piperidine (miglitol, 41a) and L-ido-azepane (41b) DNJ-derivatives bearing the N-hydroxylethyl group showed inhibition towards α-glucosidase with IC50 41 μM and 138 μM, respectively, using DNJ as reference (IC50 134 μM). On the other hand, β-glucosidase inhibition was achieved for glucose-inverted configuration (C-2 and C-5) derivatives, as novel L-gulo-piperidine (27a) and D-manno-azepane (27b), preserving the N-butyl chain, with IC50 109 and 184 μM, respectively, comparable to miglustat with the same N-butyl substituent (40a, IC50 172 μM). Interestingly, the seven-membered ring L-ido-azepane (40b) displayed near twice the activity (IC50 80 μM) of the corresponding D-gluco-piperidine miglustat drug (40a). Furthermore, besides α-glucosidase inhibition, both miglitol (41a) and L-ido-azepane (41b) proved to be the strongest β-glucosidase inhibitors of the series with IC50 of 4 μM.