94619-73-5

Basic information

• Product Name: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole
• Synonyms: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole
• CAS NO: 94619-73-5
• Molecular Weight: 562.538
• Mol File: 94619-73-5.mol

Chemical Properties

• CAS DataBase Reference: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole(94619-73-5)
• EPA Substance Registry System: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole(94619-73-5)

Safety Data

• Hazardous Substances Data: 94619-73-5(Hazardous Substances Data)

Upstream product

• 94619-75-7 N-formyl-N'-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)diaminomaleonitrile 
• 94619-71-3 N-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)diaminomaleonoitrile 
• 122-51-0 orthoformic acid triethyl ester 
• 1122-28-7 4,5-dicyano-1H-imidazole 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 53144-01-7 N-((Z)-2-amino-1,2-dicyanoethenyl)formamide 
• 94619-74-6 N-[(Z)-1,2-Dicyano-2-(trimethylsilanyl-amino)-vinyl]-formamide 
• 22224-38-0 1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose 

Downstream Products

• 2627-69-2 AICA riboside 
• 23192-64-5 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile 

Relevant articles and documents

Purine nucleoside analogues for treating flaviviridae including hepatitis C

This invention is directed to a method for treating a host, especially a human, infected with hepatitis C, flavivirus and/or pestivirus, comprising administering to that host an effective amount of an anti-HCV biologically active pentofuranonucleoside whe

Ring-expanded nucleosides and nucleotides

The present invention relates to compositions comprising analogues of purine nucleosides containing a ring-expanded (“fat”) heterocyclic ring, in place of purine, and an unmodified or modified sugar residue, pharmaceutically acceptable derivatives of such compositions, as well as methods of use thereof. In particular, these compositions may be utilized in the treatment of certain cancers, bacterial, fungal, parasitic, and viral infections, including, but not limited to, Acquired Immunodeficiency Syndrome (AIDS), hepatitis, Epstein-Barr and cytomegalovirus.

Ring-expanded nucleosides and nucleotides

The present invention relates to compositions comprising analogues of purine nucleotides containing a ring-expanded ("fat") heterocyclic ring, in place of purine, and an unmodified or modified sugar residue, pharmaceutically acceptable derivatives of such compositions, as well as methods of use thereof. In particular, these compositions may be utilized in the treatment of certain cancers, bacterial, fungal, parasitic and viral infections, including, but not limited to, Acquired Immunodeficiency Syndrome (AIDS) and hepatitis.

Ring-expanded nucleosides and nucleotides

The present invention relates to compositions comprising analogues of purine nucleosides containing a ring-expanded ("fat") heterocyclic ring, in place of purine, and an unmodified or modified sugar residue, pharmaceutically acceptable derivatives of such

A short synthesis of a novel ring-expanded purine and its nucleoside analogue containing the imidazo[4,5-e][1,3]diazepine ring skeleton with multiple amino substituents attached to the 7-membered ring

The synthesis of 4,6,8-triaminoimidazo[4,5-e][1,3]diazepine (1) and its nucleoside analogue (6) are reported. The heterocycle was prepared in a single step by condensation of 4,5-dicyanoimidazole with guanidine. The 5,7- fused ring structure of 1 was distinguished from the other possible 5:5- fused isomer 2 by preparing the 15N-labeled heterocycle (1*) and exploring its 15N-1H coupling patterns in both 1H and 15N NMR spectra. These spectral patterns also enabled establishment of the triamino tautomeric form of 1 as assigned. Compound 1, a novel ring-expanded ('fat') analogue of purine, is anticipated to be planar and aromatic as predicted by molecular modeling. The 1-benzyl analogue (4), a protocol for the ribosyl analogue 6, was similarly prepared from 1-benzyl-4,5-dicyanoimidazole. The nucleoside 6 was prepared by the modified Vorbruggen ribosylation of 1. The position of ribosylation was unequivocally established by an unambiguous synthesis of 6 from condensation of 1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4,5- dicyanoimidazole (7) with guanidine in a solution of sodium methoxide in methanol. The nucleoside 7 was prepared by the Vorbruggen ribosylation of 4,5-dicyanoimidazole.

Nucleosides from Carbohydrate Adducts of Diaminomaleonitrile. A Novel Synthesis of 5-Amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide and 5-Amino-1-(β-D-ribopyranosyl)imidazole-4-carboxamide

The stereospecific and regiospecific synthesis of 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (16) was achieved in six steps.A key intermediate in the synthesis, N-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)diaminomaleonitrile (3), was prepared by two routes: the reaction of diaminomaleonitrile (1) with 1-bromo-2,3,5-tri-O-benzoyl-β-D-ribofuranose (2) and the reaction of the bis(trimethylsilyl) derivative of diaminomaleonitrile (4) with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (5).Reaction of 3 triethyl orthoformate yielded 4,5-dicyano-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)imidazole (10).Alternatively 10 was synthesized by the acid-catalyzed cyclization of the N-formyl derivative 12 which was prepared by the reaction of the trimethylsilyl derivative of N-formyldiaminomaleonitrile 11 with 5.Deblocking 10 with 1 equiv of sodium methoxide at room temperature resulted in the regiospecific formation of the 5-imidate 14.Reaction of 14 with alkaline hypochlorite yielded 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carbonitrile (15) by a Hofmann rearrangement.Alkaline hydrolysis of the nitrile function yielded the corresponding amide 16. 5-Amino-1-(β-D-ribopyranosyl)imidazole-4-carboxamide (28) was prepared by a similar synthetic sequence.Reaction of diaminomaleonitrile (1) with ribose gave a mixture of the α- and β-anomers of D-ribopyranosyldiaminomaleonitrile (17).Compound 17 was converted to a mixture of the anomeric tri-O-acetates which on heating with triethyl orthoformate gave a separable mixture of the α- and β-anomers of 4,5-dicyano-1-(2',3',4'-tri-O-acetyl-D-ribopyranosyl)imidazole (19 and 20, respectively).Reaction of 19 with NH3/CH3OH at room temperature cleaved the three acetyl groups and regiospecifically converted the 5-cyano to the 5-imidate (26).The regiospecificity is due to the attack of the 2'-oxy anion on the 5-cyano group as shown by the isolation of the cyclic imidate 25 when the reaction is carried out at 0 deg C.The Hofmann rearrangement of imidate 26 followed by alkaline hydrolysis gave 5-amino-1-(β-D-ribopyranosyl)imidazole-4-carbonitrile 27 and 28, respectively.The 1H and 13C NMR spectra of imidates 14 and 26 have multiple peaks for the protons and carbons, respectively.Restricted rotation of the 5-imidate (energy of activation 18 kcal) results in isomers of 14 and 26 with different NMR spectra.The C-2, H-1' coupling constants of 2.5-3.1 Hz of the isomeric species comprising imidates 14 and 26 are consistent with a H-2, H-1' dihedral angle of 135 deg and an anti orientation of the imidazole with respect to the ribose ring; a conclusion confirmed by NOE measurements.