118908-07-9

Basic information

• Product Name: 5-ethynyl-1-ribofuranosylimidazole-4-carboxamide
• Synonyms: 5-ethynyl-1-ribofuranosylimidazole-4-carboxamide
• CAS NO: 118908-07-9
• Molecular Formula: C11H13 N3 O5
• Molecular Weight: 267.24
• Mol File: 118908-07-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 686.3°Cat760mmHg
• Flash Point: 368.9°C
• Appearance: /
• Density: 1.67g/cm³
• Vapor Pressure: 8.86E-20mmHg at 25°C
• Refractive Index: 1.698
• CAS DataBase Reference: 5-ethynyl-1-ribofuranosylimidazole-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ethynyl-1-ribofuranosylimidazole-4-carboxamide(118908-07-9)
• EPA Substance Registry System: 5-ethynyl-1-ribofuranosylimidazole-4-carboxamide(118908-07-9)

Safety Data

• Hazardous Substances Data: 118908-07-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13N3O5/c1-2-5-7(10(12)18)13-4-14(5)11-9(17)8(16)6(3-15)19-11/h1,4,6,8-9,11,15-17H,3H2,(H2,12,18)/t6-,8-,9-,11-/m1/s1

Upstream product

• 126004-13-5 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carbonitrile 
• 23192-63-4 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 59354-00-6 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 118744-90-4 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-imidazole-4-carboxamide 
• 182494-76-4 5-Ethynyl-1-((3aR,4R,6S,6aS)-6-formyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-imidazole-4-carboxylic acid amide 
• 182494-73-1 5-ethynyl-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 182494-77-5 5-ethynyl-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 118908-01-3 5-<2-(trimethylsilyl)-1-ethyn-1-yl>-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 126004-21-5 5-<(trimethylsilyl)-1-ethyn-1-yl>-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 2627-69-2 AICA riboside 
• 23274-21-7 5-Amino-4-carbamoyl-1β-(2',3',5'-tri-O-acetyl-D-ribofuranosyl)imidazole 
• 182494-75-3 1-[(3aR,4R,6R,6aR)-6-(1,3-Diphenyl-imidazolidin-2-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-ethynyl-1H-imidazole-4-carboxylic acid amide 
• 182494-74-2 1-[(3aR,4R,6R,6aR)-6-(1,3-Diphenyl-imidazolidin-2-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-ethynyl-1H-imidazole-4-carbonitrile 
• 182494-72-0 Acetic acid (3aR,4R,6R,6aR)-6-(4-cyano-5-trimethylsilanylethynyl-imidazol-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 

Downstream Products

• 126004-16-8 5-ethynylimidazole-4-carboxamide 
• 56039-11-3 3-deazaguanosine 

Relevant articles and documents

Syntheses of [2-2H]-5-ethynyl-1-(β-D-ribofuranosyl) imidazole-4-carboxamide and 5-ethynyl-1-([5-3H]-β-D-ribofuranosyl)imidazole-4- carboxamide (EICAR)

Metallation of 5-ethynyl-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofura nosyl)imidazole -carboxamide (1) using n-BuLi, deuteration with deuterium oxide and removal of the tert-butyldimethylsilyl protecting groups using tetrabutylammonium fluroide yielded [2-2H]-5-ethynyl- 1-(β-D-ribofuranosyl)imidazole-4-carboxamide (5a, 75 atom % deuterium). Regiospecific deprotection of the masked aldehyde N,N'-diphenylethylenediamino synthon 14 using DIAION PK2I2 ion-exchange resin (H+ form) yielded the aldehyde derivative (15). Reduction of the aldehyde moiety of 15 using excess [3H]NaBH4 gave the carbinol product 17. Removal of the ribofuranosyl 2,3-isopropylidene protecting group from 17 using 90% trifluoroacetic acid afforded 5-ethynyl-1-([5-3H]-β-D-ribofuranosyl)imidazole-4-carboxamide (18. 19% chemical yield, > 99% radiochemical purity, specific activity 1.56 Ci/mmol).

Imidazole derivatives, process for production thereof, and use thereof

Disclosed are imidazole derivatives represented by formula [I]: STR1 wherein R is a hydrogen atom or STR2 wherein R2 is a hydrogen atom or a hydroxy protecting group, R2 protecting either a single hydroxy or two hydroxies together when R2 is a hydroxy protecting group, and R3 is a hydrogen atom or OR2 ; A is CONH2 or CN; and R1 is a hydrogen atom, lower alkyl, hydroxy lower alkyl, or phenyl. Also disclosed are six processes for producing these novel compounds among which a typical process comprises reacting a starting imidazole compound having a halogen at the 5-position thereof with an acetylene derivative to alkynylate the 5-position. Furthermore, the compounds having remarkable antitumor activities and therefore can provide novel antitumor agents.