864155-85-1

Basic information

• Product Name: 4-chloro-2-fluoro-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine
• Synonyms: 4-chloro-2-fluoro-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine
• CAS NO: 864155-85-1
• Molecular Weight: 616.002
• Mol File: 864155-85-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-chloro-2-fluoro-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-2-fluoro-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine(864155-85-1)
• EPA Substance Registry System: 4-chloro-2-fluoro-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine(864155-85-1)

Safety Data

• Hazardous Substances Data: 864155-85-1(Hazardous Substances Data)

Upstream product

• 224946-82-1 2-amino-3-benzyl-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 864155-80-6 2-amino-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one 
• 864155-79-3 2-amino-3-benzyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one 
• 864155-81-7 2-amino-4-chloro-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine 

Downstream Products

• 864155-93-1 4-chloro-2-fluoro-5-benzyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidine 

Relevant articles and documents

Synthesis and biological evaluation of 2- and 7-substituted 9-deazaadenosine analogues

A series of 2-halogen and 7-alkyl substituted analogues of 9-deazaadenosine and 2′-deoxy-9-deazaadenosine was synthesized by new efficient methodology involving transformation of corresponding 9-deazaguanosine and 2′-deoxyguanosine, which in turn were synthesized by direct C-glycosylation of 1-benzyl-9-deazaguanine with 1-O-acetyl-2,3,5-tri-O-benzoyl- D-ribofuranose and methyl 2-deoxy-3,5-di-O-(p-toluoyl)-D-ribofuranoside, respectively. Deoxychlorination of C6 and diazotization/chloro-or fluoro-dediazoniation of the sugar-protected 9-deazaguanosine, followed by selective ammonolysis at C6 and deprotection of the sugar moiety, gave 2-chloro- and 2-fluoro-9-deazaadenosine (6 and 9). Substitution of the 7-position of the dihalogen-intermediate with alkyl groups, followed by ammonolysis and deprotection, provided 2-chloro-7-alkyl-9-deazaadenosines (13a-e) and 2-fluoro-7-benzyl-9-deazaadenosine (13f). Catalytic hydrogenation of 13a-e gave 7-alkyl-9-deazaadenosines 14a-e. Similarly, 2-chloro-2′-deoxy-9- deazaadenosine (21), 2-chloro-2′-deoxy-7-methyl-9-deazaadenosine (25), 2′-deoxy-9-deazaadenosine (22), and 2′-deoxy-7-methyl-9- deazaadenosine (26) were prepared from sugar-protected 2′-deoxy-9- deazaguanosine. Among these compounds, 7-benzyl-9-deazaadenosine (14b) showed the most potent cytotoxic activity, with IC50 values of 0.07, 0.1, 0.2 and 1.5 μM, while both 7-methyl-9-deazaadenosine (14a) and 2-fluoro-9-deazaadenosine (9) also demonstrated significant cytotoxic activity with IC50 values of 0.4, 0.7, 0.3, and 1.5 μM, and 1.5, 0.9, 0.3, and 5 μM against L1210 leukemia, P388 leukemia, CCRF-CEM lymphoblastic leukemia, and B16F10 melanoma cells, respectively.