1440537-03-0

Basic information

• Product Name: 4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl]-5-iodopyrrolo[2,3-d]pyrimidine
• CAS NO: 1440537-03-0
• Molecular Weight: 639.781
• Mol File: 1440537-03-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl]-5-iodopyrrolo[2,3-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl]-5-iodopyrrolo[2,3-d]pyrimidine(1440537-03-0)
• EPA Substance Registry System: 4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl]-5-iodopyrrolo[2,3-d]pyrimidine(1440537-03-0)

Safety Data

• Hazardous Substances Data: 1440537-03-0(Hazardous Substances Data)

Upstream product

• 123148-78-7 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 134877-42-2 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose 

Downstream Products

• 1440537-19-8 4-amino-7-[2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl]-5-phenylpyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

Synthesis and Cytostatic and Antiviral Activities of 2′-Deoxy-2′,2′-difluororibo- and 2′-Deoxy-2′-fluororibonucleosides Derived from 7-(Het)aryl-7-deazaadenines

A series of sugar-modified derivatives of cytostatic 7-heteroaryl-7-deazaadenosines (2′-deoxy-2′-fluororibo- and 2′-deoxy-2′,2′-difluororibonucleosides) bearing an aryl or heteroaryl group at position7 was prepared and screened for biological activity. The difluororibonucleosides were prepared by non- stereoselective glycosidation of 6-chloro-7-deazapurine with benzoyl-protected 2-deoxy-2,2-difluoro-D-erythro-pentofuranosyl-1-mesylate, followed by amination and aqueous Suzuki cross-couplings with (het)arylboronic acids. The fluororibo derivatives were prepared by aqueous palladium-catalyzed cross-coupling reactions of the corresponding 7-iodo-7-deazaadenine 2′-deoxy-2′-fluororibonucleoside 20 with (het)arylboronic acids. The key intermediate 20 was prepared by a six-step sequence from the corresponding arabinonucleoside by selective protection of 3′- and 5′-hydroxy groups with acid-labile groups, followed by stereoselective SN2 fluorination and deprotection. Some of the title nucleosides and 7-iodo-7-deazaadenine intermediates showed micromolar cytostatic or anti-HCV activity. The most active were 7-iodo and 7-ethynyl derivatives. The corresponding 2′-deoxy-2′,2′-difluororibonucleoside 5′-O-triphosphates were found to be good substrates for bacterial DNA polymerases, but are inhibitors of human polymeraseα. Sugar modified: Fluorinated analogues of 7-(het)aryl-7-deazaadenines were synthesized, and these nucleosides showed micromolar cytostatic activity against cancer cell lines and moderate anti-HCV activity. The corresponding nucleoside 5′-O-triphosphates were found to be good substrates for bacterial DNA polymerases, but are inhibitors of human polymeraseα.