476468-47-0

Basic information

• Product Name: 8-(2'-deoxy-β-D-ribofuranosyl)-2-methyl-4-(N-methyl-N-phenylamino)pyrazolo[1,5-a]-1,3,5-triazine
• Synonyms: 8-(2'-deoxy-β-D-ribofuranosyl)-2-methyl-4-(N-methyl-N-phenylamino)pyrazolo[1,5-a]-1,3,5-triazine
• CAS NO: 476468-47-0
• Molecular Weight: 355.396
• Mol File: 476468-47-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 8-(2'-deoxy-β-D-ribofuranosyl)-2-methyl-4-(N-methyl-N-phenylamino)pyrazolo[1,5-a]-1,3,5-triazine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-(2'-deoxy-β-D-ribofuranosyl)-2-methyl-4-(N-methyl-N-phenylamino)pyrazolo[1,5-a]-1,3,5-triazine(476468-47-0)
• EPA Substance Registry System: 8-(2'-deoxy-β-D-ribofuranosyl)-2-methyl-4-(N-methyl-N-phenylamino)pyrazolo[1,5-a]-1,3,5-triazine(476468-47-0)

Safety Data

• Hazardous Substances Data: 476468-47-0(Hazardous Substances Data)

Upstream product

• 55457-17-5 2-methylpyrazolo<1,5-a>-s-triazin-4-one 
• 476468-45-8 8-iodo-2-methyl-4-(N-methyl-N-phenylamino)pyrazolo[1,5-a]-1,3,5-triazin-4-one 
• 476468-38-9 2-methyl-4-(N-methyl-N-phenylamino)pyrazolo[1,5-a]-1,3,5-triazin-4-one 
• 476468-37-8 4-chloro-2-methylpyrazolo[1,5-a][1,3,5]triazine 
• 121-69-7 N,N-dimethyl-aniline 
• 96761-00-1 1,4-anhydro-2-deoxy-D-erythro-pent-1-enitol 
• 476468-46-9 2-methyl-4-(N-methyl-N-phenylamino)-8-(β-D-glycero-pentofuran-3'-ulose-1'-yl)pyrazolo[1,5-a]-1,3,5-triazine 

Downstream Products

• 476468-49-2 8-(2'-deoxy-β-D-ribofuranosyl)-2-methyl-4-(N-methylamino)pyrazolo[1,5-a]-1,3,5-triazine 3',5'-bis(dibenzyl phosphate) 

Relevant articles and documents

A general approach toward the synthesis of C-nucleoside pyrazolo[1,5-a]-1,3,5-triazines and their 3',5'-bisphosphate C-nucleotide analogues as the first reported in vivo stable P2Y(1)-receptor antagonists.

In our effort to identify potent purinergic P2Y(1) receptor antagonists as potent platelet aggregation inhibitors with enhanced metabolic stability, we developed an efficient route for the large-scale preparation of 2'-deoxy-C-nucleosides of pyrazolo[1,5-a]-1,3,5-triazine. The key strategic elements of this novel synthetic approach involved the following: (i) the use of a novel activating group, the N-methyl-N-phenylamino group, which was easily generated in high yield by treatment of the pyrazolo[1,5-a]-1,3,5-triazin-4-one (5) with phosphorus oxychloride and dimethylaniline under high pressure, (ii) a regio- and stereospecific palladium-mediated coupling reaction of the readily available unprotected glycal 1,4-anhydro-2-deoxy-D-erythro-pent-1-enitol (4b) and the 8-iodo derivative (16), and (iii) the stereoselective reduction of the ketone group of the furanosyl ring followed by the subsequent displacement of the N-methyl-N-phenylamino group upon treatment with methylamine. The beta configuration at the anomeric C-1' position of the glycal moieties was perfectly retained throughout this conversion. This procedure afforded 8-(2'-deoxy-beta-D-ribofuranosyl)-2-methyl-4-(N-methylamino)pyrazolo[1,5-a]-1,3,5-triazine (21) and 8-(2'-deoxy-beta-D-xylofuranosyl)-2-methyl-4-(N-methylamino)pyrazolo[1,5-a]-1,3,5-triazine (24) with an overall yield of 50% and 39%, respectively. Finally, the conversion of nucleosides 21 and 24 to the pyrazolotriazine C-nucleotides 3',5'-bisphosphate 2 and 3',5'-cyclophosphate 26 is also described herein and represents the first reported nucleotide derivatives within the pyrazolo[1,5-a]-1,3,5-triazine series. Preliminary biological testing has shown that compound 2 strongly inhibits ADP-induced human platelet aggregation and shape change and possesses significant efficacies 30 min after injection in rat, highlighting a strong P2Y(1)-receptor antagonist activity in vitro combined with a prolonged duration of action in vivo.