150885-24-8

Basic information

• Product Name: ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrrole-2-carboxylate
• Synonyms: ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrrole-2-carboxylate
• CAS NO: 150885-24-8
• Molecular Weight: 566.654
• Mol File: 150885-24-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrrole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrrole-2-carboxylate(150885-24-8)
• EPA Substance Registry System: ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrrole-2-carboxylate(150885-24-8)

Safety Data

• Hazardous Substances Data: 150885-24-8(Hazardous Substances Data)

Upstream product

• 50619-36-8 2,3,5-tri-Obenzyl-α,β-D-ribofuranosylchloride 
• 7126-44-5 3-Cyan-2-pyrrolcarbonsaeure-ethylester 

Downstream Products

• 150885-45-3 4-Amino-1-((2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-bromo-1,6-dihydro-pyrrolo[2,3-d]pyridazin-7-one 
• 150999-80-7 4-Amino-1-((2R,3R,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-chloro-1,6-dihydro-pyrrolo[2,3-d]pyridazin-7-one 
• 150885-25-9 4-amino-1-β-D-ribofuranosylpyrrole<2,3-d>pyridazin-7(6H)-one 
• 150885-28-2 4-amino-1-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrrole<2,3-d>pyridazin-7(6H)-one 

Relevant articles and documents

Synthesis, Antiproliferative, and Antiviral Activity of 4-Amino-1-(β-D-ribofuranosyl)pyrrolopyridazin-7(6H)-one and Related Derivatives

The synthesis of 4-amino-1-β-D-ribofuranosylpyrrolopyridazin-7(6H)-one (3) from the reaction of ethyl 3-cyano-1-β-D-ribofuranosylpyrrole-2-carboxylate (10) and hydrazine is described.The 5:6 pyrrolopyridazin-7(6H)-one structure of 3 was established via a three-step conversion of 3 into 1-β-D-ribofuranosylpyrrolopyridazin-4,7(5H,6H)-dione (14). 4-amino-3-chloro-1-β-D-ribofuranosylpyrrolopyridazin-7(6H)-one (16) and 4-amino-3-bromo-1-β-D-ribofuranosylpyrrolopyridazin-7(6H)-one (18) were prepared via N-chlorosuccinimide or N-bromosuccinimide treatment of 4-amino-1-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)pyrrolopyridazin-7(6H)-one (7) followed by a removal of the benzyl groups with boron trichloride.Direct treatment of 3 with N-iodosuccinimide furnished 4-amino-3-iodo-1-β-D-ribofuranosylpyrrolopyridazin-7(6H)-one (19).The antiproliferative activity of the compounds was determined in L1210, H.Ep. 2 and several additional human tumor cell lines.In L1210 cells, the 3-halosubstituted compounds 16, 18, and 19 exhibited significant cytotoxicity (IC50 = 0.2, 0.1, 0.08 μM, respectively), in contrast to the 3-unsubstituted compound 3, which had only slight activity.The greater antiproliferative activity of 18 and 19 in contrast to 3 was confirmed in H.Ep. 2 cells and KB cells.The antiviral evaluation of these compounds revealed that compounds 16, 18, and 19 were active against human cytomegalovirus in both plaque- and yield-reduction assays.However, this activity was only partially separated from cytotoxicity in human cell lines.