138787-01-6

Basic information

• Product Name: 4-iodo-1-(beta-D-ribofuranosyl)-1H-pyrazole-3-carboxamide
• Synonyms: 1-.beta.-D-Ribofuranosyl-4-iodopyrazole-3-carboxamide; 1-beta-D-Ribofuranosyl-4-iodopyrazole-3-carboxamide; 1H-pyrazole-3-carboxamide, 4-iodo-1-beta-D-ribofuranosyl-
• CAS NO: 138787-01-6
• Molecular Formula: C₉H₁₂IN₃O₅
• Molecular Weight: 369.1132
• Mol File: 138787-01-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 651.2°C at 760 mmHg
• Flash Point: 347.6°C
• Density: 2.52g/cm³
• Vapor Pressure: 7.58E-18mmHg at 25°C
• Refractive Index: 1.85
• CAS DataBase Reference: 4-iodo-1-(beta-D-ribofuranosyl)-1H-pyrazole-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-iodo-1-(beta-D-ribofuranosyl)-1H-pyrazole-3-carboxamide(138787-01-6)
• EPA Substance Registry System: 4-iodo-1-(beta-D-ribofuranosyl)-1H-pyrazole-3-carboxamide(138787-01-6)

Safety Data

• Hazardous Substances Data: 138787-01-6(Hazardous Substances Data)

Upstream product

• 138786-93-3 methyl 1-(β-D-2',3',5'-tri-O-benzoylribofuranosyl)-4-iodo-pyrazole-3-carboxylate 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 

Downstream Products

• 1002761-65-0 4-iodo-1-β-D-ribofuranosylpyrazole-3-carboxamide 5'-triphosphate 

Relevant articles and documents

Design, synthesis and antiproliferative activity of methyl 4-iodo-1-β-D- ribofuranosyl-pyrazole-3-carboxylate and related compounds

In a SAR study on azole-related nucleosides we have designed some pyrazole-nucleoside analogs characterised, for the first time, by a carboxylic ester moiety. 4-Iodo-1-β-D-ribofuranosyl-pyrazole-3-carboxylate showed a wide spectrum of antiproliferative activity and a particularly low cytotoxicity against resting PBL, being, unlike the other azole nucleosides, more active than the corresponding primary amide.

Pyrazole-related nucleosides.1 Design, synthesis and antiproliferative activity of methyl 4-iodo-1-β-D-ribofuranosylpyrazole-3-carboxylate (IPCAR), and derivatives, against human leukemias, lymphomas and solid tumors cell lines in vitro

A structure-activity relationship (SAR) study on some new 1-β-D-ribofuranosyl-3,4-substituted pyrazole derivatives led us to obtain 4-iodo-1-β-D-ribofuranosyl-pyrazole-3-carboxylate (3, IPCAR) and its 3-methyl-1,2,4-oxadiazole analog (11) at position C3. These compounds showed good potency, wide spectrum of antiproliferative activity and low cytotoxicity against resting peripheral blood lymphocytes (PBL). Although none of the test compounds displayed antiviral activity, IPCAR was able to potentiate the anti-HIV-1 activity of dideoxyinosine (ddI), thus behaving like the known inosine monophosphate dehydrogenase (IMPDH) inhibitors ribavirin and tiazofurin. The corresponding methyl esters of the latter two drugs (15 and 16) were also prepared, but they proved inactive. Overall, these results suggest that the target of IPCAR may be an enzyme other than IMPDH involved in the purine de novo biosynthesis.