136944-79-1

Basic information

• Product Name: 1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester
• Synonyms: 1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester;4-Iodo-1H-pyrazole-3-carboxylic acid methyl ester;methyl 4-iodo-1H-pyrazole-5-carboxylate;MFCD09473436
• CAS NO: 136944-79-1
• Molecular Formula: C₅H₅IN₂O₂
• Molecular Weight: 252.01
• Mol File: 136944-79-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester(136944-79-1)
• EPA Substance Registry System: 1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester(136944-79-1)

Safety Data

• Hazardous Substances Data: 136944-79-1(Hazardous Substances Data)

Usage

General Description

1H-Pyrazole-3-carboxylic acid, 4-iodo-, methyl ester is a chemical compound represented by the molecular formula C6H5IN2O2. It belongs to the group of Pyrazoles which are aromatic organic compounds characterized by a 5-membered ring with two nitrogen atoms. The compound is characterized by the presence of a pyrazole ring, a carboxylic acid group, a methyl ester group, and an iodine atom. While specific usage information may not be readily available given the somewhat specialized nature of this compound, it could potentially be used in scientific research or as an intermediate in the synthesis of more complex chemical substances.

Upstream product

• 15366-34-4 methyl 1H-pyrazole 3-carboxylate 

Downstream Products

• 273410-26-7 4-iodo-3-methoxycarbonyl-1-{[1,3-bis(benzyloxy)-2-propoxy]methyl}-pyrazole 
• 138786-93-3 methyl 1-(β-D-2',3',5'-tri-O-benzoylribofuranosyl)-4-iodo-pyrazole-3-carboxylate 

Relevant articles and documents

Electrosynthesis of 4-iodopyrazole and its derivatives

Electrosynthesis of 4-iodo-substituted pyrazoles has been accomplished by iodination of the corresponding precursors on a Pt-anode in aqueous solutions of KI under conditions of the diaphragm galvanostatic electrolysis. Efficiency of the process depends on the donor-acceptor properties of substituents and their positions in the pyrazole ring. Thus, iodination of pyrazole, 3,5-dimethylpyrazole, 3-nitropyrazole, 1-methylpyrazole, 1,3-dimethylpyrazole, pyrazole-3(5)-carboxylic acid or methyl esters furnished 4-iodo derivatives in 57, 86, 2, 5, 35, 30, and 40% yields, respectively.

PYRAZOLE DERIVATIVES AS MODULATORS OF THE WNT/B-CATENIN SIGNALING PATHWAY

Pyrazole compounds (I) for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of a pyrazole compounds, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis Alzheimer's disease, lung disease, inflammation, auto-immune diseases and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as neurological conditions/disorders/diseases linked to overexpression of DYRK1A.

Effects of introduction of hydrophobic group on ribavirin base on mutation induction and anti-RNA viral activity

One of the possible mechanisms of antiviral action of ribavirin (1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide, 1) is the accumulation of mutations in viral genomic RNA. The ambiguous incorporation of 5′-triphosphate of ribavirin (RTP, 8) by a viral RNA-dependent RNA polymerase (RdRp) is a key step of the mutation induction. We synthesized three ribavirin analogues that possess hydrophobic groups, 4-iodo-1-β-D- ribofuranosylpyrazole-3-carboxamide (7a), 4-propynyl-1-β-D- ribofuranosylpyrazole-3-carboxamide (7b), and 4-phenylethynyl-1-β-D- ribofuranosylpyrazole-3-carboxamide (7c), and the corresponding triphosphates (9a, 9b, and 9c, respectively). Steady-state kinetics analysis of the incorporation of these triphosphate analogues by a poliovirus RdRp, 3D pol, revealed that while the incorporation efficiency of 9a was comparable to RTP, 9b and 9c showed lower efficiency than RTP. Antipolioviral activity of 7a and 7b was much more moderate than ribavirin, and 7c showed no antipolioviral activity. Effects of substituting groups on the incorporation efficiency by 3Dpol and a strategy for a rational design of more active ribavirin analogues are discussed.