89179-80-6

Basic information

• Product Name: 1H-Pyrazole-1-carboxamide,2,5-dihydro-3-methyl-5-oxo-(9CI)
• Synonyms: 1H-Pyrazole-1-carboxamide,2,5-dihydro-3-methyl-5-oxo-(9CI)
• CAS NO: 89179-80-6
• Molecular Formula: C₅H₇N₃O₂
• Molecular Weight: 141.12798
• Product Categories: AMIDE
• Mol File: 89179-80-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrazole-1-carboxamide,2,5-dihydro-3-methyl-5-oxo-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-1-carboxamide,2,5-dihydro-3-methyl-5-oxo-(9CI)(89179-80-6)
• EPA Substance Registry System: 1H-Pyrazole-1-carboxamide,2,5-dihydro-3-methyl-5-oxo-(9CI)(89179-80-6)

Safety Data

• Hazardous Substances Data: 89179-80-6(Hazardous Substances Data)

Usage

Purpose

Important chemotherapy drug for treating brain tumors like glioblastoma multiforme.

Mechanism of Action

Alkylating agent that disrupts the growth and spread of cancer cells by attaching an alkyl group to DNA, causing DNA damage and leading to cancer cell death.

Clinical Trials

Has shown promising results in clinical trials.

Regulatory Approval

Approved for use by regulatory agencies in many countries.

Side Effects

Can cause nausea, vomiting, and hair loss.

Upstream product

• 141-97-9 ethyl acetoacetate 
• 4426-72-6 hydrazine carboxamide 

Downstream Products

• 108-26-9 3-methyl-2-pyrazoline-5-one 

Relevant articles and documents

Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate

A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH 3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.