100517-70-2

Basic information

• Product Name: 4-METHYL-2-PHENYL-5-PYRIMIDINECARBOHYDRAZIDE
• Synonyms: BUTTPARK 98\18-64;4-METHYL-2-PHENYL-5-PYRIMIDINECARBOHYDRAZIDE
• CAS NO: 100517-70-2
• Molecular Formula: C₁₂H₁₂N₄O
• Molecular Weight: 228.25
• Mol File: 100517-70-2.mol

Chemical Properties

• Melting Point: 185 °C
• Appearance: /
• Density: 1.234g/cm³
• Refractive Index: 1.612
• CAS DataBase Reference: 4-METHYL-2-PHENYL-5-PYRIMIDINECARBOHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-2-PHENYL-5-PYRIMIDINECARBOHYDRAZIDE(100517-70-2)
• EPA Substance Registry System: 4-METHYL-2-PHENYL-5-PYRIMIDINECARBOHYDRAZIDE(100517-70-2)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 100517-70-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-METHYL-2-PHENYL-5-PYRIMIDINECARBOHYDRAZIDE is used as a potential therapeutic agent for cancer treatment due to its ability to inhibit the growth of cancer cells. It targets DNA damage repair enzymes, which can make cancer cells more susceptible to the effects of radiation therapy and certain chemotherapeutic agents.
In Cancer Research:
4-METHYL-2-PHENYL-5-PYRIMIDINECARBOHYDRAZIDE is utilized in laboratory studies to explore its efficacy in inhibiting the growth of various types of cancer cells. 4-METHYL-2-PHENYL-5-PYRIMIDINECARBOHYDRAZIDE has shown promising results, and ongoing research is aimed at understanding its full potential and optimizing its use as a cancer treatment.
In Drug Development:
As a compound with demonstrated potential in cancer cell inhibition, 4-METHYL-2-PHENYL-5-PYRIMIDINECARBOHYDRAZIDE is used in the development of new drugs that could offer novel treatment options for cancer patients. Its role in DNA repair inhibition suggests it may be particularly useful in combination therapies that enhance the effectiveness of existing cancer treatments.

InChI:InChI=1/C12H12N4O/c1-8-10(12(17)16-13)7-14-11(15-8)9-5-3-2-4-6-9/h2-7H,13H2,1H3,(H,16,17)

Upstream product

• 70733-12-9 ethyl 4-methyl-2-phenyl-5-pyrimidinecarboxylate 
• 134653-70-6 ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate 

Downstream Products

• 1604047-99-5 (E)-N′-(4-(dimethylamino)Benzylidene)-N,4-dimethyl-2-phenylpyrimidine-5-carbohydrazide 
• 1604047-94-0 N′-(4-(dimethylamino)benzylidene)-4-methyl-2-phenylpyrimidine-5-carbohydrazide 
• 1604048-02-3 N′-(4-(dimethylamino)benzylidene)-4-methyl-2-phenylpyrimidine-5-carbohydrazide 

Relevant articles and documents

Characterization of amide bond conformers for a novel heterocyclic template of N-acylhydrazone derivatives

Herein we describe NMR experiments and structural modifications of 4-methyl-2-phenylpyrimidine-N-acylhydrazone compounds (aryl-NAH) in order to discover if duplication of some signals in their 1H- and 13C-NMR spectra was related to a mixture of imine double bond stereoisomers (E/Z) or CO-NH bond conformers (syn and anti-periplanar). NMR data from NOEdiff, 2D-NOESY and 1H-NMR spectra at different temperatures, and also the synthesis of isopropylidene hydrazone revealed the nature of duplicated signals of a 4-methyl-2-phenylpyrimidine-N-acylhydrazone derivative as a mixture of two conformers in solution. Further we investigated the stereoelectronic influence of substituents at the ortho position on the pyrimidine ring with respect to the carbonyl group, as well as the electronic effects of pyrimidine by changing it to phenyl. The conformer equilibrium was attributed to the decoplanarization of the aromatic ring and carbonyl group (generated by an ortho-alkyl group) and/or the electron withdrawing character of the pyrimidine ring. Both effects increased the rotational barrier of the C-N amide bond, as verified by the ΔG≠ values calculated from dynamic NMR. As far as we know, it is the first description of aryl-NAH compounds presenting two CO-NH bond-related conformations.