16867-45-1

Basic information

• Product Name: N-(4-methylpyridin-2-yl)-3-oxobutanamide
• Synonyms: N-(4-methylpyridin-2-yl)-3-oxobutanamide;N-(4-Methyl-2-pyridinyl)-3-oxobutanamide;N-(4-Methyl-2-pyridyl)acetoacetamide
• CAS NO: 16867-45-1
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192
• Mol File: 16867-45-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 122-123℃
• Boiling Point: 407.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.185
• PKA: 10.71±0.46(Predicted)
• CAS DataBase Reference: N-(4-methylpyridin-2-yl)-3-oxobutanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-methylpyridin-2-yl)-3-oxobutanamide(16867-45-1)
• EPA Substance Registry System: N-(4-methylpyridin-2-yl)-3-oxobutanamide(16867-45-1)

Safety Data

• Hazardous Substances Data: 16867-45-1(Hazardous Substances Data)

Usage

Description

N-(4-methylpyridin-2-yl)-3-oxobutanamide, also known as MK-1775, is a chemical compound with the molecular formula C10H12N2O2. It is a potent inhibitor of the enzyme Wee1 kinase, which is involved in the cell cycle checkpoint and DNA damage response. By inhibiting Wee1 kinase, N-(4-methylpyridin-2-yl)-3-oxobutanamide can lead to the accumulation of DNA damage and cell death, making it a promising candidate for anticancer applications.

Uses

Used in Oncology:
N-(4-methylpyridin-2-yl)-3-oxobutanamide is used as an anticancer agent for its ability to inhibit the Wee1 kinase enzyme, which plays a crucial role in the cell cycle checkpoint and DNA damage response. This inhibition can lead to the accumulation of DNA damage and cell death, making it a potential treatment for various types of cancers.
Used in Combination Therapy:
N-(4-methylpyridin-2-yl)-3-oxobutanamide is used in combination with other chemotherapeutic drugs to enhance their efficacy in killing cancer cells. By inhibiting the Wee1 kinase enzyme, it can increase the susceptibility of cancer cells to the effects of other treatments, leading to improved outcomes for patients.
Clinical Trials:
N-(4-methylpyridin-2-yl)-3-oxobutanamide is currently being studied in clinical trials to evaluate its potential as a treatment for various types of cancers. These trials aim to determine the safety, efficacy, and optimal dosing regimens for this compound in cancer therapy.

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 695-34-1 2-Amino-4-methylpyridine 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 1092459-64-7 (Z)-2-anilino-2-(oxido(phenyl)imino)-N-(4-methylpyridin-2-yl)acetamide 
• 1092459-67-0 (Z)-2-(4-methylphenyl)-2-[oxido(4-methylphenyl)imino]-N-(4-methylpyridin-2-yl)acetamide 
• 22365-23-7 4,8-dimethyl-2-oxo-(2H)-pyrido[1,2-a]pyrimidine 

Relevant articles and documents

Antiproliferative effect, alteration of cancer cell cycle progression and potential MET kinase inhibition induced by 3,4-dihydropyrimidin-2(1H)-one C5 amide derivatives

Cancer continues to be the second leading cause of death worldwide. Discovery of novel therapeutic agents has crucial importance for improvement of our medical management capabilities. Dysregulation of the MET receptor tyrosine kinase pathway plays an important role in cancer progression, making this receptor an attractive molecular target for anticancer drug discovery. In this study, twenty-seven 3,4-dihydropyrimidin-2(1H)-one C5 amide derivatives were synthesized and their cancer cell growth inhibitory activity was examined against MCF-7, HT-29 and MOLT-4 cells and also NIH/3T3 non-cancer cells by MTT assay. The antiproliferative effect of the most potent derivatives were tested against MET-dependent EBC-1 and MKN-45, lung and gastric cancer cell lines, respectively. MET kinase inhibition was measured by a Homogenous Time Resolved Fluorescence (HTRF) Assay. The influence of the test compounds on cell cycle was examined by RNase/PI flow cytometric assay. A number of compounds exhibited considerable antiproliferative effects against breast and colon cancer and leukemia cell lines, relatively sparing non-cancer cells. Some derivatives bearing benzothiazolyl carboxamide moiety at C5 position (15, 21, 23, 31, and 37) showed the highest activities with IC50 values as low as 10.9 μM. These compounds showed antiproliferative effects also against MET-amplified cells and dose-dependently inhibited MET kinase activity. They also induced G0/G1 cell cycle arrest at lower doses and apoptosis at higher doses. Molecular docking and dynamics simulation studies confirmed the interaction of compound 23 with the active site of the MET receptor. These findings demonstrate that 3,4-dihydropyrimidin-2(1H)-one analogues may represent promising targeted anticancer agents.

Substrate- and base-dependent reactivities of acylketene toward aryl aldimines derived from 2-amino-4-methylpyridine

Acylketene, generated from 2,2,6-trimethyl-4H-1,3-dioxin-4-one reacts with aryl aldimines derived from 4-methyl-2-aminopyridine to give a variety of products, depending on the substituent on the C-aryl group, base used, and hydrolytic stability of the starting aldimine. Also the presence of the N-(2-pyridyl) group plays an important role in the fate of the reaction course, frequently participating in intramolecular conjugate additions, giving rise to interesting heterocycles.

CERTAIN COMPOUNDS, COMPOSITIONS, AND METHODS

Compounds useful for treating cellular proliferative diseases are disclosed.