364334-94-1

Basic information

• Product Name: 4-(2,4-DIMETHYL-1,3-THIAZOL-5-YL)PYRIMIDIN-2-AMINE
• Synonyms: 4-(2,4-DIMETHYL-1,3-THIAZOL-5-YL)PYRIMIDIN-2-AMINE;4-(diMethyl-1,3-thiazol-5-yl)pyriMidin-2-aMine;4-(2,4-Dimethylthiazol-5-yl)pyrimidin-2-amine
• CAS NO: 364334-94-1
• Molecular Formula: C₉H₁₀N₄S
• Molecular Weight: 206.2675
• Mol File: 364334-94-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(2,4-DIMETHYL-1,3-THIAZOL-5-YL)PYRIMIDIN-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,4-DIMETHYL-1,3-THIAZOL-5-YL)PYRIMIDIN-2-AMINE(364334-94-1)
• EPA Substance Registry System: 4-(2,4-DIMETHYL-1,3-THIAZOL-5-YL)PYRIMIDIN-2-AMINE(364334-94-1)

Safety Data

• Hazardous Substances Data: 364334-94-1(Hazardous Substances Data)

Usage

General Description

The chemical 4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-amine, also known as thiamethoxam, is a neonicotinoid insecticide used in agricultural and horticultural to control a wide range of pests, including aphids, whiteflies, and leafhoppers. It acts as an agonist of the nicotinic acetylcholine receptors, disrupting the insect's nervous system and ultimately leading to paralysis and death. Thiamethoxam is highly effective against target pests and has low toxicity to mammals, making it widely used in crop protection. However, concerns have been raised about its potential impact on non-target insects, including bees, and its persistence in the environment. Therefore, its use is regulated in many countries to minimize its impact on non-target organisms.

Upstream product

• 124-46-9 guanidine hydrogen carbonate 
• 38205-60-6 5-acetyl-2,4-dimethylthiazole 
• 113-00-8 guanidine nitrate 

Relevant articles and documents

2-Anilino-4-(thiazol-5-yl)pyrimidine CDK Inhibitors: Synthesis, SAR Analysis, X-ray Crystallography, and Biological Activity

Following the identification through virtual screening of 4-(2,4-dimethyl-thiazol-5-yl)pyrimidin-2-ylamines as moderately potent inhibitors of cyclin-dependent kinase-2 (CDK2), a CDK inhibitor analogue program was initiated. The first aims were to optimize potency and to evaluate the cellular mode of action of lead candidate molecules. Here the synthetic chemistry, the structure-guided design approach, and the structure-activity relationships (SARs) that led to the discovery of 2-anilino-4-(thiazol-5-yl)pyrimidine ATP-antagonistic CDK2 inhibitors, many with very low nM Kis against CDK2, are reported. Furthermore, X-ray crystal structures of four representative analogues from our chemical series in complex with CDK2 are presented, and these structures are used to rationalize the observed biochemical SARs. Finally results are reported that show, using the most potent CDK2 inhibitor compound from the current series, that the observed antiproliferative and proapoptotic effects are consistent with cellular CDK2 and CDK9 inhibition.