3910-51-8

Basic information

• Product Name: 2-CHLORO-N-(2,4,6-TRIMETHYL-PHENYL)-ACETAMIDE
• Synonyms: AKOS BBS-00004044;AKOS BOR-BB-011;2-CHLORO-N-(2,4,6-TRIMETHYL-PHENYL)-ACETAMIDE;2-chloro-N-(2,4,6-trimethylphenyl)ethanamide
• CAS NO: 3910-51-8
• Molecular Formula: C₁₁H₁₄ClNO
• Molecular Weight: 211.69
• Mol File: 3910-51-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 324.1°C at 760 mmHg
• Flash Point: 149.8°C
• Appearance: /
• Density: 1.158g/cm³
• Vapor Pressure: 0.000252mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: 2-CHLORO-N-(2,4,6-TRIMETHYL-PHENYL)-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-(2,4,6-TRIMETHYL-PHENYL)-ACETAMIDE(3910-51-8)
• EPA Substance Registry System: 2-CHLORO-N-(2,4,6-TRIMETHYL-PHENYL)-ACETAMIDE(3910-51-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 3910-51-8(Hazardous Substances Data)

Usage

Uses

Chloracetmesidide is an intermediate in the synthesis of Trimecaine Hydrochloride (T765620), a local anesthetic and cardial antiarrhythmic. Trimecaine Hydrochloride is used in epidural postoperative analgesia after major urological procedures in combination with morphine.

InChI:InChI=1/C11H14ClNO/c1-7-4-8(2)11(9(3)5-7)13-10(14)6-12/h4-5H,6H2,1-3H3,(H,13,14)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 88-05-1 2,4,6-trimethylaniline 
• 603-71-4 nitromesitylene 

Downstream Products

• 101353-87-1 pyrrolidino-acetic acid-(2,4,6-trimethyl-anilide) 
• 101354-20-5 2-morpholin-4-yl-N-(2,4,6-trimethyl-phenyl)-acetamide 
• 101353-93-9 2-thiomorpholin-4-yl-N-(2,4,6-trimethyl-phenyl)-acetamide 
• 109156-59-4 (4-methyl-piperidino)-acetic acid-(2,4,6-trimethyl-anilide) 
• 123202-86-8 2-(4-Hydroxy-piperidin-1-yl)-N-(2,4,6-trimethyl-phenyl)-acetamide 
• 93990-42-2 nortropanomesidide 
• 108086-46-0 2-(4-Oxo-4H-quinazolin-3-yl)-N-(2,4,6-trimethyl-phenyl)-acetamide 
• 121513-22-2 2-(4-Phenyl-piperazin-1-yl)-N-(2,4,6-trimethyl-phenyl)-acetamide 
• 118564-50-4 2-Azepan-1-yl-N-(2,4,6-trimethyl-phenyl)-acetamide 
• 123202-83-5 2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-N-(2,4,6-trimethyl-phenyl)-acetamide 
• 103395-51-3 (3-methyl-piperidino)-acetic acid-(2,4,6-trimethyl-anilide) 
• 109157-85-9 (2-methyl-piperidino)-acetic acid-(2,4,6-trimethyl-anilide) 
• 616-68-2 trimecaine 
• 91904-31-3 N,N-dimethyl-glycine-(2,4,6-trimethyl-anilide) 

Relevant articles and documents

Synthesis, biological evaluation, and structure-activity relationships of new tubulin polymerization inhibitors based on 5-amino-1,2,4-triazole scaffold

Based on our previous research, thirty new 5-amino-1H-1,2,4-triazoles possessing 3,4,5-trimethoxyphenyl moiety were synthesized, and evaluated for antiproliferative activities. Among them, compounds IIa, IIIh, and IIIm demonstrated significant antiproliferative activities against a panel of tumor cell lines, and the promising compound IIIm dose-dependently caused G2/M phase arrest in HeLa cells. Furthermore, analogue IIa exhibited the most potent tubulin polymerization inhibitory activity with an IC50 value of 9.4 μM, and molecular modeling studies revealed that IIa formed stable interactions in the colchicine-binding site of tubulin, suggesting that 5-amino-1H-1,2,4-triazole scaffold has potential for further investigation to develop novel tubulin polymerization inhibitors with anticancer activity.

Discovery and optimization of 3,4,5-trimethoxyphenyl substituted triazolylthioacetamides as potent tubulin polymerization inhibitors

Based on our previous research, three series of new triazolylthioacetamides possessing 3,4,5-trimethoxyphenyl moiety were synthesized, and evaluated for antiproliferative activities and inhibition of tubulin polymerization. The most promising compounds 8b and 8j demonstrated more significant antiproliferative activities against MCF-7, HeLa, and HT-29 cell lines than our lead compound 6. Moreover, analogues 8f, 8j, and 8o manifested more potent antiproliferative activities against HeLa cell line with IC50 values of 0.04, 0.05 and 0.16 μM, respectively, representing 100-, 82-, and 25-fold improvements of the activity compared to compound 6. Furthermore, the representative compound, 8j, was found to induce significant cell cycle arrest at the G2/M phase in HeLa cell lines via a concentration-dependent manner. Meanwhile, compound 8b exhibited the most potent tubulin polymerization inhibitory activity with an IC50 value of 5.9 μM, which was almost as active as that of CA-4 (IC50 = 4.2 μM). Additionally, molecular docking analysis suggested that 8b formed stable interactions in the colchicine-binding site of tubulin.

THIAZOLOPYRIMIDINONE COMPOUNDS AND PREPARATION METHODS AND USE THEREOF

The present invention provides structural details of a thiazolopyrimidinone compound, a preparation method thereof, and use thereof in the manufacture of a medicament for the treatment of central nervous system diseases.