103405-98-7

Basic information

• Product Name: 2-CHLORO-N-{[(3,4-DIMETHYLPHENYL)AMINO]CARBONYL}ACETAMIDE
• Synonyms: 2-chloro-N-[(3,4-dimethylphenyl)carbamoyl]acetamide
• CAS NO: 103405-98-7
• Molecular Formula: C₁₁H₁₃ClN₂O₂
• Molecular Weight: 240.69
• Mol File: 103405-98-7.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.274g/cm³
• Refractive Index: 1.584
• CAS DataBase Reference: 2-CHLORO-N-{[(3,4-DIMETHYLPHENYL)AMINO]CARBONYL}ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-{[(3,4-DIMETHYLPHENYL)AMINO]CARBONYL}ACETAMIDE(103405-98-7)
• EPA Substance Registry System: 2-CHLORO-N-{[(3,4-DIMETHYLPHENYL)AMINO]CARBONYL}ACETAMIDE(103405-98-7)

Safety Data

• Hazardous Substances Data: 103405-98-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13ClN2O2/c1-7-3-4-9(5-8(7)2)13-11(16)14-10(15)6-12/h3-5H,6H2,1-2H3,(H2,13,14,15,16)

Upstream product

• 4461-30-7 2-chloroacetylisocyanate 
• 95-64-7 4-amino-o-xylene 

Downstream Products

• 38523-90-9 N-(3,4-dimethyl-phenylcarbamoyl)-2-morpholin-4-yl-acetamide 

Relevant articles and documents

Quinoxaline-based inhibitors of Ebola and Marburg VP40 egress

We prepared a series of quinoxalin-2-mercapto-acetyl-urea analogs and evaluated them for their ability to inhibit viral egress in our Marburg and Ebola VP40 VLP budding assays in HEK293T cells. We also evaluated selected compounds in our bimolecular complementation assay (BiMC) to detect and visualize a Marburg mVP40–Nedd4 interaction in live mammalian cells. Antiviral activity was assessed for selected compounds using a live recombinant vesicular stomatitis virus (VSV) (M40 virus) that expresses the EBOV VP40 PPxY L-domain. Finally selected compounds were evaluated in several ADME assays to have an early assessment of their drug properties. Our compounds had low nM potency in these assays (e.g., compounds 21, 24, 26, 39), and had good human liver microsome stability, as well as little or no inhibition of P450 3A4.

Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site

A number of N-phenyl-N′-(2-chloroethyl)ureas (CEUs) have been shown to be potent antimitotics through their covalent binding to the colchicine-binding site on intracellular β-tubulin. The present communication aimed to evaluate the role of the electrophilic 2-chloroethyl amino moiety of CEU on cell growth inhibition and the specificity of the drugs as irreversible antagonists of the colchicine-binding site. To that end, several N-phenyl-N′-(2-ethyl)urea (EU), N-phenyl-N′-(2-chloroethyl)urea (CEU), N-aryl amino-2-oxazoline (OXA), and N-phenyl-N′-(2-chloroacetyl)urea (CAU) derivatives were prepared and tested for their antiproliferative activity, their effect on the cell cycle, and their irreversible binding to β-tubulin. EU derivatives were devoid of antiproliferative activity. CEUs (2h-2i, 2k, 2l, OXA 3e, 3h, 3i, 3k, 3l, tBCEU, and ICEU), OXA (3h, 3i, 3k, 3l, tBOXA, and IOXA), and CAU (4a-4m, tBCAU, and ICAU) had GI50 between 1.7 and 10 μM on three tumor cell lines. Cytotoxic CEU and OXA arrested the cell cycle in G2/M phase, while the corresponding CAU were not phase specific. Finally, Western blot analysis clearly showed that only CEUs 2h, 2k, 2l, tBCEU, ICEU and OXA 3h, 3i, 3k, 3l, tBOXA,and IOXA were able to bind irreversibly to the colchicine-binding site. Our results suggest that increasing the potency of the electrophilic moiety of the aromatic ureas enhances their antiproliferative activity but decreases significantly their capacity to covalently bind to the colchicine-binding site.