102433-52-3

Basic information

• Product Name: 1-(2-chloroethyl)-3-(2,3-dihydro-1H-inden-5-yl)urea
• Synonyms: urea, N-(2-chloroethyl)-N'-(2,3-dihydro-1H-inden-5-yl)-
• CAS NO: 102433-52-3
• Molecular Formula: C₁₂H₁₅ClN₂O
• Molecular Weight: 238.7133
• Mol File: 102433-52-3.mol

Chemical Properties

• Boiling Point: 354.3°C at 760 mmHg
• Flash Point: 168.1°C
• Density: 1.267g/cm³
• Vapor Pressure: 3.39E-05mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 1-(2-chloroethyl)-3-(2,3-dihydro-1H-inden-5-yl)urea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-chloroethyl)-3-(2,3-dihydro-1H-inden-5-yl)urea(102433-52-3)
• EPA Substance Registry System: 1-(2-chloroethyl)-3-(2,3-dihydro-1H-inden-5-yl)urea(102433-52-3)

Safety Data

• Hazardous Substances Data: 102433-52-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-chloroethyl)-3-(2,3-dihydro-1H-inden-5-yl)urea is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows for the creation of drugs with potential anti-cancer or anti-inflammatory properties, contributing to the development of novel therapeutic options.
Used in Agrochemical Industry:
In the agrochemical industry, 1-(2-chloroethyl)-3-(2,3-dihydro-1H-inden-5-yl)urea is used as a building block for the development of new agrochemicals. Its chemical properties make it suitable for the creation of compounds that can be applied in agriculture to enhance crop protection and yield.
Used in Materials Science:
1-(2-chloroethyl)-3-(2,3-dihydro-1H-inden-5-yl)urea is also utilized in the field of materials science. Its chemical structure can be manipulated to produce materials with specific properties, such as improved strength, durability, or chemical resistance, which can be applied in various industrial applications.
Used in Medicinal Chemistry Research:
As a valuable tool for researchers, 1-(2-chloroethyl)-3-(2,3-dihydro-1H-inden-5-yl)urea is used in medicinal chemistry research to explore its potential in the development of new drugs. Its unique structure and properties make it an interesting candidate for the creation of compounds with anti-cancer or anti-inflammatory effects, which could lead to breakthroughs in the treatment of various diseases.

Upstream product

• 1943-83-5 2-chloroethyl isothiocyanate 
• 24425-40-9 indan-5-amine 

Relevant articles and documents

Cycloalkyl-substituted aryl chloroethylureas inhibiting cell cycle progression in G0/G1 phase and thioredoxin-1 nuclear translocation

1-(2-Chloroethyl)-3-(4-cyclohexylphenyl)urea (cHCEU) has been shown to abrogate the presence of thioredoxin-1 into the nucleus through its selective covalent alkylation. In the present letter we have evaluated the structure-activity relationships of the s

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.

Aryl-chloro-ethyl ureas

Described herein are novel 1-aryl-3-(2-chloroalkanylureas derivatives. These derivatives are useful anticaner agents having excellent specifilty towards cell targets and potent antineoplastic activity without systemic toxicity derivatives mutagenicity. Mo

Antimitotic antitumor agents: Synthesis, structure-activity relationships, and biological characterization of N-aryl-N′-(2-chloroethyl)ureas as new selective alkylating agents

A series of N-aryl-N′-(2-chloroethyl)ureas (CEUs) and derivatives were synthesized and evaluated for antiproliferative activity against a wide panel of tumor cell lines. Systematic structure-activity relationship (SAR) studies indicated that: (i) a branched alkyl chain or a halogen at the 4-position of the phenyl ring or a fluorenyl/indanyl group, (ii) an exocyclic urea function, and (iii) a N′-2-chloroethyl moiety were required to ensure significant cytotoxicity. Biological experiments, such as immunofluorescence microscopy, confirmed that these promising compounds alter the cytoskeleton by inducing microtubule depolymerization via selective alkylation of β-tubulin. Subsequent evaluations demonstrated that potent CEUs were weak alkylators, were non-DNA-damaging agents, and did not interact with the thiol function of either glutathione or glutathione reductase. Therefore, CEUs are part of a new class of antimitotic agents. Finally, among the series of CEUs evaluated, compounds 12, 15, 16, and 27 were selected for further in vivo trials.

Certain aryl-ureido anti-cancer agents

The present invention is concerned with novel anticancer agents having potent antineoplastic activity without systemic toxicity and mutagenicity. The novel anticancer agents of the present invention are derivatives of formula I: STR1 wherein: A is O or NH