13908-40-2

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea is utilized as an intermediate in the production of various pharmaceuticals. Its unique chemical structure allows for the creation of a wide range of medicinal compounds, contributing to the development of new treatments and therapies.
Used in Agrochemical Production:
In the agrochemical industry, 1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea serves as a crucial intermediate for the synthesis of different agrochemicals. These products are essential for enhancing crop protection and improving agricultural yields.
Used as a Reagent in Organic Synthesis:
1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea also finds application as a reagent in organic synthesis, where it aids in the formation of complex organic molecules. Its versatility in chemical reactions makes it a valuable tool for researchers and chemists working on the development of new organic compounds.
Used as a Pesticide:
1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea is employed as a pesticide, helping to protect crops from pests and diseases. Its effectiveness in controlling various pests makes it a valuable asset in the agricultural sector.
Safety Precautions:
It is essential to handle 1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea with care and follow proper safety protocols, as it can be harmful if ingested, inhaled, or comes into contact with skin and eyes. Appropriate protective measures should be taken to minimize the risk of exposure and ensure the safety of those working with 1-(2-chloroethyl)-3-(2,6-dimethylphenyl)urea.

Upstream product

• 1943-83-5 2-chloroethyl isothiocyanate 
• 87-62-7 2,6-dimethylaniline 

Downstream Products

• 31235-50-4 (4,5-dihydro-oxazol-2-yl)-(2,6-dimethyl-phenyl)-amine 
• 91180-66-4 1-(2,6-dimethyl-phenyl)-imidazolidin-2-one 
• 13909-20-1 C₁₁H₁₄ClN₃O₂ 

Relevant academic research and scientific papers

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.

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.

New substituted 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidin-4-yl derivatives with α2-adrenoceptor antagonist activity

The emergence of a novel theory concerning the role of noradrenaline in the progression and the treatment of neurodegenerative diseases such as Parkinson's and Alzheimer's diseases has provided a new impetus toward the discovery of novel compounds acting at α2-adrenoceptors. A series of substituted 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidin-4-yl derivatives bearing an amide, urea, or imidazolidinone moiety was studied. Some members of this series of compounds proved to be potent α2-adrenoceptor antagonists with good selectivity versus α1-adrenergic and D2-dopamine receptors. Particular emphasis is given to compound 33g which displays potent α2-adrenoceptor binding affinity in vitro and central effects in vivo following oral administration.

Synthesis and cytotoxic activity of new alkyl[3-(2-chloroethyl)ureido]benzene derivatives

Several alkyl[3-(2-chloroethyl)ureido] (CEU) benzene derivatives were prepared as potential anticancer agents. These new compounds were readily prepared in good yields by addition of anilines to 2-chloroethylisocyanate. Their cytotoxic activity was evaluated on human breast cancer (MDA-MB-231), human colon adenocarcinoma (LoVo) and mouse lymphocytic leukemia (P388D1) tumor cell lines. Several new CEUs were significantly more cytotoxic than the nitrogen mustard chlorambucil. The biological activity of these aromatic urea derivatives seems to be related to the nature and position of the alkyl substituents on the aromatic ring. Substitution by branched alkyl groups on position 4 of the aromatic ring led to cytotoxic molecules which are up to 5 times more potent than the standard chlorambucil.