7144-13-0

Usage

Uses

Used in Agricultural Industry:
1-(2-chloroethyl)-3-phenylurea is used as a herbicidal agent for controlling grasses and broad-leaved weeds in agricultural settings. It is particularly effective when applied to crops such as cereals, potatoes, and sugar beets, where weed control is essential for optimal crop yield and quality. Additionally, it is utilized on non-crop land to prevent weed growth that could compete with desired vegetation or be a nuisance.

Upstream product

• 20729-41-3 acetaldehyde imine 
• 103-71-9 phenyl isocyanate 
• 13279-22-6 1-(phenylaminocarbonyl)aziridine 
• 1943-83-5 2-chloroethyl isothiocyanate 
• 62-53-3 aniline 

Downstream Products

• 27151-01-5 4,5-dihydro-N-phenyl-2-oxazolamine 
• 1848-69-7 1-phenylimidazolidin-2-one 
• 5488-50-6 N-(2-iodo-ethyl)-N'-phenyl-urea 
• 27151-01-5 2-(phenylimino)oxazolidine 
• 226724-37-4 1-hexyl-3-phenyl-imidazolidin-2-one 
• 201470-78-2 3-octyl-1-phenylimidazolidin-2-one 
• 173901-19-4 4-(3-hexyl-2-imidazolidinon-1-yl)benzenesulfonyl chloride 
• 201470-20-4 4-(3-octyl-2-imidazolidinon-1-yl)benzenesulfonyl chloride 
• 959780-53-1 N-4-[125I]iodophenyl-N'-2-chloroethylurea 
• 146257-20-7 4-iodo-[3-(2-chloroethyl)ureido]benzene 
• 1311945-59-1 2-methoxyphenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1311945-60-4 2-ethoxyphenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1311945-61-5 2-chlorophenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonate 
• 1311945-62-6 2-fluorophenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonate 

Relevant academic research and scientific papers

Hydroamination and Hydrophosphination of Isocyanates/Isothiocyanates under Catalyst-Free Conditions

Symmetrical and unsymmetrical N,N’-disubstituted as well as trisubstituted ureas/thioureas by the hydroamination of isocyanates/isothiocyanates, and various phosphathioureas by the hydrophosphination of isothiocyanates have been synthesized in good to excellent yields under catalyst-free and mild conditions. This protocol is also applicable for the efficient synthesis of chiral ureas and thioureas and common herbicides, such as fenuron and monuron.

The relationship between solvatochromic properties and in silico ADME parameters of new chloroethylnitrosourea derivatives with potential anticancer activity and their β-Cyclodextrin complexes

In view of the anticancer effect of nitrosoureas a set of four new N-(2-chloroethyl)-N-nitrosourea (CENU) derivatives was synthesized. An in silico absorption, distribution, metabolism, excretion and toxicity (ADME/Tox) prediction study revealed that the

4-(3-Alkyl-2-oxoimidazolidin-1-yl)-N-phenylbenzenesulfonamides as new antimitotic prodrugs activated by cytochrome P450 1A1 in breast cancer cells

The role and the importance of the sulfonate moiety in phenyl 4-(2-oxo-3-alkylimidazolidin-1-yl)benzenesulfonates (PAIB-SOs) were assessed using its bioisosteric sulfonamide equivalent leading to new cytochrome P450 1A1 (CYP1A1)-activated prodrugs designa

Activation of Phenyl 4-(2-Oxo-3-Alkylimidazolidin-1-yl)benzenesulfonates Prodrugs by CYP1A1 as New Antimitotics Targeting Breast Cancer Cells

Prodrug-mediated utilization of the cytochrome P450 (CYP) 1A1 to obtain the selective release of potent anticancer products within cancer tissues is a promising approach in chemotherapy. We herein report the rationale, preparation, biological evaluation, and mechanism of action of phenyl 4-(2-oxo-3-Alkylimidazolidin-1-yl)benzenesulfonates (PAIB-SOs) that are antimicrotubule prodrugs activated by CYP1A1. Although PAIB-SOs are inert in most cells tested, they are highly cytocidal toward several human breast cancer cells, including hormone-independent and chemoresistant types. PAIB-SOs are N-dealkylated into cytotoxic phenyl 4-(2-oxo-3-imidazolidin-1-yl)benzenesulfonates (PIB-SOs) in CYP1A1-positive cancer cells, both in vitro and in vivo. In conclusion, PAIB-SOs are novel chemotherapeutic prodrugs with no equivalent among current antineoplastics and whose selective action toward breast cancer is tailored to the characteristic pattern of CYP1A1 expression observed in a large percentage of human breast tumors.

SUBSTITUTED 2-IMIDAZOLIDONES AND ANALOGS

Compounds of formula (I): wherein R1, R2, R3, R4, R7, R6, R7, R8, R9, A, X and Y as defined herein are provided as useful for the treatment of cancer or for

Design, synthesis, biological evaluation, and Structure - Activity relationships of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates as new tubulin inhibitors mimicking combretastatin A-4

Sixty-one phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB-SOs) and 13 of their tetrahydro-2-oxopyrimidin-1(2H)-yl analogues (PPB-SOs) were prepared and biologically evaluated. The antiproliferative activities of PIB-SOs on 16 cancer cell lines are

Substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamides as antimitotics. Antiproliferative, antiangiogenic and antitumoral activity, and quantitative structure-activity relationships

The importance of the bridge linking the two phenyl moieties of substituted phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB-SOs) was assessed using a sulfonamide group, which is a bioisostere of sulfonate and ethenyl groups. Forty one phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamide (PIB-SA) derivatives were prepared and biologically evaluated. PIB-SAs exhibit antiproliferative activities at the nanomolar level against sixteen cancer cell lines, block the cell cycle progression in G2/M phase, leading to cytoskeleton disruption and anoikis. These results were subjected to CoMFA and CoMSIA analyses to establish quantitative structure-activity relationships. These results evidence that the sulfonate and sulfonamide moieties are reciprocal bioisosteres and that phenylimidazolidin-2-one could mimic the trimethoxyphenyl moiety found in the structure of numerous potent antimicrotubule agents. Finally, compounds 16 and 17 exhibited potent antitumor and antiangiogenic activities on HT-1080 fibrosarcoma cells grafted onto chick chorioallantoic membrane similar to CA-4 without significant toxicity for the chick embryos, making this class of compounds a promising class of anticancer agents.

Selective alkylation of βII-tubulin and thioredoxin-1 by structurally related subsets of aryl chloroethylureas leading to either anti-microtubules or redox modulating agents

Aryl chloroethylureas (CEUs) are potent anti-neoplastic agents alkylating specific intracellular proteins such as βII-tubulin. Recently we have identified a new subset of CEU derived from compound 36 that alkylates thioredoxin isoform 1 (Trx-1), inhibits the nuclear translocation of Trx-1, and favors the accumulation of cells in G0/G1 phase. We have evaluated the effects of various substituents and their position on the aromatic ring of a series of derivatives of 36 on (i) the anti-proliferative activity, (ii) the cell cycle progression, (iii) the nuclear translocation of Trx-1, and (iv) their covalent binding to β-tubulin. The same experiments were performed on representative CEU derivatives where the 2-chloroethyl amino moiety is replaced by either an ethyl, a 2-aminooxazolinyl or a 2-chloroacetyl group. On one hand, our results suggest that CEUs substituted on the phenyl ring at position 3 or 4 by cycloalkyl and substituted cycloalkyl or cycloalkoxy groups inhibit the nuclear translocation of Trx-1 and arrest the cell cycle progression in G0/G1. On the other hand, CEUs substituted by a fused aromatic ring, an aliphatic chain, or a fused aliphatic ring are alkylating βII-tubulin but not Trx-1. Beside the expected inactivity of the ethylurea derivatives, none of the modification to the electrophilic moiety led to cross-selectivity of the drugs toward β-tubulin but increased the anti-proliferative activity and resulted in mitigated effects on Trx-1 translocation.

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.

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.