3320-83-0

Usage

Uses

Used in Photocatalytic Degradation Studies:
2-Chlorophenyl isocyanate is used as a standard to investigate the photocatalytic degradation of Monuron over TiO2 suspensions. In this application, it serves as a reference compound to evaluate the efficiency of the photocatalytic process in breaking down harmful pollutants, such as Monuron, a widely used herbicide.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-Chlorophenyl isocyanate is used in the preparation of 2-(2-chlorophenylamino)-3,5-dihydro-5,5-dimethyl-3-phenyl-6H-imidazo[1,2-b]-1,2,4-triazol-6-one. 2-Chlorophenyl isocyanate is a potential candidate for the development of new drugs, as it possesses a unique chemical structure that can be further modified to target specific biological pathways.
Used in Chemical Synthesis:
2-Chlorophenyl isocyanate is also utilized in the synthesis of pentenylated β-cyclodextrin chlorophenyl carbamates. These compounds are of interest in various fields, including agriculture and materials science, due to their potential applications as additives, stabilizers, or functional components in the development of new products.
Overall, 2-Chlorophenyl isocyanate is a valuable chemical intermediate with diverse applications across different industries, including environmental protection, pharmaceuticals, and materials science. Its unique chemical properties and reactivity make it an essential component in the development of new compounds and technologies.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C7H4ClNO/c8-6-3-1-2-4-7(6)9-5-10/h1-4H

Upstream product

• 53821-00-4 benzyl (2-chlorophenyl)carbamate 
• 141-43-5 ethanolamine 
• 75-44-5 phosgene 
• 95-51-2 o-chloroaniline 
• 201230-82-2 carbon monoxide 
• 88-73-3 2-Chloronitrobenzene 
• 137-04-2 2-chloroaniline hydrochloride 
• 168481-89-8 3,4-bis(2-chlorophenyl)-1,2,5-oxadiazole 2-oxide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 2905-23-9 2-chlorophenylsulfonyl chloride 
• 17512-69-5 2-chlorophenylhydroxamic acid 
• 609-66-5 2-chlorobenzamide 
• 530-62-1 1,1'-carbonyldiimidazole 
• 118-91-2 ortho-chlorobenzoic acid 

Downstream Products

• 105908-83-6 N-(2-chlorophenyl)morpholine-4-carboxamide 
• 107149-87-1 (2-chloro-phenyl)-carbamic acid-(2-morpholino-ethyl ester) 
• 100709-64-6 N-(2-chloro-phenyl)-N'-(4,5,6,7-tetrahydro-benzothiazol-2-yl)-urea 
• 108897-92-3 (2-chloro-phenyl)-carbamic acid-(5-methyl-2-phenyl-2H-pyrazol-3-yl ester) 
• 20668-13-7 methyl N-(2-chlorophenyl)carbamate 
• 108871-74-5 (2-chloro-phenyl)-peroxycarbamic acid tert-butyl ester 
• 99585-05-4 N'-(2-chloro-phenyl)-N-formyl-N-methyl-urea 
• 4835-22-7 (2-chloro-phenyl)-carbamic acid-(4-chloro-but-2-ynyl ester) 
• 103859-14-9 (2-chloro-phenyl)-carbamic acid-(2-dimethylamino-ethyl ester) 
• 5255-70-9 ethyl N-(o-chlorophenyl) carbamate 
• 102007-94-3 N-(2-chloro-phenyl)-N'-(2-diethylamino-ethyl)-N'-phenyl-urea 
• 99513-97-0 (2-chloro-phenyl)-carbamic acid-(4-chloro-phenyl ester) 
• 582-44-5 3-(2-chlorophenyl)-1,1-dimethylurea 
• 10129-32-5 (2-chloro-phenyl)-thiocarbamic acid S-isopropyl ester 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus

Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78–22.4 μM) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization.

Sulfonylurea dehydroabietate compound and preparation method and application thereof

The invention discloses a sulfonylurea dehydroabietate compound and a preparation method and application thereof. The compound has a chemical structural formula represented by a formula shown in the description, wherein R1 is 2-Br, 3-Br, 4-Br, 4-OCH3, 4-F, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl or H, and 2, 3 and 4 represent 2, 3 and 4 substituent sites on a benzene ring. The preparation method of the compound comprises the following steps synthesizing sulfonyl chloride dehydroabietate; synthesizing sulfonamide dehydroabietate; synthesizing substituted phenyl isocyanate; synthesizing N'-substituted phenyl-12-sulfonylurea dehydroabietate. The compound disclosed by the invention has better activity and low toxicity and provides a better lead compound for developing antitumor drugs.

Design, synthesis, and biological evaluation of tetrahydroisoquinoline-based diaryl urea derivatives for suppressing VEGFR-2 signaling

A novel structural series of tetrahydroisoquinoline-based compounds that incorporate the diaryl urea moiety was designed, synthesized, and biologically evaluated as suppressors of VEFGR-2 signaling. As a consequence, compounds 9k and 9s exhibited comparable or superior cytotoxic activity to that of gefitinib against the tested three cell lines, including A549, MCF-7, and PC-3. Importantly, both of them downregulated the expression of VEGFR-2, and inhibited VEGFR-2 phosphorylation at the concentration of 0.5 or 1.0 μmol/l. Besides, they suppressed human umbilical vein endothelial cell tube formation at the concentration of 4.0 μmol/l. Considering their capability of down-regulating VEGFR-2 expression and inhibiting VEGFR-2 phosphorylation, 9k and 9s may serve as suppressors of angiogenesis for further investigation.

Design, synthesis and structure-activity relationship of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure as multi-target inhibitors against receptor tyrosine kinase

Inspired by that the multi-target inhibitors against receptor tyrosine kinases (RTKs) have significantly improved the effect of clinical treatment for cancer, and based on the chemical structure of Linifanib (ABT-869, Abbott), two series of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure were designed and synthesized as multi-target inhibitors against RTKs. The preliminary biological evaluation showed that several compounds exhibited comparable potency with Linifanib. Compound S21 was identified as the most potent inhibitor against Fms-like tyrosine kinase 3 (FLT-3), kinase insert domain containing receptor (KDR) and platelet-derived growth factor receptor β (PDGFR-β) with its IC50 values were 4 nM, 3 nM and 8 nM respectively, it also showed potent inhibitory activities against several cancer cells.

Phenylquinoline transient receptor potential vanilloid 1 antagonists for the treatment of pain: Discovery of 1-(2-phenylquinoline-4-carbonyl)-N-(4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide

Reported herein is the design, synthesis, and pharmacologic characterization of a class of TRPV1 antagonists constructed on a phenylquinoline platform that evolved from Cinchophen lead. This design composes three sections: a phenylquinoline headgroup attached to an aliphatic carboxamides, which is tethered at a phenyl tail group. Optimization of this design led to the identification of 37, comprising a pyrrolidine linker and a trifluoromethyl–phenyl tail. In the TRPV1 functional assay, using cells expressed hTRPV1, 37 antagonized capsaicin-induced Ca2+ influx, with an IC50 value of 10.2 nM. In the complete mice analgesic model, 37 exhibited better antinociceptive activity than the positive control BCTC in diverse pain models. All of these results suggested that 37 could be considered as a lead candidate for the further development of antinociceptive drugs.

Discovery of novel anti-angiogenesis agents. Part 8: Diaryl thiourea bearing 1H-indazole-3-amine as multi-target RTKs inhibitors

VEGFR-2, TIE-2, and EphB4 are essential for both angiogenesis and tumorigenesis. Herein, we designed and prepared three classes of multi-target inhibitors based on the extensive sequence homology along the kinase domain of angiogenic RTKs. Biological evaluation indicated that these multi-target inhibitors exhibited considerable potential as novel anti-angiogeneic and anticancer agents. Among them, a diaryl thiourea bearing 1H-indazole-3-amine (16a) displayed the most potent RTK inhibition and excellent selectivity. It also showed inhibition on viability of human umbilical vein endothelial cells and anti-proliferation against a broad spectrum of cancer cells. Therefore, 1H-indazole-3-amine could serve as a promising hinge binding group for multi-target inhibitors of VEGFR-2, Tie-2, and EphB4.

Discovery of novel anti-angiogenesis agents. Part 7: Multitarget inhibitors of VEGFR-2, TIE-2 and EphB4

Herein, we embarked on a structural optimization campaign aiming at the discovery of second generation anti-angiogenesis agents with our previously reported BPS-7 as lead compound. A library of 27 compounds has been afforded based on the highly conserved ATP-binding pocket of VEGFR-2, Tie-2, and EphB4. Several title compounds exhibited simultaneous inhibitory effects against three angiogenic RTKs. These compounds with a ‘triplet’ inhibition profile have been identified as novel anti-angiogenic and anticancer agents. The representative VDAU11 displayed prominent anti-angiogenic and anticancer potency and could be considered as a candidate for further optimization. These results indicate that N-(pyridin-2-yl)acrylamide could serve as a novel hinge-binding group of triple inhibitors.

Synthesis and antibacterial activity of novel 11-[3-[(arylcarbamoyl)oxy]propylamino]-11-deoxy-6-O-methyl-3-oxoerythromycin A 11-N,12-O-cyclic carbamate derivatives

A series of novel 11-[3-[(arylcarbamoyl)oxy]propylamino]-11-deoxy-6-O-methyl-3-oxoerythromycin A 11-N,12-O-cyclic carbamate derivatives (6a-h) were designed, synthesized and evaluated for their antibacterial activities in vitro. Most of these compounds had significant antibacterial activity against two groups of pathogens of Methicillin-sensitive Staphylococcus aureus (MIC 50 =0.031-2 μg ml -1) except 6g and Methicillin-sensitive S. epidermidis (MIC 50 =0.031-0.5 μg ml -1). MIC 90 of 6d against Methicillin-resistant S. epidermidis was at least 16-fold better than that of erythromycin (EMA), azithromycin (AZM) and ABT-773. 6d and 6e had more potent antibacterial activity against S. pneumoniae than EMA, AZM and ABT-773. In particular, compounds 6d and 6e also showed relatively potent activity against Haemophilus influenzae and Streptococcus hemolyticus.

Design, synthesis, and biological evaluation of novel quinazolinyl-diaryl urea derivatives as potential anticancer agents

Through a structure-based molecular hybridization approach, a series of novel quinazolinyl-diaryl urea derivatives were designed, synthesized, and screened for their in vitro antiproliferative activities against three cancer cell lines (HepG2, MGC-803, and A549). Six compounds (7g, 7m, 7o, 8e, 8g, and 8m) showed stronger activity against a certain cell line compared with the positive reference drugs sorafenib and gefitinib. Among the six compounds, 8g exhibited the strongest activity. In particular, compound 8g induced A549 apoptosis, arrested cell cycle at the G0/G1 phase, elevated intracellular reactive oxygen species level, and decreased mitochondrial membrane potential. This compound can also effectively regulate the expression of apoptosis- and cell cycle-related proteins, and influence the Raf/MEK/ERK pathway. Molecular docking and structure-activity relationship analyses revealed that it can bind well to the active site of the receptor c-Raf, which was consistent with the biological data. Therefore, compound 8g may be a potent antitumor agent, representing a promising lead for further optimization.

With anti-tumor effect of a quinazoline-urea derivative and its application (by machine translation)

The present invention relates to a of the general formula (II) anti-tumor function of said quinazoline-urea derivative and its application. The definition of the substituent in the general formula (II) in the specification. This invention, in order to SUO draw non-Buddhist nun and Geftinat compounds as the precursor, retention of SUO draw non-Buddhist nun the pharmocology-carbamido; at the same time, such as in reserved [...] EGFR-TKIs Geftinat, synthesis, and obtain a series of quinazoline-urea derivatives, by the in vitro activity tests, some compounds exhibit excellent anti-tumor activity, such derivatives have high research and utility value. (II). (by machine translation)