622-58-2

Usage

Uses

Used in Chemical Synthesis:
p-Tolyl isocyanate is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its reactivity allows it to undergo a wide range of chemical reactions, such as nucleophilic addition, substitution, and rearrangement, making it a versatile building block in organic chemistry.
Used in Catalyst Research:
p-Tolyl isocyanate has been employed in the study of catalytic processes, particularly in the investigation of the catalytic role of supported Rhodium(I) complexes. In the provided material, it was used to study the reductive carbonylation of nitrobenzene in DMF (dimethylformamide) medium. This research helps in understanding the catalytic properties of metal complexes and their potential applications in various chemical transformations.
Used in Polymer Industry:
Although not explicitly mentioned in the provided materials, p-Tolyl isocyanate can also be used in the polymer industry as a monomer for the synthesis of polyurethanes and other polymeric materials. Its ability to form urethane linkages with alcohols and amines makes it a valuable component in the production of polymers with specific properties, such as flexibility, durability, and thermal stability.

InChI:InChI=1/C8H7NO/c1-7-2-4-8(5-3-7)9-6-10/h2-5H,1H3

Upstream product

• 75-44-5 phosgene 
• 540-23-8 p-toluidine hydrochloride 
• 28643-58-5 benzyl-p-tolyl-carbamoyl chloride 
• 622-51-5 p-tolylurea 
• 121781-91-7 S-ethyl N-(4-methylphenyl)thiocarbamate 
• 2327-67-5 N-(p-tolyl)-P,P,P-triphenylphosphine imide 
• 15719-64-9 methylammonium carbonate 
• 92858-52-1 (4-methyl-α-nitro-benzylidene)-phthalide 
• 106-49-0 p-toluidine 
• 7625-64-1 p-tolyl-carbamic acid benzyl ester 
• 141-43-5 ethanolamine 
• 5255-66-3 ethyl p-tolylcarbamate 
• 17574-84-4 1-methoxy-2-methylprop-1-ene 
• 22693-32-9 4-methylbenzoyl azide 

Downstream Products

• 58030-64-1 1-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)-3-p-tolyl-urea 
• 6849-99-6 5-p-tolylcarbamoyloxy-benzo[1,3]dioxole 
• 109558-38-5 N-(4-amino-2-methyl-[6]quinolyl)-N'-p-tolyl-urea 
• 89609-46-1 1-(4-methylphenyl)-3-cyclohexylurea 
• 621-00-1 1,3-di-p-tolylurea 
• 3815-63-2 3-(4-chlorophenyl)-1-(4-tolyl)urea 
• 110396-98-0 p-tolyl-carbamic acid-((S)-2-methyl-butyl ester) 
• 55021-30-2 N-p-tolylcarbamoyl-L-methionine 
• 459-15-4 p-tolyl-carbamic acid-(2-fluoro-ethyl ester) 
• 537-83-7 2,2,2-trifluoroethyl p-tolylcarbamate 

Relevant academic research and scientific papers

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

Design, synthesis and structure-activity relationship study of novel urea compounds as FGFR1 inhibitors to treat metastatic triple-negative breast cancer

Triple-negative breast cancer (TNBC) is an aggressive type of cancer characterized by higher metastatic and reoccurrence rates, where approximately one-third of TNBC patients suffer from the metastasis in the brain. At the same time, TNBC shows good responses to chemotherapy, a feature that fuels the search for novel compounds with therapeutic potential in this area. Recently, we have identified novel urea-based compounds with cytotoxicity against selected cell lines and with the ability to cross the blood-brain barrier in vivo. We have synthesized and analyzed a library of more than 40 compounds to elucidate the key features responsible for the observed activity. We have also identified FGFR1 as a molecular target that is affected by the presence of these compounds, confirming our data using in silico model. Overall, we envision that these compounds can be further developed for the potential treatment of metastatic breast cancer.

Insecticidal sterilization composition and application thereof

The insecticidal sterilization composition comprises the following raw materials in parts by weight 1 - 50% parts of isopyrazam, 1 - 40% parts of trichloroisocyanuric acid, 1 - 2% parts of synergist and the balance of excipients. By compounding isothiopham and trichloroisocyanuric acid, the effects are complementary, the bactericidal spectrum is wider, and the bactericidal activity is high. Under the action of the initiator A I BN, the intermediate 5, the intermediate 6 and the acrylamide are polymerized to obtain a synergist which is a water-soluble compound and is grafted with a hindered amine structure, a benzophenone structure and a benzisothiazolinone structure.

Discovery of BMS-986235/LAR-1219: A Potent Formyl Peptide Receptor 2 (FPR2) Selective Agonist for the Prevention of Heart Failure

Formyl peptide receptor 2 (FPR2) agonists can stimulate resolution of inflammation and may have utility for treatment of diseases caused by chronic inflammation, including heart failure. We report the discovery of a potent and selective FPR2 agonist and its evaluation in a mouse heart failure model. A simple linear urea with moderate agonist activity served as the starting point for optimization. Introduction of a pyrrolidinone core accessed a rigid conformation that produced potent FPR2 and FPR1 agonists. Optimization of lactam substituents led to the discovery of the FPR2 selective agonist 13c, BMS-986235/LAR-1219. In cellular assays 13c inhibited neutrophil chemotaxis and stimulated macrophage phagocytosis, key end points to promote resolution of inflammation. Cardiac structure and functional improvements were observed in a mouse heart failure model following treatment with BMS-986235/LAR-1219.

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.

Design, synthesis and antitumor assessment of phenylureas bearing 5-fluoroindolin-2-one moiety

Background: The development of novel antineoplastic agents remains highly desirable. Objective: This study focuses on the design, synthesis, and antitumor evaluation of phenyl ureas bearing 5-fluoroindolin-2-one moiety. Methods: Three sets of phenylureas were designed and synthesized and their antiproliferative abil-ity was measured against four human carcinoma cell lines (Hela, Eca-109, A549, and MCF-7) via MTT assay. In vivo anticancer activity was further evaluated in xenograft models of human breast cancer (MCF-7). Results: A total of twenty-one new compounds were synthesized and characterized by means of1 H and13 C NMR as well as HR-MS. Three sets of compounds (1a?1c, 2a?2c, and 3a?3c) were ini-tially constructed, and preliminary antiproliferative activities of these molecules were evaluated against Hela, Eca-109, A549 and MCF-7, highlighting the meta-substituted phenylureas (1a?1c) as the most cytotoxic set. A series of meta-substituted phenylureas derivatives (1d?1o) were then designed and synthesized for structure-activity relationship study. Most of the new compounds showed desirable cytotoxicity, among which compound 1g exhibited the most remarkable cyto-toxic effects against the tested human cancer cells with IC50 values ranging from 1.47 to 6.79 μM. Further studies showed that compound 1g suppressed tumor growth in human breast cancer (MCF-7) xenograft models without affecting the body weight of its recipients. Conclusion: In this study, twenty-one new compounds, containing the privileged structures of phenylurea and 5-fluoroindolin-2-one, were designed and synthesized. Subsequent structure-activity studies showed that 1g was the most bioactive antitumor agent among all tested com-pounds, hence a potentially promising lead compound once given further optimization.

One stone two birds: Cobalt-catalyzed in situ generation of isocyanates and benzyl alcohols for the synthesis of N-aryl carbamates

An efficient method for the synthesis of N-aryl carbamates from N-Boc-protected amines has been developed. The cobalt-catalyzed in situ generation of isocyanates from N-Boc-protected amines and benzyl alcohols from benzyl formates has been achieved for the first time, which in turn furnished the corresponding benzyl carbamates in moderate to high yields. The reaction was catalyzed by CoI2 with tris-(4-dimethylaminophenyl)-phosphine as the ligand and zinc powder as the reductant. The developed reaction conditions were found to be compatible for aromatic amines with both electron-donating and -withdrawing substituents.

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.

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.

Isothiazolinone compound and corresponding application

The invention provides an isothiazolinone compound with an IDO inhibitory activity, and a preparing method and pharmaceutical application thereof. The invention particularly relates to a compound shown in a formula I, pharmaceutically acceptable salts thereof, isomers and prodrugs, wherein definitions of all groups are shown in the description. The invention further relates to compound drug preparations, drug compositions and the application of the compound drug preparations and the drug compositions in treating, relieving and/or preventing various relevant diseases caused by immunosuppressionsuch as tumors, virus infection or autoimmune diseases. The isothiazolinone compound has the excellent IDO inhibitory activity.