56309-56-9

Usage

Uses

2-Isopropylphenyl isocyanate is used as intermediates.

InChI:InChI=1/C10H11NO/c1-8(2)9-5-3-4-6-10(9)11-7-12/h3-6,8H,1-2H3

Upstream product

• 124-38-9 carbon dioxide 
• 2446-83-5 di-isopropyl azodicarboxylate 
• 643-28-7 2-isopropylaniline 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 75-44-5 phosgene 
• 851199-82-1 2-isopropylphenyl trifluoromethanesulfonate 
• 917-61-3 sodium isocyanate 
• 88-69-7 2-(1-methylethyl)phenol 

Downstream Products

• 38103-25-2 1-{[(E)-4-Chloro-2-methyl-phenylimino]-methyl}-3-(2-isopropyl-phenyl)-1-methyl-urea 
• 23122-33-0 C₁₈H₂₀N₂O₄ 
• 38008-54-7 (2-Isopropyl-phenyl)-carbamic acid 3-methylsulfanylcarbonylamino-phenyl ester 
• 128255-24-3 (2-Isopropyl-phenyl)-carbamic acid 2-piperidin-1-yl-ethyl ester; hydrochloride 
• 124420-85-5 1-(2-Isopropyl-phenyl)-3-pyridin-4-yl-urea 
• 131449-95-1 (S)-3-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-6-[3-(2-isopropyl-phenyl)-ureido]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid 
• 1098477-89-4 1-(2-hydroxy-4-nitrophenyl)-3-(2-isopropylphenyl)urea 
• 1260072-97-6 4-{([(2'-isopropylphenyl)amino]carbonyl)amino}benzenesulfonamide 

Relevant academic research and scientific papers

COMPOUNDS, COMPOSITIONS, AND METHODS FOR SELECTIVELY INHIBITING β-GLUCURONIDASES AND ALLEVIATING SIDE EFFECTS ASSOCIATED WITH DRUG TREATMENT INDUCED DIARRHEA

The present disclosure describes compounds and compositions that inhibit β-glucuronidase activity, and methods for attenuating the side effects of one or more drugs and improving the efficacy of drugs by administration of selective β-glucuronidase inhibitors.

Palladium-catalyzed synthesis of N-aryl carbamates

An efficient synthesis of aryl carbamates was achieved by introducing alcohols into the reaction of palladium-catalyzed cross-coupling of ArX (X = Cl, OTf) with sodium cyanate. The use of aryl triflates as electrophilic components in this transformation a

A simple and efficient synthesis of diaryl ureas with reduction of the intermediate isocyanate by triethylamine

Thirty symmetrical diaryl urea derivatives were synthesised in moderate to excellent yields from arylamine and triphosgene with triethylamine as a reducing agent for the intermediate, isocyanate. It was significant that part of the products could be collected in almost quantitative yield without column chromatography. The procedure under mild reaction conditions was tolerant of a wide range of functional groups. The structures of the compounds were determined by NMR, MS and X-ray crystallographic analyses.

Structural optimization of a CXCR2-directed antagonist that indirectly inhibits γ-secretase and reduces Aβ

Amyloid β (Aβ), a key molecule in the pathogenesis of Alzheimer's disease (AD), is derived from the amyloid precursor protein (APP) by sequential proteolysis via β- and γ-secretases. Because of their role in generation of Aβ, these enzymes have emerged as important therapeutic targets for AD. In the case of γ-secretase, progress has been made towards designing potent inhibitors with suitable pharmacological profiles. Direct γ-secretase inhibitors are being evaluated in clinical trials and new strategies are being explored to block γ-secretase activity indirectly as well. In this regard, we have previously reported an indirect regulation of γ-secretase through antagonism of CXCR2, a G-protein coupled receptor (GPCR). We demonstrated that N-(2-hydroxy-4-nitrophenyl)-N′-(2-bromophenyl)urea (SB225002), a selective inhibitor of CXCR2 also plays a role in an indirect inhibition of γ-secretase. Furthermore, we reported a ～5-fold difference in the selective inhibition of APP versus Notch processing via γ-secretase following treatment with SB225002. Herein we describe the synthesis and optimization of SB225002. By determination of the structure-activity relationship (SAR), we derived small molecules that inhibit Aβ40 production with IC50 values in the sub-micromolar range in a cell-based assay and also validated the potential of CXCR2 as a new target for therapeutic intervention in AD.

A facile method for preparation of aromatic isocyanates using bis(trichloromethyl)carbonate

A facile synthesis of aromatic isocyanates using bis(trichloromethyl)carbonate (BTC) is reported with high yields of products. BTC is used to supply phosgene in situ in stoichiometric amounts.

Preparation of isocyanates from primary amines and carbon dioxide using Mitsunobu chemistry

Primary alkylamines 1 and hindered arylamines 1 give high yields of isocyanates 5 when reacted with carbon dioxide and the Mitsunobu zwitterions 4 generated from dialkyl azodicarboxylates and Bu3P in dichloromethane at - 78°C. Use of Ph3P still gave high yields of isocyanates from reactions of primary alkylamines, but only low yields were obtained from reactions of aromatic amines. Reactions which failed to give high yields of isocyanates gave either carbamoylhydrazines 6 and/or dicarbamoylhydrazines 10 and/or triazolinones 7. The triazolinones were shown to arise from reactions of reactive aryl isocyanates with the Mitsunobu zwitterion. The carbamoylhydrazines were shown not to arise from reaction of isocyanate with reduced dialkyl azodicarboxylates, and a mechanism for their formation is proposed. Single-crystal X-ray analyses confirmed the structures of 6, 7, and 10.