1793-07-3

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(METHOXYCARBONYL)PHENYL ISOCYANATE is used as a key intermediate for the synthesis of various pharmaceutical compounds, including 3H-quinazolin-4-ones, which are known for their potential therapeutic properties.
Used in Biochemical Research:
In the field of biochemical research, 2-(METHOXYCARBONYL)PHENYL ISOCYANATE is used as a starting material for the synthesis of A1120, a high affinity (Ki = 8.3nM) non-retinoid ligand for the Retinol-binding protein. 2-(METHOXYCARBONYL)PHENYL ISOCYANATE plays a crucial role in understanding the binding mechanisms and potential applications in drug development.
Used in Agrochemical Industry:
2-(METHOXYCARBONYL)PHENYL ISOCYANATE is also used in the agrochemical industry for the synthesis of transand cis-N-phenyl-N′-(4-phenoxy)cyclohexylureas. These compounds exhibit potential bioactivity and can be used as pesticides or herbicides, contributing to the development of more effective and environmentally friendly agricultural solutions.

InChI:InChI=1/C9H7NO3/c1-13-9(12)7-4-2-3-5-8(7)10-6-11/h2-5H,1H3

Upstream product

• 4376-18-5 Monomethyl phthalate 
• 75-44-5 phosgene 
• 134-20-3 2-carbomethoxyaniline 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 23122-05-6 2-(3-Methoxycarbonylamino-phenoxycarbonylamino)-benzoic acid methyl ester 
• 118-48-9 isatoic anhydride 
• 21282-62-2 methyl 2-(morpholine-4-carboxamido)benzoate 
• 128255-26-5 2-(2-Piperidin-1-yl-ethoxycarbonylamino)-benzoic acid methyl ester; hydrochloride 
• 110919-50-1 2-<((5-amino-1H-tetrazol-1-yl)carbonyl)amino>benzoic acid methyl ester 
• 104728-09-8 N-2'-carbomethoxy-2-oxo-3,4,5,6-tetrahydrobenzanilide 
• 104728-10-1 N-2'-carbomethoxy-2-morpholino-3,4,5,6-tetrahydrobenzanilide 
• 100076-25-3 methyl 2-(3-sec-butylureido)benzoate 
• 117679-21-7 2-[(1-Oxo-1,2-dihydro-benzo[d]azepine-3-carbonyl)-amino]-benzoic acid methyl ester 
• 100076-42-4 2-[3-(1-Methoxycarbonyl-3-methyl-butyl)-ureido]-benzoic acid methyl ester 
• 100076-42-4 2-[3-((R)-1-Methoxycarbonyl-3-methyl-butyl)-ureido]-benzoic acid methyl ester 
• 100076-42-4 2-[3-((S)-1-Methoxycarbonyl-3-methyl-butyl)-ureido]-benzoic acid methyl ester 
• 100075-59-0 2-(3-Hexyl-ureido)-benzoic acid methyl ester 
• 100076-47-9 2-[3-(3-Ethoxycarbonyl-propyl)-ureido]-benzoic acid methyl ester 

Relevant academic research and scientific papers

A practical solid phase synthesis of quinazoline-2, 4-diones

We describe a practical solid phase synthesis of quinazoline-2,4-diones using a short-chain, high loading capacity, polyethyleneglycol polystyrene copolymer ('PEG4-PS' resin). The highlights of this synthesis include efficient acyl azide format

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)

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.

Quinazolinedione sulfonamides: A novel class of competitive AMPA receptor antagonists with oral activity

Quinazoline-2,4-diones with a sulfonamide group attached to the N(3) ring atom constitute a novel class of competitive AMPA receptor antagonists. One of the synthesized compounds, 28, shows nanomolar receptor affinity, whereas other examples of the series display oral anticonvulsant activity in animal models.

Discovery of orally bioavailable and novel urea agonists of the high affinity niacin receptor GPR109A

A urea class of high affinity niacin receptor agonists was discovered. Compound 1a displayed good PK, better in vivo efficacy in reducing FFA in mouse than niacin, and no vasodilation in a mouse model. Compound 1q demonstrated equal affinity to GPR109A as niacin.

Organosilicon synthesis of isocyanates: III. Synthesis of aliphatic, carbocyclic, aromatic, and alkylaromatic isocyanatocatboxylic acid esters

A series of aminoacid esters was prepared by treating the aminoacid suspensions in ethanol with thionyl chloride. Best conversion of aminoacid esters to corresponding isocyanates was achieved in the case of aromatic and carbocyclic aminoesters by phosgeneation of their N-silyl derivatives, and in the case of aliphatic and alkylaromatic aminoesters by phosgeneation of O-silyl or N,O-bissilylurethanes on their basis. In the last case additional step of esterification of the by-products isocyanatoalkylcarboxylic acid chlorides is required after phosgeneation. Unusual generation of cynnamates and intramolecular N→O-migration of trimethylsilyl group in the solutions of silylated alkylaromatic β-aminoacid esters were found. Pleiades Publishing, Inc., 2006.

SYNTHESIS OF PROTECTED PYRROLOBENZODIAZEPINES

A method of synthesis of a N-10 protected PBD compound of formula (I) via an intermediate of formula (II) or formula (V).

New phenylalanine derivatives

Specified phenylalanine derivatives and analogues thereof have an antagonistic activity to α4 integrin. They are used as therapeutic agents for various diseases concerning α4 integrin.

2-amino-4H-3,1-benzoxazin-4-ones as inhibitors of C1r serine protease

A series of 2-amino-4H-3,1-benzoxazin-4-ones have been synthesized and evaluated as inhibitors of the complement enzyme C1r. C1r is a serine protease at the beginning of the complement cascade, and complement activation by β-amyloid may represent a major contributing pathway to the neuropathology of Alzheimer's disease. Compounds such as 7-chloro-2-[(2- iodophenyl)amino]benz[d][1,3]oxazin-4-one (32) and 7-methyl-2-[(2- iodophenyl)amino]benz[d][1,3]oxazin-4-one (37) show improved potency compared to the reference compound FUT-175. Many of these active compounds also possess increased selectivity for C1r compared to trypsin and enhanced hydrolytic stability relative to 2-(2-iodophenyl)-4H-3,1-benzoxazin-4-one (1).

Quinaldoyl-amine derivatives of oxo-and hydroxy-substituted hydrocarbons

The present invention discloses the compounds of general formula (1) STR1 wherein R1, R2, R3 are optionally substituted carbonyl and amide derivatives which are useful as inhibitors of retroviral proteases, and are effecti