37527-66-5

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dimethoxyphenyl isocyanate is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to react with other molecules to form a wide range of biologically active substances. Its reactivity allows for the creation of new drugs with potential applications in treating different diseases.
Used in Chemical Synthesis:
In the chemical industry, 3,4-dimethoxyphenyl isocyanate is used as a building block for the synthesis of various organic compounds, including dyes, pigments, and polymers. Its unique chemical structure allows for the development of novel materials with specific properties tailored for different applications.
Used in Research and Development:
3,4-Dimethoxyphenyl isocyanate is utilized as a research compound in academic and industrial laboratories for studying its chemical properties and potential applications. Its reactivity and structural features make it an interesting candidate for exploring new reaction pathways and developing innovative synthetic methods.
Used in Agrochemical Industry:
3,4-Dimethoxyphenyl isocyanate is employed as a starting material for the development of agrochemicals, such as pesticides and herbicides. Its unique chemical structure can be modified to create new active ingredients with improved efficacy and selectivity, contributing to more sustainable agricultural practices.
Used in Coatings and Adhesives:
In the coatings and adhesives industry, 3,4-dimethoxyphenyl isocyanate is used as a component in the formulation of polyurethane-based products. Its isocyanate functionality allows for the creation of durable and high-performance materials with excellent adhesion properties and resistance to various environmental factors.

InChI:InChI=1/C9H9NO3/c1-12-8-4-3-7(10-6-11)5-9(8)13-2/h3-5H,1-2H3

Upstream product

• 75-44-5 phosgene 
• 6315-89-5 3,4-dimethoxyaniline 
• 40926-90-7 3,4-dimethoxybenzoyl azide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 93-07-2 Veratric acid 

Downstream Products

• 106107-52-2 methyl (3,4-dimethoxyphenyl)carbamate 
• 106107-51-1 ethyl (3,4-dimethoxyphenyl)carbamate 
• 65141-27-7 N-(3,4-dimethoxyphenyl)-O-phenyl carbamate 

Relevant academic research and scientific papers

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.

Synthetic method for 2-chloro-4-amino-6,7-dimethoxy quinazoline

The invention discloses a synthetic method for 2-chloro-4-amino-6,7-dimethoxy quinazoline. The synthetic method comprises the following steps: 1) preparing 3,4-dimethoxyphenyl isocyanate; 2) preparing 3,4-dimethoxyphenyl cyanourea; 3) preparing a 2-chloro-4-amino-6,7-dimethoxy quinazoline crude product; and 4) preparing a 2-chloro-4-amino-6,7-dimethoxy quinazoline fine product. The synthetic method disclosed by the invention simplifies reaction steps and increases the product yield; reaction conditions are optimized, so that reactants react more sufficiently, and therefore, generation of byproducts is reduced, production efficiency is improved, reactants are prevented from being oxidized, reaction is more complete, the target object can be obtained by direct filtering and drying during post-treatment, and the yield is stable.

Copper-catalyzed N[sbnd]H/S[sbnd]H functionalization: A strategy for the synthesis of benzothiadiazine derivatives

A copper-mediated N[sbnd]S bond-forming reaction via N[sbnd]H/S[sbnd]H activation is described. This reaction occurs under mild conditions with high efficiency, step economy, and tolerates a wide variety of functional groups, providing an efficient means of accessing biologically important 1,2,4-benzothiadiazin-3(4H)-ones.

Substituted 1,2,3,4-tetrahydrobenzo[C][2,7] naphthyridines and derivatives thereof as kinase inhibitors

The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.

Dipeptidyl peptidase inhibitors for the preparation of iodo, chloro, iodo intermediate and method

The invention provides an iodination preparation method for a dipeptidyl peptidase inhibitor, chlorination and iodination intermediates of the dipeptidyl peptidase inhibitor and preparation methods for the intermediates. According to the invention, an intermediate chlorinated compound is subjected to iodination in an organic solvent, and then a compound represented by a formula I and a salt thereof are prepared from an iodinated compound and used as the dipeptidyl peptidase inhibitor, wherein in the formula 1 descried in the invention, R1 is selected from an aryl group, a heteroaryl group and an alkyl group, or from an aryl group, a heteroaryl group and an alkyl group substituted by an alkyl or alkoxy group whose substituent groupp has a carbon atom number of C1 to C8, and X is an alkylene group with a carbon atom number of C1 to C8. Compared with conventional methods which prepare the compound represented by the formula I from brominated compounds, the method provided by the invention has the advantages of a substantial increase in yield and no need for column chromatographic purification, thereby facilitating industrial synthesis.

Reductive amination of dipeptidyl peptidase inhibitors for the preparation method, intermediate and method

The invention provides a reductive amination preparation method for a dipeptidyl peptidase inhibitor, intermediate ester, alcohol and aldehyde compounds used for preparation of the dipeptidyl peptidase inhibitor and preparation methods for the intermediates. According to the invention, an ester compound is produced from an intermediate chlorinated compound in an organic solvent and is then hydrolyzed to obtain alcohol, the alcohol is oxidized to obtain aldehyde, and then a compound represented by a formula I is prepared from an aldehyde compound through reductive amination, wherein in the formula 1 descried in the invention, R1 is selected from an aryl group, a heteroaryl group and an alkyl group, or from an aryl group, a heteroaryl group and an alkyl group substituted by an alkyl or alkoxy group whose substituent group has a carbon atom number of C1 to C8, and X is an alkylene group with a carbon atom number of C1 to C8. Compared with conventional methods which prepare the compound represented by the formula I from brominated compounds, the method provided by the invention has the advantages of a substantial increase in yield, great improvement of stability of the compound represented by the formula I and no need for column chromatographic purification, thereby facilitating industrial synthesis.

Novel VEGFR-2 kinase inhibitors identified by the back-to-front approach

We report a novel VEGFR-2 inhibitor, developed by the back-to-front approach. Docking experiments indicated that the 3-chloromethylphenylurea motif of the lead compound occupied the back pocket of VEGFR-2 kinase. An attempt was made to enhance the binding affinity of 1 by expanding the structure to access the front pocket using a triazole linker. A library of 1,4-(disubstituted)-1H-1, 2,3-triazoles were screened in silico, and one compound (VH02) was identified with an IC50 against VEGFR-2 of 0.56 μM. VH02 showed antiangiogenic effects, inhibiting tube formation in HUVEC cells (EA.hy926) at 0.3 μM, 13 times lower than its cytotoxic dose. These enzymatic and cellular activities suggest that VH02 has potential as a lead for further optimization.

Discovery and structural modification of 1-phenyl-3-(1-phenylethyl)urea derivatives as inhibitors of complement

A series of 1-phenyl-3-(1-phenylethyl)urea derivatives were identified as novel and potent complement inhibitors through structural modification of the original compound from high-throughput screening. Various analogues (7 and 13-15) were synthesized and identified as complement inhibitors, with the introduction of a five- or six-carbon chain (7c, 7d, 7k, 7l, and 7o) greatly improving their activity. Optimized compound 7l has an excellent inhibition activity with IC50 values as low as 13 nM. We demonstrated that the compound 7l inhibited C9 deposition through the classical, the lectin, and the alternative pathways but had no influence on C3 and C4 depositions.

Synthesis and evaluation of structurally constrained imidazolidin derivatives as potent dipeptidyl peptidase IV inhibitors

To find potent and selective inhibitors of dipeptidyl peptidase IV (DPP-IV), we synthesized a series of 2-cyanopyrrolidine derivatives with constrained imidazolidin ring and tested their activities against DPP-IV. Most of them exhibited submicromolar inhibitory activities against DPP-IV. The most potent compound among these is (S)-1-(2-(2-(3-(3,4-dimethoxyphenyl)-2-oxoimidazolidin-1-yl)ethyl-amino)acetyl)pyrrolidine-2-carbonitrile (6n), which is a 2 nM DPP-IV inhibitor.

Synthesis of 4-benzyliden-2-oxazolidinone derivatives via gold-catalyzed intramolecular hydroamination

AuCl-catalyzed intramolecular hydroamination of N-aryl-O-propargyl carbamates (3) efficiently affords (Z)-N-aryl-4-benzyliden-2-oxazolidinones (4) via a 5-exo dig cyclization. The reaction proceeds in acetonitrile at 60 °C and requires tBuOK or KOH as a base co-catalyst. It tolerates the presence of multiple substituted aryl units with electron donating methoxy groups. The method opens a convenient, flexible and operationally simple access to a new class of twisted molecules with potentially interesting biological properties.