69922-28-7

Usage

Uses

Used in Pharmaceutical Industry:
3,4-(Methylenedioxy)phenyl isocyanate is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs, particularly those targeting specific receptors or enzymes in the body.
Used in Chemical Synthesis:
In the field of organic chemistry, 3,4-(Methylenedioxy)phenyl isocyanate serves as a valuable precursor for the synthesis of a wide range of organic compounds. Its reactivity with various functional groups makes it suitable for creating complex molecules with potential applications in various industries.
Used in Research and Development:
3,4-(Methylenedioxy)phenyl isocyanate is utilized in research laboratories for the exploration of new chemical reactions and the development of innovative synthetic pathways. Its unique properties make it an interesting subject for scientific studies aimed at understanding its reactivity and potential applications.
Used in Agrochemical Industry:
3,4-(Methylenedioxy)phenyl isocyanate may also find applications in the agrochemical sector, where it could be used in the development of new pesticides or herbicides. Its ability to form stable compounds with a variety of structures makes it a promising candidate for creating effective and targeted agrochemicals.
Used in Material Science:
In the realm of material science, 3,4-(Methylenedioxy)phenyl isocyanate could be employed in the design and synthesis of novel materials with specific properties. Its incorporation into polymers or other materials could lead to the development of new products with improved characteristics for various applications.

InChI:InChI=1/C8H5NO3/c10-4-9-6-1-2-7-8(3-6)12-5-11-7/h1-3H,5H2

Upstream product

• 54022-34-3 benzo[d][1,3]dioxole-5-carbonyl azide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 75-44-5 phosgene 
• 94-53-1 Piperonylic acid 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 70156-94-4 benzo[1,3]dioxole-5-carboxylic acid hydroxyamide 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 121809-71-0 2-[4-(3-Benzo[1,3]dioxol-5-yl-ureido)-phenoxy]-2-methyl-propionic acid 
• 34060-22-5 N-methyl-3,4-(methylenedioxy)aniline 
• 1061377-19-2 1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(3-morpholinopropoxy)phenyl)urea 
• 698984-83-7 N-(benzo[d][1,3]dioxol-5-yl)morpholine-4-carboxamide 
• 1374006-37-7 C₁₇H₁₇N₃O₄ 
• 1374006-49-1 C₂₂H₁₉N₃O₄ 

Relevant academic research and scientific papers

Discovery of novel VEGFR-2 inhibitors. Part 5: Exploration of diverse hinge-binding fragments via core-refining approach

Pathological angiogenesis plays a critical role in numerous diseases including malignancy. VEGFR-2 is the central regulators in angiogenesis and has become a promising target for anticancer drug design. We have identified a novel biphenyl-aryl urea incorporated with salicyladoxime (BPS-7) as potent VEGFR-2 inhibitor. As a continuation to our previous research, various aromatic-heterocyclic were introduced as hinge-binding fragment via a core-refining approach. Interestingly, many compounds exhibited comparable VEGFR-2 inhibition to Sorafenib. In particular, 12e and 12o displayed excellent VEGFR-2 inhibitory activity with IC50 values of 0.50 nM and 0.79 nM, respectively. Several title compounds showed considerable antiproliferative activity against A549 and SMMC-7721 cells. In addition, molecular docking was performed to rationalize the efficiency of the better compounds. These results will be instructive for further inhibitor design and optimization.

Carbonyldiimidazole-mediated lossen rearrangement

[Chemical Equation Presented] Carbonyldiimidazole (CDI) was found to mediate the Lossen rearrangement of various hydroxamic acids to isocyanates. This process is experimentally simple and mild, with imidazole and CO 2 being the sole stoichiometric byproduct. Significant for large-scale application, the method avoids the use of hazardous reagents and thus represents a green alternative to standard processing conditions for the Curtius and Hofmann rearrangements.

Synthesis of N-methylphenanthridinone derivatives fused with a silacyclohexane ring by radical reaction using tributyltin hydride

Radical reaction of (N-methyl-7-bromo-2,2-dimethyl-2-silatetralin-6-ylamino)veratramide (8a) and -piperonamides (8b) in boiling benzene using tributyltin hydride and AIBN gave two kinds of N-methylphenanthridinone derivatives (15 and 16), which were cyclized at 6- and 2-positions of aroylic acid moiety. On the other hand, similar reaction of N-methyl-N-(2-bromoveratryl and 2-bromopiperonyl)-2,2-dimethyl-2-silatetralin-6-carboxamides (14) produced N-methylphenanthridinone deivatives (17) as each sole product, in which cyclization occurred at 5-position of 2-silatetralin moiety.

Carbamate compositions and methods fo rmodulating the activity of the CHK1 enzyme

Described herein are carbamate compounds. Such compounds are capable of modulating the activity of a checkpoint kinase, and described herein are methods for utilizing such modulation to treat cell proliferative disorders. Also described are pharmaceutical

Synthesis of new substituted 6-ureidopurines and 6-ureido-9-(2,3,5-triacetyl ribofuranosyl)purines having cytokinin (plant growth promoting) activity

Substituted 6-ureidopurines 6a-j and 6-ureido-9-(2,3,5-triacetylribofuranosyl) purines 7a-j have been synthesized by condensing substituted phenyl isocyanates with adenine 3 and 2,3,5-triacetyladenosine 5 respectively in pyridine. Substituted phenyl isocyanates 2a-j are prepared from substituted anilines 1a-j in the presence of triphosgene and triethylamine in dry benzene. Compounds 6a-j and 7a-j have been evaluated for cytokinin activity on seeds of Raphanus sativus, family Brassicaceae (common name white radish) at 5 different concentrations in distilled water ranging from 0.001 to 10 mg litre-1. Compounds 6a, 7a, 7b and 7i having substitutents at 3 position of phenyl ring are found to show higher cytokinin activity than benzyladenine at all concentrations (Table II).

Synthesis, biological activity, and molecular modeling investigation of new pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives as human A3 adenosine receptor antagonists

A new series of pyrazolotriazolopyrimidines bearing different substitutions on the phenylcarbamoyl moieties at the N5 position, being highly potent and selective human A3 adenosine receptor antagonists, is described. The compounds represent an extension and an improvement of our previous work on this class of compounds (J. Med. Chem. 1999, 42, 4473-4478; J. Med. Chem. 2000, 43, 4768-4780). All the synthesized compounds showed A3 adenosine receptor affinity in the subnanomolar range and high levels of selectivity in radioligand binding assays at the human A1, A2A, A2B, and A3 adenosine receptors. In particular, the effect of the substitution and its position on the phenyl ring have been studied. From binding data, it is evident that the unsubstituted derivatives on the phenyl ring (e.g., compound 59, hA3 = 0.16 nM, hA1/hA3 = 3713, hA2A/hA3 = 2381, hA2B/hA3 = 1388) showed the best profile in terms of affinity and selectivity at the human A3 adenosine receptors. The introduction of a sulfonic acid moiety at the para position on the phenyl ring was attempted in order to design water soluble derivatives. However, this substitution led to a dramatic decrease of affinity at all four adenosine receptor subtypes. A computer-generated model of the human A3 receptor was built and analyzed to better interpret these results, demonstrating that steric control, in particular at the para position on the phenyl ring, plays a fundamental role in the receptor interaction. Some of the synthesized compounds proved to be full antagonists in a specific functional model, where the inhibition of cAMP-generation by IB-MECA was measured in membranes of CHO cells stably transfected with the human A3 receptor with IC50 values in the nanomolar range, with a statistically significative linear relationship with the binding data.

Inhibition of serine proteases: Activity of 1,3-diazetidine-2,4-diones

The present work demonstrates that the 1,3-diazetidine-2,4-dione nucleus is effective as a scaffold of serine protease inhibitors. Compound 1 displayed high activity against human cathepsin G and α-chymotrypsin (0.39, 0.69 nM). Compound 6 exhibited 0.85 nM inhibition of human chymase. Compound 10 was a selective inhibitor against human neutrophil elastase.

Bis(alkylthio)carbenes as novel reagents for organic synthesis

Bis(alkylthio)carbenes have been shown to be a useful class of reactive intermediates for applications to organic synthesis. Substituted hydroindolones, isatins and hydroquinolones can be prepared by the addition of these carbenes to vinyl isocyanates. (C) 2000 Elsevier Science Ltd.

Synthesis of new fluorine substituted hydrazinecarboxamides and hydrazine carbothioamides having antitubercular and fungicidal activity

3-(Trifluoromethyl)phenylhydrazine 3 on condensation with substituted phenylisocyanates 2a-f and phenylisothiocyanates 2g-1 gives N,2-diphenylhydrazinecarboxamides 4a-f and N,2-diphenylhydrazine carbothioamides 4g-1 which have been found to show antitubercular and antifungal activity.

Rapid construction of isatin derivatives via addition of bis(alkylthio)carbenes to aryl isocyanates

Thermally induced cyclization between bis(alkylthio)carbenes, derived from the corresponding oxadiazolines, and substituted aryl isocyanates provides access to a variety of isatin derivatives with good efficiency.