39757-36-3

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-(4-NITROPHENYL)-2,4-DIOXOBUTANOATE is used as a chemical intermediate for the synthesis of pharmaceuticals. It plays a crucial role in the production of various medications, contributing to the development of new drugs and improving existing ones.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL 4-(4-NITROPHENYL)-2,4-DIOXOBUTANOATE is also utilized as an intermediate. Its involvement in the synthesis process aids in creating agrochemicals that are essential for enhancing crop protection and yield.
Used in Dye and Pigment Production:
METHYL 4-(4-NITROPHENYL)-2,4-DIOXOBUTANOATE is used as a component in the production of dyes and pigments. Its chemical properties make it suitable for creating a range of colorants used in different industries, including textiles, plastics, and printing inks.
Safety Precautions:

InChI:InChI=1/C11H9NO6/c1-18-11(15)10(14)6-9(13)7-2-4-8(5-3-7)12(16)17/h2-5H,6H2,1H3

Upstream product

• 553-90-2 Dimethyl oxalate 
• 100-19-6 (4-nitrophenyl)ethanone 

Downstream Products

• 487034-01-5 5-(4-nitro-phenyl)-isoxazole-3-carboxylic acid methyl ester 
• 889993-38-8 C₁₁H₉N₃O₄ 
• 78051-40-8 1-Benzoyl-5-hydroxy-5-(4-nitro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester 
• 1415963-70-0 methyl 7,7-dimethyl-2-(p-nitrophenyl)-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylate 
• 1416981-62-8 C₄₁H₃₃N₅O₁₀ 
• 1416981-54-8 C₃₂H₂₈N₄O₁₀ 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship of new chalcone linked 5-phenyl-3-isoxazolecarboxylic acid methyl esters potentially active against drug resistant Mycobacterium tuberculosis

In search of novel therapeutic agents active against emerging drug-resistant Mycobacterium tuberculosis and to counter the long treatment protocol of existing drugs, herein we present synthesis and biological evaluation of a new series of 5-phenyl-3-isoxazolecarboxylic acid methyl ester-chalcone hybrids. Among 35 synthesized compounds, 32 analogues displayed potent in-vitro activity against Mycobacterium tuberculosis H37Rv with MIC 0.12–16 μg/mL. Cell viability test against Vero cells indicated 29 compounds to be non-cytotoxic (CC50 > 20 μg/mL & SI > 10). Most potent compounds with MIC 0.12 μg/mL (7 b, 7j, 7 ab) exhibited selectivity index (SI) in excess of 320. Further studies on activity against drug-resistant Mycobacterium tuberculosis revealed 7j as the most potent compound with MIC 0.03–0.5 μg/mL. Time-kill kinetic study suggested compound 7j displaying concentration-dependent bactericidal killing activity with relatively comparable potency to that of current first-line anti-TB drugs. Taken together, 7j presents a novel hit with potential to be translated into a potent antimycobacterial.

Novel pyrazole derivatives having protein kinase activity and use thereof

The present invention relates to a novel pyrazole derivative compound. The present invention relates to an isomer or a pharmaceutically acceptable salt thereof and a pharmaceutical composition comprising the same. A pyrazole derivative compound is provided to selectively inhibit JNK, in particular JNK3, to be used as a pharmaceutical composition for preventing and treating neurological diseases.

Discovery of 3-alkyl-5-aryl-1-pyrimidyl-1H-pyrazole derivatives as a novel selective inhibitor scaffold of JNK3

3-alkyl-5-aryl-1-pyrimidyl-1H-pyrazole derivatives were designed and synthesised as selective inhibitors of JNK3, a target for the treatment of neurodegenerative diseases. Following previous studies, we have designed JNK3 inhibitors to reduce the molecular weight and successfully identified a lead compound that exhibits equipotent activity towards JNK3. Kinase profiling results also showed high selectivity for JNK3 among 38 kinases. Among the derivatives, the IC50 value of 8a, (R)-2-(1-(2-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)amino)pyrimidin-4-yl)-5-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)acetonitrile exhibited 227 nM, showing the highest inhibitory activity against JNK3.

Synthesis and anticancer activity of heteroaromatic linked 4β-amido podophyllotoxins as apoptotic inducing agents

A series of different heteroaromatic linked 4β-amidopodophyllotoxin conjugates (16a-i, 17a-i and 18a-d) were synthesized and evaluated for anticancer activity against five human cancer cell lines. Among the series, one of the compound 17g showed significant antiproliferative activity in A549 (lung cancer) cell line. Flow cytometric analysis showed that 17g arrested the cell cycle in the G2/M phase leading to caspase-3 dependent apoptotic cell death. Further, Hoechst 33258 staining and DNA fragmentation assay also suggests that 17g induces cell death by apoptosis.

Anthranilamide-Pyrazolo[1,5-a]pyrimidine Conjugates as p53 Activators in Cervical Cancer Cells

A library of new anthranilamide-pyrazolo[1,5-a]pyrimidine conjugates were designed, synthesized, and evaluated for their anticancer activity in cervical cancer cells such as HeLa and SiHa that possess low levels of p53. All 24 conjugates showed antiproliferative activity, while some of them exhibit significant cytotoxicity. In assays related to cell-cycle distribution, these conjugates induced G2/M arrest in HeLa cells and G1 cell-cycle arrest in SiHa cells. Immunocytochemistry assays revealed that these compounds cause nuclear translocation of p53, thereby indicating the activation of p53. In cervical cancer cells, the p53 protein is degraded by E6 oncoprotein. Immunoblot and RT-PCR analyses proved the presence of mitochondria-mediated apoptosis with involvement p53 target genes such as BAX, Bcl2, and p21 (CDKI). Moreover, these compounds increased the phosphorylated forms of p53 and provide signals for apoptosis induction. Interestingly, one of the conjugates, (2-phenyl-7-(3,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl)(4-(2-(thiophen-2-ylmethylamino)benzoyl)piperazin-1-yl)methanone, is the most promising candidate in this series and has the potential to be taken up for further detailed studies.

Efficient synthesis and utilization of phenyl-substituted heteroaromatic carboxylic acids as aryl diketo acid isosteres in the design of novel HIV-1 integrase inhibitors

Three new types of aryl diketo acid (ADK) isosteres were designed by conversion of the biologically labile 1,3-diketo unit into heteroaromatic motif such as isoxazole, isothiazole, or 1H-pyrazole to improve the physicochemical property of ADK-based HIV-1 integrase (IN) inhibitors. The synthesis of the heteroaromatic carboxylic acids was established by employing phenyl β-diketoester or benzaldehyde as the starting material and 1,3-dipolar cycloaddition as the key reaction. Of the compounds tested, the 3-benzyloxyphenyl-substituted isoxazole carboxylic acid displayed the best IN inhibitory and antiviral activities, with N-hydroxylamidation enhancing the in vitro and in vivo potency. These findings are important for further optimization of ADK-based IN inhibitors.