487034-01-5

Usage

Uses

Used in Medicinal Chemistry:
3-(4-NITRO-PHENYL)-ISOXAZOLE-5-CARBOXYLIC ACID METHYL ESTER is used as a building block for the synthesis of various pharmaceuticals and agrochemicals. It serves as a key component in the development of new drugs and pesticides.
Used in Research:
3-(4-NITRO-PHENYL)-ISOXAZOLE-5-CARBOXYLIC ACID METHYL ESTER is used as a tool compound in research for studying the pharmacological and biochemical properties of isoxazole derivatives. It aids in understanding the mechanisms of action and potential therapeutic applications of these compounds.
Used in Antimicrobial Development:
3-(4-NITRO-PHENYL)-ISOXAZOLE-5-CARBOXYLIC ACID METHYL ESTER has been found to exhibit antibacterial and antifungal properties, making it a potential candidate for the development of new antimicrobial agents. Its activity against various pathogens highlights its potential in addressing the growing need for effective treatments against drug-resistant infections.

Upstream product

• 100-19-6 (4-nitrophenyl)ethanone 
• 39757-36-3 4-(4-Nitro-phenyl)-2,4-dioxo-butyric acid methyl ester 
• 553-90-2 Dimethyl oxalate 

Downstream Products

• 1062547-90-3 C₁₀H₇N₃O₅ 
• 33282-25-6 5-(4-nitrophenyl)-isoxazole-3-carboxylic acid 
• 879217-72-8 5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid 
• 879216-20-3 5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester 
• 879216-19-0 5-[4-(5,5-dimethyl-4-oxo-hexanoylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester 
• 879216-18-9 5-(4-amino-phenyl)-isoxazole-3-carboxylic acid methyl ester 

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.

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.

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.

Rapid assembly and in situ screening of bidentate inhibitors of protein tyrosine phosphatases

We have successfully designed and synthesized a small library of protein tyrosine phosphatase (PTP) inhibitors, in which the so-called "click chemistry" or Cu(I)-catalyzed 1,3-dipolar alkyne-azide coupling reaction was carried out for rapid assembly of 66 different bidentate compounds. Subsequent in situ enzymatic screening revealed a potential PTP1B inhibitor (IC50 = 4.7 μM) which is 10-100 fold more potent than other PTPs.