52119-38-7

Basic information

• Product Name: ETHYL 3-(3-NITROPHENYL)-3-OXOPROPANOATE
• Synonyms: ETHYL 3-(3-NITROPHENYL)-3-OXOPROPANOATE;ETHYL 3-NITROBENZOYLACETATE;ETHYL-2-(3-NITROBENZOYL)-ACETATE;3-(3-NITRO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER;ethyl 3-(m-nitrophenyl)-3-oxopropionate;3-Nitrobenzoylacetic acid ethyl ester;3-Oxo-3-(3-nitrophenyl)propanoic acid ethyl ester;3-Oxo-3-(3-nitrophenyl)propionic acid ethyl ester
• CAS NO: 52119-38-7
• Molecular Formula: C₁₁H₁₁NO₅
• Molecular Weight: 237.21
• EINECS: 257-670-4
• Product Categories: C10 to C11;Carbonyl Compounds;Esters
• Mol File: 52119-38-7.mol

Chemical Properties

• Melting Point: 75-77 °C(lit.)
• Boiling Point: 314.37 °C at 760 mmHg
• Flash Point: 129.277 °C
• Appearance: /
• Density: 1.277 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.52±0.46(Predicted)
• CAS DataBase Reference: ETHYL 3-(3-NITROPHENYL)-3-OXOPROPANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-(3-NITROPHENYL)-3-OXOPROPANOATE(52119-38-7)
• EPA Substance Registry System: ETHYL 3-(3-NITROPHENYL)-3-OXOPROPANOATE(52119-38-7)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 52119-38-7(Hazardous Substances Data)

Usage

Uses

ETHYL 3-(3-NITROPHENYL)-3-OXOPROPANOATE is used as a chemical intermediate for the synthesis of Dithiolethiones. Dithiolethiones are a class of compounds with potential applications in various fields, including pharmaceuticals and materials science. ETHYL 3-(3-NITROPHENYL)-3-OXOPROPANOATE serves as a key building block in the preparation of these molecules, contributing to their unique properties and potential uses.
Used in Pharmaceutical Research:
ETHYL 3-(3-NITROPHENYL)-3-OXOPROPANOATE is used as a reagent for the identification of potential neuroprotective agents. Neuroprotective agents are compounds that can protect neurons from damage or degeneration, which is particularly relevant in the context of neurodegenerative diseases such as Alzheimer's, Parkinson's, and multiple sclerosis. ETHYL 3-(3-NITROPHENYL)-3-OXOPROPANOATE plays a crucial role in the development and evaluation of these agents, helping researchers to better understand their mechanisms of action and potential therapeutic applications.

InChI:InChI=1/C11H11NO5/c1-2-17-11(14)7-10(13)8-4-3-5-9(6-8)12(15)16/h3-6H,2,7H2,1H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 121-90-4 m-nitrobenzoic acid chloride 
• 618-98-4 ethyl 3-nitrobenzoate 
• 141-78-6 ethyl acetate 
• 121-92-6 3-nitrobenzoic acid 
• 61652-82-2 1-imidazolyl(3-nitrophenyl)methanone 
• 6148-64-7 ethyl potassium malonate 
• 64-17-5 ethanol 
• 623-73-4 diazoacetic acid ethyl ester 
• 99-61-6 3-nitro-benzaldehyde 
• 7772-99-8 stannous chloride 
• 1071-46-1 hydrogen ethyl malonate 
• 2414-98-4 magnesium ethylate 
• 93257-82-0 ethyl-2-(3-nitrobenzoyl)-3-oxobutanoate 

Downstream Products

• 98305-66-9 2-amino-6-(3-nitrophenyl)pyrimidin-4(3H)-one 
• 75318-44-4 4-chloro-5H-1,2,3-dithiazole-5-thione 
• 1037508-03-4 2-(3-nitrobenzoyl)-succinic acid 4-t-butyl ester 1-ethyl ester 
• 1240506-02-8 ethyl 3-(3-nitrophenyl)-3-oxo-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanoate 
• 1346441-03-9 N-(3-(1-benzyl-7-oxo-1,6,7,8-tetrahydropyrazolo[4,3-b][1,4]diazepin-5-yl)phenyl)-3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzamide 
• 1346441-06-2 N-(3-(1-benzyl-7-oxo-1,6,7,8-tetrahydropyrazolo[3,4-b][1,4]diazepin-5-yl)phenyl)-4-morpholino-3-(trifluoromethyl)benzamide 
• 1346441-10-8 1-(3-(1-benzyl-7-oxo-1,6,7,8-tetrahydropyrazolo[3,4-b][1,4]diazepin-5-yl)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea 
• 1346441-20-0 1-(3-(1-(4-methoxybenzyl)-7-oxo-1,6,7,8-tetrahydropyrazolo[3,4-b][1,4]diazepin-5-yl)phenyl)-3-(3-morpholino-5-(trifluoromethyl)phenyl)urea 
• 1346441-24-4 1-(3-chlorophenyl)-3-(3-(1-(4-methoxybenzyl)-7-oxo-1,6,7,8-tetrahydropyrazolo[3,4-b][1,4]diazepin-5-yl)phenyl)urea 
• 1346441-26-6 1-(4-chlorophenyl)-3-(3-(1-(4-methoxybenzyl)-7-oxo-1,6,7,8-tetrahydropyrazolo[3,4-b][1,4]diazepin-5-yl)phenyl)urea 
• 1346441-30-2 1-(3,5-dichlorophenyl)-3-(3-(1-(4-methoxybenzyl)-7-oxo-1,6,7,8-tetrahydropyrazolo[3,4-b][1,4]diazepin-5-yl)phenyl)urea 
• 1346441-32-4 1-(3,4-dichlorophenyl)-3-(3-(1-(4-methoxybenzyl)-7-oxo-1,6,7,8-tetrahydropyrazolo[3,4-b][1,4]diazepin-5-yl)phenyl)urea 
• 1346441-36-8 1-(3-(1-(4-methoxybenzyl)-7-oxo-1,6,7,8-tetrahydropyrazolo[3,4-b][1,4]diazepin-5-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea 
• 1346441-38-0 1-(3-(1-(4-methoxybenzyl)-7-oxo-1,6,7,8-tetrahydropyrazolo[3,4-b][1,4]diazepin-5-yl)phenyl)-3-(4-(trifluoromethyl)phenyl)urea 

Relevant articles and documents

NURR1 RECEPTOR MODULATORS

Described herein, inter alia, are Nurr1 receptor modulators and uses thereof. In an aspect is provided a method for treating a disease associated with dysregulation and/or degeneration of dopaminergic neurons in the central nervous system of a subject in need thereof, the method including administering to the subject in need thereof a therapeutically effective amount of a compound described herein.

Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters

We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

Discovery of novel 4-aryl-thieno[1,4]diazepin-2-one derivatives targeting multiple protein kinases as anticancer agents

A series of 4-aryl-thieno[1,4]diazepin-2-one were synthesized and evaluated for their antiproliferative activities against the A375P melanoma and U937 hematopoietic cell lines. Several compounds showed very potent antiproliferative activities toward both cell lines and the activities were better than that of sorafenib, the reference standard. Derivatives were made as amide (8a–8i, 9a–9m) and urea (10a–10d, 11a–11d) with diverse hydrophobic moieties. One of the most potent inhibitor 10d, 1-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(4-(2-oxo-2,3-dihydro-1H-thieno [3,4-b][1,4]diazepin-4-yl)phenyl)urea was found to be very potent inhibitor of multi-protein kinases including FMS kinase (IC50 = 3.73 nM) and is a promising candidate for further development in therapeutics for cancer.

Syntheses of phenylpyrazolodiazepin-7-ones as conformationally rigid analogs of aminopyrazole amide scaffold and their antiproliferative effects on cancer cells

Recently, we have reported the syntheses and antiproliferative activities of N-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl amide derivatives on melanoma cells. As a continuous work for antiproliferative agents in melanoma, here we report the synthesis of conformationally rigid analogs, phenyl-6,8- dihydropyrazolo[3,4-b][1,4]diazepin-7(1H)-one derivatives 7a-g, 8a-o and their antiproliferative activities against A375P melanoma cell line and U937 hematopoietic cell line. Most compounds showed competitive antiproliferative activities to sorafenib, the reference standard. Among them, N-(3-(1-benzyl-7-oxo-1,6,7,8-tetrahydropyrazolo[3,4-b][1,4]diazepin-5-yl)phenyl) -4-chloro-3-(trifluoro methyl)benzamide-amino-1-(4-methoxybenzyl)-1H-pyrazol-4- yl)-5-(3-(4-chloro-3-(trifluoromethyl) phenyl) ureido)-2-methylbenzamide (7b) exhibited potent activities (GI50 = 0.43 μM and 0.06 μM) on both cell lines. It has been further confirmed to be a potent and selective Raf kinases inhibitor and also mild inhibitor of PI3Kα.

PYRIMIDINONE DERIVATIVES OR PYRIDAZINONE DERIVATIVES FOR INHIBITION OF FACTOR VIIA ACTIVITY

The present invention relates to the pyrimidinone compound or pyridazinone compound having inhibition activity against FVIIa. Precisely, the present invention relates to a pharmaceutical composition for the prevention of blood clotting and the treatment of thrombosis containing the pyrimidinone compound or pyridazinone compound having inhibition activity against FVIIa and a prodrug, a hydrate, a solvate, an isomer and a pharmaceutically acceptable salt thereof as an active ingredient.

OXYGEN OR SULFUR CONTAINING 5-MEMBERED HETEROAROMATICS AS FACTOR Xa INHIBITORS

The present application describes oxygen and sulfur containing heteroaromatics and derivatives thereof of formula (I), or pharmaceutically acceptable salt or prodrug forms thereof, wherein J is O or S and D may be C(=NH)NH2, which are useful as inhibitors of factor Xa.

Phenyl-isoxazoles as factor XA Inhibitors

The present application describes oxygen and sulfur containing heteroaromatics and derivatives thereof of formula or pharmaceutically acceptable salt or prodrug forms thereof, wherein J is O or S and D may be C(=NH)NH2, which are useful as inhibitors of factor Xa.

Simple and high yielding syntheses of β-keto esters catalysed by zeolites

Simple and high yielding syntheses of several β-keto esters, catalysed by zeolite Hβ are reported. The methods developed include condensation of aldehydes with ethyl diazoacetate and transesterification of β-keto esters with primary, secondary, allylic and benzylic alcohols etc., all catalysed by Hβ. It was further observed that under microwave irradiation the yields of many aromatic β-keto esters were enhanced appreciably.

Tricyclic dihydropyridazinones and pharmaceutical compositions containing them

The tricyclic dihydropyridazinone derivatives having formula I STR1 are endowed with interesting hypotensive, vasodilating, antiaggregant, antithrombotic and cytoprotective properties and are therefore useful in human or veterinary medicine.