62071-76-5

Usage

Uses

Used in Organic Synthesis:
3-NAPHTHALEN-1-YL-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a building block in organic synthesis for its ability to produce a variety of other compounds. Its unique structure and reactivity make it a valuable component in the creation of complex organic molecules.
Used in Laboratory Research:
This chemical is predominantly employed in laboratory research settings, where it contributes to the advancement of scientific knowledge and the development of new chemical processes. Its use in research is driven by its potential to facilitate the discovery of novel compounds and reactions.

InChI:InChI=1/C15H14O3/c1-2-18-15(17)10-14(16)13-9-5-7-11-6-3-4-8-12(11)13/h3-9H,2,10H2,1H3

Upstream product

• 941-98-0 1'-naphthacetophenone 
• 105-58-8 Diethyl carbonate 
• 141-78-6 ethyl acetate 
• 6148-64-7 ethyl potassium malonate 
• 879-18-5 naphthalene-1-carbonic acid chloride 
• 109-94-4 formic acid ethyl ester 
• 96563-26-7 ethyl 3-hydroxy-3-naphthalen-1-ylpropanoate 
• 66-77-3 1-naphthaldehyde 
• 86-55-5 1-naphthalenecarboxylic acid 

Downstream Products

• 5472-84-4 3-hydroxy-phenalen-1-one 
• 67222-12-2 3-[1]naphthyl-3-oxo-propionic acid anilide 
• 5821-59-0 phenalene-1,3-dione 
• 62071-64-1 7-hydroxy-4-(1-naphthyl)-2H-chromen-2-one 
• 91-64-5 coumarin 
• 289709-40-6 2-(Naphthalene-1-carbonyl)-4-oxo-4-phenyl-butyric acid ethyl ester 
• 1426341-72-1 1-ethoxy-3-(naphthalen-1-yl)-1,3-dioxopropan-2-yl benzoate 

Relevant academic research and scientific papers

Trifluoroethanol as a Unique Additive for the Chemoselective Electrooxidation of Enamines to Access Unsymmetrically Substituted NH-Pyrroles

An electrochemical method for the synthesis of unsymmetrically substituted NH-pyrroles is described. The synthetic strategy comprises a challenging heterocoupling between two structurally diverse enamines via sequential chemoselective oxidation, addition,

Aromaticity-Driven Access to Cycloalkyl-Fused Naphthalenes

We report the efficient synthesis of cycloalkyl-fused naphthalenes through the [4 + 2]-cycloaddtion/decarboxylative aromatization of alkyne-tethered aryne insertion adducts. These scaffolds were difficult to synthesize using conventional reactions. The reaction proceeds via the formation of a benzopyrylium intermediate followed by intramolecular [4 + 2] cycloaddition and a subsequent decarboxylation pathway. This method is also compatible with allene-tethered substrates to afford similar products. In addition, the one-pot synthesis of polysubstituted naphthalenes via aryne insertion/benzannulation has also been developed in good yield.

An efficient route for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives promoted by CBr4 in one pot

A metal-free one-pot method for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives was proposed mediated by CBr4. The reaction went through ring formation and opening processes with only two protons leaving and the thermodynamically favorable products were selectively formed in moderate to good yields.

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF

Small molecule calpain modulator compounds, including their pharmaceutically acceptable salts, can be included in pharmaceutical compositions. The compounds can be useful in inhibiting calpain, or competitive binding with calpastatin, by contacting them with CAPN1, CAPN2, and/or CAPN9 enzymes residing inside a subject. The compounds and composition can also be administered to a subject in order to treat a fibrotic disease or a secondary disease state or condition of a fibrotic disease.

Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters

Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30 substrates were successfully converted to the desired compounds in mostly moderate to good yields.

Targeting tubulin polymerization by novel 7-aryl-pyrroloquinolinones: Synthesis, biological activity and SARs

Earlier studies had confirmed that the 7-phenylpyrroloquinolinone (7-PPyQ) nucleus was an important scaffold for new chemotherapeutic drugs targeting microtubules. For wide-ranging SARs, a series of derivatives were synthesized through a robust procedure. For comparison with the reference 3-ethyl-7-PPyQ 31, the angular geometry and substituents at the 3 and 7 positions were varied to explore interactions inside the colchicine site of tubulin. Of the new compounds synthesized, potent cytotoxicity (low and sub-nanomolar GI50 values) was observed with 21 and 24, both more potent than 31, in both leukemic and solid tumor cell lines. Neither compound 21 nor 24 induced significant cell death in normal human lymphocytes, suggesting that the compounds may be selectively active against cancer cells. In particular, 24 was a potent inducer of apoptosis in the A549 and HeLa cell lines. With both compounds, induction of apoptosis was associated with dissipation of the mitochondrial transmembrane potential and production of reactive oxygen species, indicating that cells treated with the compounds followed the intrinsic pathway of apoptosis. Moreover, immunoblot analysis revealed that compound 24 even at 50 nM reduced the expression of anti-apoptotic proteins such as Bcl-2 and Mcl-1. Finally, molecular docking studies of the newly synthesized compounds demonstrate that active pyrroloquinolinone derivatives strongly bind in the colchicine site of β-tubulin.

SMALL MOLECULE INHIBITORS OF LACTATE DEHYDROGENASE AND METHODS OF USE THEREOF

Provided is a compound of formula (I)[Formula (I) should be inserted here], in which Ar1, R1, U, V, W, X, and p are as described herein. Also provided are methods of using a compound of formula (I), including a method of treating cancer, a method of treating a patient with cancer cells resistant to an anti-cancer agent, and a method of inhibiting lactate dehydrogenase A (LDHA) and/ or lactate dehydrogenase B (LDHB) activity in a cell.

1,5-Diketones Synthesis via Three-Component Cascade Reaction

A mild and efficient cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine, 1,3-dicarbonyl compounds, and trifluoromethyl β-diketones has been developed. This cascade reaction occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl β-diketones.

2-ARYLNAPHTHYRIDIN-4-ONES AS POTENT ANTITUMOR AGENTS TARGETING TUMORIGENIC CELL LINES

In order to search for new antitumor drug candidates from 2-arylnaphthyridin-4-ones (ANs), we have designed and synthesized a series of 3 '-hydroxy or 6-hydroxy derivatives of ANs. Following the antitumor activity screening, most of these compounds were found to exhibit significant activity. Among them, 2-(3-hydroxyphenyl)-5-methyl-1,8-naphthyridin-4(1H)-one (67) was the most promising. In a preliminary action mechanism study, the treatment of Hep3B hepatoma cells with compound (67) reveals that its mechanism of action is affect on microtubule and metastasis-related proteins. Then, the corresponding phosphate prodrug (86) of compound (67) was tested against Hep3B xenograft nude mice model for antitumor activity.

Copper-mediated oxidative transformation of N-allyl enamine carboxylates toward synthesis of azaheterocycles

A method for synthesis of 3-azabicyclo[3.1.0]hex-2-enes has been developed by intramolecular cyclopropanation of readily available N-allyl enamine carboxylates. Two complementary reaction conditions, CuBr-mediated aerobic and CuBr2-catalyzed-PhIO2-mediated systems effectively induced stepwise cyclopropanation via carbocupration of alkenes. Oxidative cyclopropane ring-opening of 5-substituted 3-azabicyclo[3.1.0]hex-2-enes was also developed for synthesis of highly substituted pyridines. In addition, diastereoselective reduction of 3-azabicyclo[3.1.0]hex-2-enes to 3-azabicyclo[3.1.0]hexanes was achieved using NaBH3CN in the presence of acetic acid.