3034-09-1

Basic information

• Product Name: 2-(4-Nitrophenyl)-2,3-dihydro-4H-1-benzopyran-4-one
• Synonyms: 2-(4-Nitrophenyl)-2,3-dihydro-4H-1-benzopyran-4-one;2-(4-Nitrophenyl)chroman-4-one;4'-Nitroflavanone
• CAS NO: 3034-09-1
• Molecular Formula: C₁₅H₁₁NO₄
• Molecular Weight: 269.25
• Mol File: 3034-09-1.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-Nitrophenyl)-2,3-dihydro-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Nitrophenyl)-2,3-dihydro-4H-1-benzopyran-4-one(3034-09-1)
• EPA Substance Registry System: 2-(4-Nitrophenyl)-2,3-dihydro-4H-1-benzopyran-4-one(3034-09-1)

Safety Data

• Hazardous Substances Data: 3034-09-1(Hazardous Substances Data)

Usage

Class

Benzopyran compounds

Contains

Nitrophenyl group

Usage

Pharmaceutical research

Potential activities

Anti-inflammatory, antioxidant, anticancer

Potential as

Fluorescent probe for sensing metal ions

Ongoing research

Exploring potential applications in various fields.

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 118-93-4 o-hydroxyacetophenone 
• 491-38-3 1-benzopyran-4(4H)-one 
• 24067-17-2 4-nitrophenylboronic acid 
• 161226-49-9 4'-nitro-2-hydroxychalcone 
• 38270-09-6 1-(2-hydroxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one 
• 1469-94-9 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione 
• 38270-09-6 (E)-2'-hydroxy-4-nitrochalcone 

Downstream Products

• 107916-52-9 2-(4-nitro-phenyl)-chroman-3,4-dione-3-oxime 
• 38270-09-6 (E)-2'-hydroxy-4-nitrochalcone 
• 19725-49-6 4'-nitroflavone 
• 120185-88-8 3-(4-nitrophenyl)-4H-1-benzopyran-4-one 
• 534569-39-6 C₁₆H₁₄N₄O₄ 
• 108896-95-3 3-acetoxy-2-(4-nitro-phenyl)-chromen-4-one 
• 77038-21-2 4'-nitro-3-methylene flavanone 

Relevant articles and documents

Guanidino-graphene catalysed synthesis of flavones via Aldol-Michael-oxidation

Guanidino-graphene has been synthesized by the reaction of bromoamine with reduced graphene oxide and characterized by FT-IR, Raman, TGA, powder XRD, TEM, SEM, and zeta potential. It is a cheap, heterogeneous and environmentally benign solid base catalyst used for cascade Aldol-Michael-oxidation in the synthesis of chalcone, flavonoids.

SAR studies of o-hydroxychalcones and their cyclized analogs and study them as novel inhibitors of cathepsin B and cathepsin H

Cathepsins have emerged as a potential target for anti-cancer drug development. In the present study, we have synthesized three structurally related series of flavanoids i.e., 2′-hydroxychalcones, flavanones and flavones and assayed in vitro to study their inhibitory potency against cathepsin B and H, promising drug candidate for cancer therapy. Enzyme kinetics studies were carried out in presence of these compounds after preliminary proteolytic studies on endogenous protein substrates. SAR studies suggested that open chain flavanoids were better inhibitors as compared to their cyclized analogs. The most potent inhibitors among the three series were nitro substituted compounds 1g, 2g and 3g with Ki values of ～6.18 × 10-8 M, 4.8 × 10-7 M and 7.85 × 10-7 M for cathepsin B and Ki values of ～2.8 × 10-7 M, 31.8 × 10-6 M and 33.7 × 10 -6 M for cathepsin H, respectively. The relationship between chalcone, flavanones and flavone structures interpreted by docking studies on cathepsin B and H also provided useful insights.

Applications of caged-designed proton sponges in base-catalyzed transformations Dedicated to Professor Milan Kratochvíl for his 90th birthday anniversary.

Superbasic properties of caged proton sponges (PSs) - substituted diazatetracyclo[4.4.0.13,10.15,8]dodecanes (DTDs) - were utilized in Knoevenagel and Claisen-Schmidt condensations, the Pudovik reaction, and Michael addition. This investigation covers the influence of the solvent, reaction temperature, catalyst loadings as well as the electronic properties of substituents upon the reaction. Moreover, we provided an activity comparison between our new base and a well-known and commercially available proton sponge (DMAN). The basicity (in MeCN) of our chosen DTD (pKBH+=21.7±0.1) exceeded the prototypal PS - 1,8-bis(dimethylamino)naphthalene (DMAN, pKBH+=18.6), by three orders of magnitude. We proved that DTDs are reasonably active species in monitored reactions, which is a consequence of a hydrogen bridge angle (～130°) between the two nitrogen atoms and the captured proton. We present here syntheses of aminoindolizine, substituted 4H-chromene, and flavanones, and the unexpected formation of a bis-addition product formed after Michael addition, all under mild conditions.