256378-54-8

Basic information

• Product Name: 2-amino-4-(4-hydroxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile
• Synonyms: 2-amino-4-(4-hydroxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile
• CAS NO: 256378-54-8
• Molecular Formula: C19H12N2O4
• Molecular Weight: 332.30958
• Mol File: 256378-54-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-amino-4-(4-hydroxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-4-(4-hydroxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile(256378-54-8)
• EPA Substance Registry System: 2-amino-4-(4-hydroxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile(256378-54-8)

Safety Data

• Hazardous Substances Data: 256378-54-8(Hazardous Substances Data)

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 3785-90-8 2-(4-hydroxyphenylmethylene)malononitrile 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 109-77-3 malononitrile 
• 123-08-0 4-hydroxy-benzaldehyde 
• 22105-09-5 4‐hydroxycoumarin 

Relevant articles and documents

Small molecule inhibitors of white spot syndrome virus: Promise in shrimp seedling culture

Rapid production of prawn (Litopenaeus vannamei) under artificial pressure can result in a series of obvious challenges and is vulnerable to serious losses related to aquatic environmental issues and the unrestrained outbreak of white spot syndrome (WSS). However, to date, there are no therapeutic strategies to contain the spread of the virus. Here, we synthesized 27 coumarin derivatives and evaluated their anti‐white spot syndrome virus (WSSV) activity in L. vannamei larvae. We demonstrated that electron‐withdrawing and electron‐giving substituent groups play an im-portant role in reducing toxicity and WSSV replication, respectively. Two coumarin C2 (2‐amino‐5‐ oxo‐4‐(p‐tolyl)‐4H,5H‐pyrano[3,2‐c]chromene‐3‐carbonitrile) and C7 (2‐amino‐4‐(4‐chlorophenyl)‐ 5‐oxo‐4H,5H‐pyrano[3,2‐c]chromene‐3‐carbonitrile) were regarded as the most promising anti‐ WSSV compounds with maximum antiviral response 5% and median effective concentration 10 mg/L. The mortality of WSSV‐infected larvae decreased by more than 60% after exposure to C2 and C7. With continuous immersion of C2 and C7 exchange, the mortality further decreased to 40% at 120 h.Additionally, C2 and C7 are the relatively stable in aquacultural water, making these agents suitable for use in inhibiting WSSV horizontal transmission in static aquaculture systems. These results showed the marked advantages of using C2 and C7 in the shrimp industry, and suggest that they hold potential for the treatment and prevention of WSSV infection in shrimp seedling culture.

Rational design, synthesis and SAR study of novel warfarin analogous of 4-hydroxy coumarin-beta-aryl propanoic acid derivatives as potent anti-inflammatory agents

Synthesis of highly potent and enhanced safety profiled antiinflammatory drugs has become a challenging task in the drug discovery process. A library of warfarin analogue 3-(4?hydroxy-2-oxo-2H-chromen-3-yl)-3-arylpropanoic acid derivatives have been synthesised and their structures were established by availing different analysis techniques. The invitro COX-1/COX-2 study revealed the effective potency of the selective compounds 2b(IC50=180.45 μl/ml), 2c(IC50=21.03 μl/ml) and 2f(IC50=120.45 μl/ml) against COX-2 compared to reference drug aspirin (IC50=121.60 μl/ml). Compound 2c is more selective towards COX-2 with a high selective index of 7.42 than standard aspirin with a selective index of 4.14. Further, the target molecules were assessed for their antiinflammatory activity against MMP2 and MMP9, the results revealing a high percentage of inhibition. While, protein denaturation study displayed high potency of the compounds 2a (IC50=13.32 μg/ml), 2 g (IC50=11.14 μg/ml) and 2l (IC50=4.71 μg/ml) as compared with aspirin (IC50=13.42 μl/ml). The docking studies were established to understand the structural features responsible for biological activity and the outcome of the docking studies are indeed following the experimental results.

Green synthesis of dihydropyrano[3,2-c]chromene derivatives using amino-terminated PAMAM dendrimer as catalyst

d-Sorbitol-cored PAMAM dendrimer (SOR-G1) was effectively synthesized by the ring opening polymerization of epichlorohydrin. The dendrimer was characterized using different spectroscopic and analytical techniques including IR and NMR spectroscopy, TG–DTA,

A new approach for the synthesis of biologically active chromene compounds using a photo catalyst TiO2-Ag

A green and efficient method for the synthesis of chromene derivatives using TiO2 doped Ag as a photocatalyst under visible light irradiation at room temperature is reported. The advantages of our method are clean reaction condition, easy workup procedure, use of eco-friendly solvent, and recyclable catalyst and most importantly higher yield of the product. The photocatalyst was found to be highly efficient for the synthesis of chromene derivatives within a short reaction time. The photocatalyst was prepared and characterized by Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), scanning electron microscope (SEM), energy dispersive X-ray spectroscopy (EDS), and powder XRD technique and thermogravimetric analysis (TGA). In addition, the in-vitro study of helminths against S. obvelata were investigated and it was found that chromene derivatives were active against S. obvelata and showed no sign of acute toxicity in mice.

Zr@IL-Fe3O4MNPs as an efficient and green heterogeneous magnetic nanocatalyst for the one-pot three-component synthesis of highly substituted pyran derivatives under solvent-free conditions

The present study was conducted to synthesize Zr@IL-Fe3O4MNPs as a new magnetically recoverable heterogeneous catalyst, which was then characterized by Fourier transform infrared (FT-IR) spectroscopy, energy dispersive X-ray spectros

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The novel organic–inorganic nanohybrid magnetic nanoparticles (HNPs@Py) were prepared by a simple method and characterized by FT-IR, XRD, FE-SEM, TGA, VSM, EDX, and MAP. The catalytic activity of this new (HNPs@Py) was studied for green synthesis of bisco

Synthesis of Fe3O4-supported Schiff base Cu (II) complex: a novel efficient and recyclable magnetic nanocatalyst for one-pot three-component synthesis of quinolin-5-one, chromene-3-carbonitrile and phthalazine-5,10-dione derivatives

In this research, synthesis and characterization of a novel Schiff base Cu (II) complex immobilized on Fe3O4@SiO2 nanoparticles are reported. Then, the catalytic activity of these nanoparticles as magnetic recyclable nanocatalyst was explored for the one-pot three-component synthesis of quinolin-5-one, chromene-3-carbonitrile and phthalazine-5,10-dione derivatives. The reactions proceeded smoothly to provide the respective products in excellent yields under green conditions. Facile preparation of the catalyst, high yields of the products, low reaction times, and use of water as green solvent are the main advantages of the present protocol. Moreover, the catalyst can be easily separated from the reaction mixture in a magnetic field, recycled and reused for six consecutive fresh runs without considerable loss of catalytic activity. Graphic abstract: [Figure not available: see fulltext.]

One‐pot and green synthesis 1H-pyrazolo[1,2-b]phthalazine-5,10-dione and dihydropyrano[3,2-c]chromene derivatives by Fe3O4@SiO2-imine/phenoxy-Cu(II) as an efficient and reusable catalyst

In the current study, magnetite-silica core–shell nanoparticles modified with Cu-salen complex (Fe3O4@SiO2-imine/phenoxy-Cu(II)) was utilized as a heterogeneous catalyst for the one-pot multicomponent synthesis of 1H-pyraz

A synergetic role of Aegle marmelos fruit ash in the synthesis of biscoumarins and 2-amino-4H-chromenes

Abstract: A dry rind of Aegle marmelos (bael) fruit ash as a synergetic alternative material to an expensive, toxic and corrosive catalysts for the synthesis of biscoumarins and 2-amino-4H-chromenes at ambient temperature in water is reported. The spectro

Silica chemisorbed bis(hydrogensulphato)benzene (SiO2-BHSB) as a new, efficient, and recyclable catalyst for the synthesis of 5-oxopyrono[3,2-c]chromene scaffolds in water-based solvent

The synthesis of silica chemisorbed bis(hydrogensulphato)benzene (SiO2-BHSB) as a new hybrid material was achieved by a sequence of three reactions. Structural features of the synthesized SiO2-BHSB were established by using analytica