112434-52-3

Basic information

• Product Name: 2H-Pyrano[2,3-d]pyrimidine-6-carbonitrile, 7-amino-1,3,4,5-tetrahydro-5-(4-methoxyphenyl)-2,4-dioxo-
• CAS NO: 112434-52-3
• Molecular Formula: C15H12N4O4
• Molecular Weight: 312.285
• Mol File: 112434-52-3.mol
• Article Data: 48

Chemical Properties

• CAS DataBase Reference: 2H-Pyrano[2,3-d]pyrimidine-6-carbonitrile, 7-amino-1,3,4,5-tetrahydro-5-(4-methoxyphenyl)-2,4-dioxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyrano[2,3-d]pyrimidine-6-carbonitrile, 7-amino-1,3,4,5-tetrahydro-5-(4-methoxyphenyl)-2,4-dioxo-(112434-52-3)
• EPA Substance Registry System: 2H-Pyrano[2,3-d]pyrimidine-6-carbonitrile, 7-amino-1,3,4,5-tetrahydro-5-(4-methoxyphenyl)-2,4-dioxo-(112434-52-3)

Safety Data

• Hazardous Substances Data: 112434-52-3(Hazardous Substances Data)

Upstream product

• 67-52-7 BARBITURIC ACID 
• 2826-26-8 2-(4-methoxyphenylmethylene)malononitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 109-77-3 malononitrile 
• 67-52-7 6-hydroxyuracil 
• 67-52-7 pyrimidine-2,4,6-triol 

Relevant articles and documents

β-CD-catalyzed multicomponent domino reaction: synthesis, characterization, in silico molecular docking and biological evaluation of pyrano[2,3-d]-pyrimidinone derivatives

Abstract: Simple and green synthetic procedures constitute an important goal in organic synthesis. The combination of multicomponent reactions (MCRs) and unconventional solvents has become a new research direction, which enables simultaneous growth of bot

Magnetic nanoporous MCM-41 supported ionic liquid/palladium complex: An efficient nanocatalyst with high recoverability

In this study, a novel magnetic mesoporous MCM-41 silica supported ionic liquid/palladium complex (Fe3O4@MCM@IL/Pd) with core-structure was prepared and characterized and its catalytic performance was developed under green conditions

Synthesis, biological activity and POM/DFT/docking analyses of annulated pyrano[2,3-d]pyrimidine derivatives: Identification of antibacterial and antitumor pharmacophore sites

New annulated pyrano[2,3-d]pyrimidine derivatives were synthesized with hydroxyl, methoxy, bromine, nitrile and nitro substituents on its skeleton. The correlated electronic effect of substituents on the magnitude of antibacterial activity was noted. The

Design, synthesis, molecular docking and in silico ADMET profile of pyrano[2,3-d]pyrimidine derivatives as antimicrobial and anticancer agents

Pyrano[2,3-d]pyrimidine derivatives were synthesized by treating cyclic compounds containing active methylene group with aldehyde and malononitrile in butanol. The behavior of pyrano[2,3-d]pyrimidine towards some electrophlies namely triethylorthoformate followed by nitrogen nucleophiles as isobutylamine, urea, phenylthiourea, p-toluidine, o-phenylenediamine, o-aminophenol, 2-amino-4-methyl-pyridine and acetic acid with the aim of obtaining some interesting non-mixed heterocyclic compounds. All synthesized compounds to some extent have shown good antimicrobial activity against different microbial strains that had been extracted by inhibiting cell wall synthesis. Compound 5b showed the highest antibacterial activities against B. subtilis, S. aureus and E. coli. On the other hand compound 5 g exhibited the highest antibacterial and antifungal activities against P. aeruginosa and A. niger respectively. In addition, they explore cytotoxic potentialities against different cell lines via DNA intercalation and Top-II inhibition. The cytotoxic activities clarify the strong inhibitory activity of derivative 5a against HepG2 cells with IC50 = 2.09 μM, while HCT-116 cells were highly susceptible to derivative 5c with IC50 = 2.61 μM, in the meantime, derivative 5f showed pronounced negative impact against MCF-7 (IC50 = 2.43 μM) when compared with other prepared compounds. All derivatives exhibited higher anticancer activities than doxorubicin against the three cell lines except compound 2 against both HepG2 and MCF-7 and compound 5e against HepG2 cell lines. Compounds 5a, 5c and 5f potently intercalate DNA at IC50 values of 26.96, 27.13 and 29.86 μM respectively, which were more potent than doxorubicin (IC50 value of 31.27 μM). Moreover, compounds 5a, 5c and 5f exhibited very good Topoisomerase II inhibitory activities with IC50 values of 0.752, 0.791 and 0.776 μM respectively, that were more potent than that of doxorubicin (IC50 = 0.94 μM). For a great extent, the molecular modeling studies were in agreement with that of in vitro cytotoxicity activity, DNA binding and Top-II inhibition results.

Water Mediated Domino Knoevenagel-Michael-cyclocondensation Reaction of Malononitrile, Various Aldehydes and Barbituric Acid Derivatives Using Boric Acid Aqueous Solution System Compared with Nano-titania Sulfuric Acid

Nano-titania sulfuric acid (TSA) and boric acid [B(OH)3] were efficiently utilized for domino Knoevenagel-Michael-cyclocondensation reaction of malononitrile, various aldehydes and barbituric acid derivatives to synthesis of pyrano[2,3-d]pyrimi

Three-component synthesis of pyrano[2,3-d]pyrimidinone derivatives catalyzed by Ni2+ supported on hydroxyapatite-core–shell-γ-Fe2O3 nanoparticles in aqueous medium

Pyrano[2,3-d]pyrimidine derivatives were synthesized via one-pot, three-component condensation reaction of aromatic aldehydes, malononitrile, and barbituric acid in aqueous ethanol catalyzed by Ni2+ supported on hydroxyapatite-core–shell-γ-Fes

The introduction of two new imidazole-based bis-dicationic Br?nsted acidic ionic liquids and comparison of their catalytic activity in the synthesis of barbituric acid derivatives

In this article, the preparation of bis-imidazolium hydrogen sulfate and bis-imidazolium perchlorate as two new bis-dicationic Br?nsted acidic ionic liquids based on imidazole is reported. After characterization by FT-IR, mass and NMR spectroscopy and pH titration, the applicability of these reagents is studied in the promotion of the synthesis of 5-arylidene barbituric acids and pyrano[2,3-d] pyrimidinone derivatives. These methods possess some advantages such as ease of preparation of the catalyst, simple work-up procedure, short reaction times, excellent yields, and use of nonorganic solvents during all steps of the reactions and good reusability of the catalysts.

WELPSA: A natural catalyst of alkali and alkaline earth metals for the facile synthesis of tetrahydrobenzo[b]pyrans and pyrano[2,3-d]pyrimidinones as inhibitors of SARS-CoV-2

Since 2019, the infection of SARS-CoV-2 has been spreading worldwide and caused potentially lethal health problems. In view of this, the present study explores the most commodious and environmentally benign synthetic protocol for the synthesis of tetrahyd

Efficient biogenesis of Cu2O nanoparticles using extract of Camellia sinensis leaf: Evaluation of catalytic, cytotoxicity, antioxidant, and anti-human ovarian cancer properties

At the moment, metallic nanoparticles especially copper nanoparticles are administrated for the cure of different disorders, such as tumor and cancer. In recent years, many chemotherapeutic supplements have been formulated by copper nanoparticles. In the