7338-51-4

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 2953, 1984 DOI: 10.1016/S0040-4039(01)81335-6

InChI:InChI=1/C12H10O5/c1-6-3-9(15)11-10(17-6)4-8(14)7(5-13)12(11)16-2/h3-5,14H,1-2H3

Upstream product

• 7664-93-9 sulfuric acid 
• 82-57-5 visnagin 

Downstream Products

• 106940-66-3 7-hydroxy-5-methoxy-2-methyl-6-(phenylimino-methyl)-chromen-4-one 
• 84817-15-2 4-<(7'-hydroxy-5'-methoxy-2'-methyl-4H-oxo-<1>benzopyran-6'-yl)methylene>-2-phenyloxazolin-5-one 
• 112434-57-8 2-imino-5-methoxy-8-methyl-6-oxo-3-thiocarboxamide-2H,6H-benzo<1,2-b:5,4-b'>dipyran 
• 135763-12-1 (Triphenyl-λ⁵-phosphanylidene)-acetic acid 6-formyl-5-methoxy-2-methyl-4-oxo-4H-chromen-7-yl ester 
• 106038-24-8 5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2-b:5,4-b'>dipyran 
• 791-28-6 Triphenylphosphine oxide 
• 135763-09-6 5-methoxy-8-methyl-2-thio-6-oxo-2H,6H-benzo<1,2-b:5,4-b'>dipyran 
• 84735-06-8 5-(7-hydroxy-5-methoxy-2-methyl-4-oxo-4H-1-benzopyran-6-yl)-13-methoxy-10-methyl-2-phenyl-12-oxo-12H-7,9-dioxa-3,4,6-triazabenzonaphthacene 
• 112434-58-9 3-benzoyl-2-imino-5-methoxy-8-methyl-2H,6H-pyrano[3,2-g]chromen-6-one 
• 106751-95-5 6-[(E)-Cyclohexyliminomethyl]-7-hydroxy-5-methoxy-2-methyl-chromen-4-one 
• 59955-01-0 C₉OH₂(O)(CH₃)(OCH₃)(OH)CHNC₆H₄CH₃ 
• 108843-96-5 7-hydroxy-5-methoxy-2-methyl-6-<3-phenyl-3-oxoprop-1-en-1-yl>benzopyran-4(H)-one 
• 1100363-95-8 C₂₀H₁₄FNO₄ 
• 1100363-98-1 C₂₀H₁₃Cl₂NO₄ 

Relevant academic research and scientific papers

Spectroscopic and biological activities studies of bivalent transition metal complexes of Schiff bases derived from condensation of 1,4-phenylenediamine and benzopyrone derivatives

Many tools of analysis such as elemental analyses, infrared, ultraviolet-visible, electron spin resonance (ESR) and thermal analysis, as well as conductivity and magnetic susceptibility measurements were used to elucidate the structures of the newly prepared Co(II), Ni(II) and Cu(II) complexes with Schiff bases derived from the condensation of 1,4-phenylenediamine with 6-formyl-7-hydroxy-5-methoxy-2-methylbenzo-pyran-4-one (H2L) or 5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one (H4L). The data showed that all formed complexes are 1:1 or 2:2 (M:L) and non-electrolyte chelates. The Co(II) and Cu(II) complexes of the two Schiff bases were screened for antibacterial activities by the disk diffusion method. The antibacterial activity was screened using Escherichia coli and Staphylococcus capitis but the antifungal activity was examined by using Aspergillus flavus and Candida albicans. The Results showed that the tested complexes have antibacterial, except CuH4L, but not antifungal activities.

Microplate assay for screening the antibacterial activity of Schiff bases derived from substituted benzopyran-4-one

Schiff bases (SB1-SB3) were synthesized from the condensation of 6-formyl-7-hydroxy-5-methoxy-2-methylbenzopyran-4-one with 2-aminopyridine (SB1), p-phenylenediamine (SB2) and o-phenylenediamine (SB3), while Schiff bases (SB4-SB 6) were synthesized by condensation of 5,7-dihydroxy-6-formyl-2- methylbenzopyran-4-one with 2-aminopyridine (SB4), p-phenylenediamine (SB5) and o-phenylenediamine (SB6). Schiff bases were characterized using elemental analysis, IR, UV-Vis, 1H NMR, 13C NMR and mass spectroscopy. These compounds were screened for antibacterial activities by micro-plate assay technique. Escherichia coli and Staphylococcus capitis were exposed to different concentrations of the Schiff bases. Results showed that the antibacterial effect of these Schiff bases on Gram-negative bacteria were higher than that on Gram-positive bacteria moreover, the Schiff bases containing substituent OCH3 on position five have higher antibacterial activity than that containing hydroxy group on the same position.

Convenient synthesis of linear 2H,6H-pyrano[3,2-g] chromenes from natural occurring compound; visnagin

A simple and convenient rout for the synthesis of linear 2-imino-2H,6H-pyrano[3,2-g] chromene-6-ones and 2H,6H-pyrano[3,2-g]chromene-2,6-diones has been described starting from natural occurring furochromone; visnagin (1). Ring opening of 1 yielded 6-form

Synthesis and anti-inflammatory activity of some benzofuran and benzopyran-4-one derivatives

New series of furosalicylic acids 3a - c, furosalicylanilides 6a - n, furobenzoxazines 8a - f, 1-benzofuran- 3-arylprop-2-en-1-ones 12a,b, 6-(aryl-3-oxoprop-1-enyl)-4H-chromen-4-ones 16a - c and 6-[6-aryl-2-thioxo- 2,5-dihydropyrimidin-4-yl]-4H-chromen-4-ones 17a - c were synthesized. Anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema model in rats and prostaglandin E2 (PGE2) synthesis inhibition activity. Some of the tested compounds revealed comparable activity with less ulcerogenic effect than Diclofenac at a dose 100 mg/kg. All the synthesized compounds were docked on the active site of cyclooxygenase-2 (COX-2) enzyme and most of them showed good interactions with the amino acids of the active site comparable to the interactions exhibited by Diclofenac.

Chemistry of phosphorus ylides. Part 34 : Synthesis of chromenone phosphanylidene and cyclobutylidene derivatives

The reaction of nucleophilic phosphacumulene ylides with visnaginone and khellinone afforded the corresponding phosphanylidene and furochromene derivatives. Moreover, pyranochromenes were obtained from the reaction of chromene carbaldehydes with phosphacumulenes. On the other hand, the phosphanylidene-cyclobutylidenes and their dimers were produced from the reaction of furochromene carbaldehydes with the same phosphonium reagents.

Synthesis and anticonvulsant activity of 4-oxo and 4-thioxo-8- bromobenzopyran derivatives

Several thiosemicarbazones (7 and 8), 1,3-thiazolidin-4-ones (9, 10, 13, 14) and 2-thioxo-1,3-imidazolidin-4-ones (11) have been prepared starting from 8-bromo-7-hydroxy-5-methoxy-2-methyl-4-oxo-4H-1-benzopyran-6-carbaldehyde (3) and its 4-thio analogue (4). The anticonvulsant activity of all of the synthesized compounds was evaluated against maximal electrical shock (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizures. The neurotoxicity was assessed using the rota-rod test. Some of the tested compounds displayed potent anticonvulsant activity in the scPTZ test. ECV Editio Cantor Verlag.

4-Phenoxybutoxy-substituted heterocycles - A structure-activity relationship study of blockers of the lymphocyte potassium channel Kv1.3

The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC50 of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC50s of 150 nM to 10 μM in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC50 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers.

Synthesis and anticoagulant, antipyretic and analgesic activities of some 4H-1-benzopyran-4-one derivatives

New derivatives of 7-hydroxy-5,8-dimethoxy-2-methyl-4(H)-oxo-1-benzopyran-6-carboxaldehyde (2a) have been synthesized and tested for their anticoagulant, antipyretic and analgesic activities.Compounds 2a, b and 3a, c, d show significant anticoagulant effe

Photodegradation of Natural Substances: Photooxygenation and Ozonolysis of 4-Methoxy-7-methyl-5H-furobenzopyran-5-one (Visnagin)

The photooxygenation of 4-methoxy-7-methyl-5H-furobenzopyran-5-one (Visnagin, 1) in methanol in absence and in presence of a sensitizer (methylene blue) has been studied. 6-Formyl-7-hydroxy-5-methoxy-2-methylchromone (4a), methyl 7-hydroxy-5-met

Copper(II) and Dioxouranium(VI) Complexes with Biologically Active Ligands: Part I - Complexes with Schiff Bases Derived from γ-Chromone

Copper(II) and dioxouranium(VI) complexes of some schiff bases derived from vesnagin and some amines have been prepared.These complexes have been charactrised on the bases of elemental analysis, UV, visible, infrared spectra and molar conductance data.It is concluded that the anions of the schiff bases are coordinated to the metal ions as bidentate ligands.