33265-15-5

Upstream product

• 33259-48-2 3-acetamido-8-methoxy-2H-chromen-2-one 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 4283-57-2 8-methoxy-3-aminocoumarin 

Downstream Products

• 131575-56-9 Trifluoro-methanesulfonic acid 4-(2,5-dimethoxy-phenyl)-8-methoxy-2-oxo-2H-chromen-3-yl ester 
• 131575-55-8 Trifluoro-methanesulfonic acid 8-methoxy-4-(4-methoxy-phenyl)-2-oxo-2H-chromen-3-yl ester 
• 131575-60-5 4-(2,5-Dimethoxy-phenyl)-8-methoxy-chromen-2-one 
• 131575-59-2 8-methoxy-4-(4-methoxyphenyl)-2H-chromen-2-one 
• 155620-97-6 3-(benzyloxycarbonyloxy)-8-methoxy-1-benzopyran-2-one 
• 131575-50-3 4-(2,5-Dimethoxy-phenyl)-3-hydroxy-8-methoxy-chromen-2-one 
• 131575-49-0 4-(2,4-Dimethoxy-phenyl)-3-hydroxy-8-methoxy-chromen-2-one 
• 131575-48-9 3-Hydroxy-8-methoxy-4-(4-methoxy-phenyl)-chromen-2-one 
• 131575-47-8 3-Hydroxy-8-methoxy-4-phenyl-chromen-2-one 

Relevant academic research and scientific papers

Novel coupled molecules from active structural motifs of synthetic and natural origin as immunosuppressants

Introduction: Nitric oxide (NO) is an important mediator in the pathogenesis and control of immune system-related disorders and its levels are modulated by inducible NO synthase (iNOS). Oxidative stress is another pathological indication in majority of autoimmune disorders. The present study aims at the development of coupled molecules via selection of pharmacophores for both immunomodulatory and antioxidant activities through iNOS inhibition. Methods: Variedly substituted coumarin moieties are coupled with naturally occurring phenols through an amide linkage and were predicted for activities using computer-based program PASS. The compounds predicted to have dual activities were synthesized. Docking studies were carried out against iNOS (PDB 1R35) and compounds having good docking score were evaluated for immunomodulatory and antioxidant activities. Results: The synthesized compounds were found to be pure and were obtained in good yields. Compounds with maximum docking score (YR1a, YR2e, YR2c and YR4e) were selected for evaluation by in vitro models. Compounds YR2e and YR2c markedly inhibited the reduction of NBT dye and showed maximum percent iNOS inhibition. In DPPH assay, compound YR4e was observed as the most potent antioxidant (EC50 0.33 μM/mL). Based on these studies, compounds YR2e and YR2c were selected for haemagglutination test. Compound YR2e was observed as the most active immunosuppressant with maximal inhibitory ability of iNOS and NBT reduction and lower HAT value of 3.5. Conclusion: Compound YR2e can be utilized as a pharmacological agent in the prevention or treatment of immunomodulatory diseases such as tumors, rheumatoid arthritis, ulcerative colitis, organ transplant and other autoimmune disorders.

A novel class of human 15-LOX-1 inhibitors based on 3-hydroxycoumarin

Inflammations, sensitivities, and some cancers in mammals are intimately linked to the activity of lipo-oxygenase enzymes. Owing to the importance of these enzymes, mechanistic studies, product analysis, and synthesis of inhibitors have expanded. In this study, a series of hydroxycoumarins, methoxy-3-hydroxy coumarins, and 7-alkoxy-3-hydroxy coumarins were synthesized and evaluated as potential inhibitors of human 15-LOX-1. Among the synthetic coumarins, 7-methoxy-3-hydroxycoumarin derivative demonstrated potent inhibitory activity and the compound, 5f, showed the best result. Radical scavenging assessment, IC50, HNMR, and DPPH bleaching results indicate that the electronic properties are the major factors for the lipo-oxygenase inhibition potency of the synthetic coumarins. Based on the theoretical studies, it was suggested that the mesomeric effect of the substituent at the seventh position of the benzene ring is one of the major factors in the stability of the oxy-radical intermediate.

New efficient synthesis of pyrido[2,3-c] and pyrido[3,2-c]coumarin derivatives

Various substituted pyrido[2,3-c] and pyrido[3,2-c]coumarins are efficiently prepared in three steps from 3- and 4-hydroxycoumarins, respectively and protected β-aminoketones.

Reaction of aryl-2-hydroxypropenoic derivatives with boron tribromide

(Z)-Mono, di or trimethoxyphenyl-2-hydroxypropenoic acids 1a-d gave mixtures of (E) and (Z) mono, di or trihydroxyphenyl-2-hydroxypropenoic acids 2a-d when treated with boron tibromide. The isomerisation proceeds during the work-up and depends on the duration of the hydrolysis and the number of oxygens on the aromatic ring. When the aromatic ring was substituted with a methoxy group at the ortho position, a cyclisation occurs, and 3-hydroxycoumarins 3 and benzofuran-2-carboxylic acids 4 can be obtained. 3-Hydroxycoumarin 3a can also be obtained almost quatitatively from the reaction of methyl 3-(2-methoxyphenyl)-2,3-epoxypropanoate with boron tribromide.

[(4-Oxo-4H-1-benzopyran-3-yl)oxy] acetic acids and derivatives

Compounds of formula I: STR1 wherein Y is hydrogen, lower alkyl, halogen or lower alkoxy; X is carboxy, alkoxycarbonyl, carboxamide, cyano or tetrazolo, and their non-toxic, pharmaceutically acceptable salts are disclosed. These compounds are useful in the prevention of allergic and asthmatic reactions.