65692-17-3

Upstream product

• 1983-81-9 4,7-dihydroxycoumarin 
• 74-88-4 methyl iodide 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 17575-15-4 4-hydroxy-7-methoxycoumarine 
• 67-56-1 methanol 
• 108-46-3 recorcinol 
• 244049-27-2 4-amino-7-hydroxy-2H-chromen-2-one 

Downstream Products

• 1314133-73-7 4-methoxy-7-[2-(4-phenylpiperazin-1-yl)ethoxy]-2H-chromen-2-one 
• 1314133-74-8 4-methoxy-7-{2-[4-(4-methylphenyl)piperazin-1-yl]ethoxy}-2H-chromen-2-one 
• 1314133-75-9 4-methoxy-7-{2-[4-(2-methylphenyl)piperazin-1-yl]ethoxy}-2H-chromen-2-one 
• 1314133-76-0 4-methoxy-7-{2-[4-(4-methoxyphenyl)piperazin-1-yl]ethoxy}-2H-chromen-2-one 
• 1314133-77-1 4-methoxy-7-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxy}-2H-chromen-2-one 
• 1314133-78-2 7-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethoxy}-4-methoxy-2H-chromen-2-one 
• 1314133-79-3 7-{3-[4-(4-chlorophenyl)piperazin-1-yl]propoxy}-4-methoxy-2H-chromen-2-one 
• 1314133-80-6 7-{4-[4-(4-chlorophenyl)piperazin-1-yl]butoxy}-4-methoxy-2H-chromen-2-one 
• 482647-23-4 4-hydroxy-7-{3-[4-(p-nitrophenyl)-1-piperazinyl]propyloxy}coumarin 
• 482647-21-2 4-methoxy-7-{3-[4-(4-nitro-phenyl)-piperazin-1-yl]-propoxy}-chromen-2-one 
• 482647-39-2 4-methoxy-7-{3-[4-(4-methoxy-phenyl)-piperazin-1-yl]-propoxy}-chromen-2-one 

Relevant academic research and scientific papers

Synthesis and cytotoxic activities of novel 4-methoxy-substituted and 5-methyl-substituted (3′S,4′S)-(-)-cis-khellactone derivatives that induce apoptosis via the intrinsic pathway

This study deals with the design and synthesis of a series of novel 4-methoxy-substituted and 5-methyl-substituted (3′S,4′S)-(-)-cis-khellactones. The newly synthesized compounds were characterized by1H nuclear magnetic resonance (NMR),13

Multi-target tacrine-coumarin hybrids: Cholinesterase and monoamine oxidase B inhibition properties against Alzheimer's disease

A series of novel tacrine-coumarin hybrids were designed, synthesized and evaluated as multi-target agents against Alzheimer's disease. The biological assays indicated that most of compounds displayed potent inhibitory activity toward AChE and BuChE, and clearly selective inhibition for MAO-B. Among these compounds, 14c exhibited strong inhibitory activity for AChE (IC50 values of 33.63 nM for eeAChE and 16.11 nM for hAChE) and BuChE (IC50 values of 80.72 nM for eqBuChE and 112.72 nM for hBuChE), and the highest inhibitory activity against hMAO-B (IC50 value of 0.24 11/4M). Kinetic and molecular modeling studies revealed that 14c was a mixed-type inhibitor, binding simultaneously to catalytic, peripheral and mid-gorge sites of AChE. It was also a competitive inhibitor, which covered the substrate and entrance cavities of MAO-B. Moreover, 14c could penetrate the CNS and show low cell toxicity. Overall, these results suggested that 14c might be an excellent multi-target agent for AD treatment.

Synthesis of osthole derivatives with grignard reagents and their larvicidal activities on mosquitoes

The structure of osthole has been modified to improve its larvicidal activity against mosquitoes. A new efficient synthesis of osthole derivatives with Grignard reagents has been developed, which employs CuI and LiCl as promoters and covers a broad range of substrates to afford the corresponding products in mild to good yields (up to 83%). Bio-activity evaluation showed that several products exhibited better activities than osthole. CuI and LiCl promoted efficient synthesis of osthole derivatives with Grignard reagents has been developed. Bio-activity evaluation showed that several products exhibited far better larvicidal activities against mosquitoes than osthole.

Design, synthesis and evaluation of novel tacrine-coumarin hybrids as multifunctional cholinesterase inhibitors against Alzheimer's disease

A series of tacrine-coumarin hybrids (8a-t) were designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit ChE and self-induced β-amyloid (Aβ) aggregation, and to act as metal chelators. Especially, 8f displayed the greatest ability to inhibit acetylcholinesterase (AChE, IC50 = 0.092 μM) and Aβ aggregation (67.8%, 20 μM). It was also a good butyrylcholinesterase inhibitor (BuChE, IC50 = 0.234 μM) and metal chelator. Besides, kinetic and molecular modeling studies indicated that 8f was a mixed-type inhibitor, binding simultaneously to active, peripheral and mid-gorge sites of AChE. These results suggested that 8f might be an excellent multifunctional agent for AD treatment.

Energy transfer in coumarin-sensitised lanthanide luminescence: Investigation of the nature of the sensitiser and its distance to the lanthanide ion

A series of lanthanide complexes [Ln(dpxCy)3]3- have been synthesised. The ligands are composed of a coordinating dipicolinic acid backbone decorated with a polyoxyethylene arm fitted with a coumarin moiety at its extremity. The nature of the coumarin as well as the length of the linker have been varied. Upon excitation at 320 nm, the coumarin exclusively acts as an antenna while the dipicolinic acid core is not excited. Upon excitation below 300 nm, both parts are excited. With europium as a metal centre, the relaxation of the europium ion (intrinsic quantum yield ΦEuEu and radiative lifetime τr) is constant for all the studied ligands. Therefore, the observed differences in overall quantum yield (ΦEuL) in such systems come exclusively from the variation of the terminal coumarin. The overall quantum yields of the studied complexes are low (ΦEuL sens), the distance between the coumarin sensitiser and the lanthanide centre was explored in solution and compared to the solid state. In the solid state, a dramatic effect was confirmed, with an improvement of 80% in the quantum yield ΦEuL for short linkers ((-CH2CH2O-)n with n = 1 compared to n = 3). By monitoring the lifetime decay of the excited state of the lanthanide cation with nanosecond vs. microsecond time-resolved spectroscopy at low temperature, the sensitisation of the lanthanide ions by coumarin derivatives was demonstrated to mainly occur through the singlet excited state of the coumarin and not via the usual triplet pathway. No evidence of a different behaviour at room temperature was found by transient triplet-triplet absorption spectroscopy.

Rational design, synthesis, biological evaluation, homology and docking studies of coumarin derivatives as α1-adrenoceptor antagonists

According to a three-point pharmacophore for some uro-selective α1-adrenoceptor (AR) antagonists, a novel class of coumarin (=2H-1-benzopyran-2-one) derivatives have been successfully designed and synthesized with high efficacies for α1/s

Hydroxycoumarin derivatives: Novel and potent α-glucosidase inhibitors

A novel class of hydroxycoumarin derivatives were found to be potent α-glucosidase inhibitors. Their syntheses were reported and the structure-activity relationship was established. Kinetic enzymatic assays indicated that compound 10 was a slow-binding and noncompetitive inhibitor with a Ki value of 589 nM, while compound 11 was a competitive inhibitor with a Ki value of 4.810 μM. Among all hydroxycoumarin derivatives studied, compounds 10 and 11 exhibited the highest activities, were specific inhibitors of α-glucosidase, and could be exploited as the lead compounds for the development of potent α-glucosidase inhibitors. Compounds 10 and 11 were also selected for further discussion for the mechanism of enzymatic inhibition.

BENZOPYRONE COMPOUNDS, PREPARATION METHOD AND USE THEREOF

The invention relates to pesticide and bactericide, specifically to the benzopyrone compounds and its preparation method and use thereof. The benzopyrone compounds of the invention having general formula (I): The present invention, having good pesticide activity and broad bactericide activity, applied for controlling various pests in plants such as army worm, diamond backmoth and aphid, carmine spider mite, two-spotted spider mite, ladybeetle, mites and mosquito larvae. Various disease in plants can be controlled by the invention and that of grape downy mildew, rice sheath and culm blight, rice blast, tomato early blight, tomato late blight ,wheat leaf rust, wheat leaf blotch, wheat powdery mildew, cucumber powdery mildew, cucumber downy mildew, cucumber grey mold and so on.

Synthesis and characterization of some coumarins with two hydroxy or methoxy substituents

The first synthesis of the 6-hydroxy-4-methoxycoumarin (5) was carried out in 25% overall yield from 6-methoxy-4-hydroxycoumarin (1) by hydrolysis of the methoxy group and subsequent selective methylation of the hydroxyl group at position 4. The 1H and 13C NMR data of compounds 1-6 are reported.

Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents

To explore the structural requirements of (+)-cis-khellactone derivatives as novel anti-HIV agents, 24 monosubstituted 3',4'-di-O-(S)- camphanoyl-(+)-cis-khellactone (DCK) derivatives were synthesized asymmetrically. These compounds included 4 isomeric monomethoxy analogues (3- 6), 4 isomeric monomethyl analogues (7-10), 4 4-alkyl/aryl-substituted analogues (11-14), and 12 4-methyl-(+)-cis-khellactone derivatives (15-26) with varying 3',4'-substituents. These (+)-cis-khellactone derivatives were screened against HIV-1 replication in acutely infected H9 lymphocytes. The results demonstrated that the (3'R,4'R)-(+)-cis-khellactone skeleton, two (S)-(-)-camphanoyl groups at the 3'- and 4'-positions, and a methyl group on the coumarin ring, except at the 6-position, were optimal structural moieties for anti-HIV activity. 3-Methyl- (7), 4-methyl- (8), and 5-methyl- (9) 3',4'- di-O-(S)-camphanoyl-(3'R,4'R)-(+)-cis-khellactone showed EC50 and therapeutic index values of -5 μM and >2.15 x 106, respectively, in H9 lymphocytes, which are much better than those of DCK and AZT in the same assay. Furthermore, 8 and 9 also showed potent inhibitory activity against HIV-1 replication in the CEM-SS cell line, and most monosubstituted DCK analogues were less toxic than DCK in both assays.