57339-72-7

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 2555-37-5 3-acetyl-4-hydroxychromen-2-one 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 2748-33-6 3-[4,5-dihydro-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]-4-hydroxy-2H-chromen-2-one 
• 1228758-77-7 4,5-dihydro-3-(4-hydroxy-2-oxo-2H-chromen-3-yl)-5-(4-methoxyphenyl) pyrazol-1-carbothioamide 
• 2748-28-9 4-hydroxy-3-[5-(4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]coumarin 

Relevant academic research and scientific papers

Antileishmanial activity of novel indolyl-coumarin hybrids: Design, synthesis, biological evaluation, molecular docking study and in silico ADME prediction

In present work we have designed and synthesized total twelve novel 3-(3-(1H-indol-3-yl)-3-phenylpropanoyl)-4-hydroxy-2H-chromen-2-one derivatives 13(a-l) using Ho3+doped CoFe2O4nanoparticles as catalyst and evaluated for their potential antileishmanial and antioxidant activities. The compounds 13a, 13d and 13h were found to possess significant antileishmanial activity (IC50value = 95.50, 95.00 and 99.00 μg/mL, respectively) when compared to the standard sodium stibogluconate (IC50= 490.00 μg/mL). The compounds 13a (IC50= 12.40 μg/mL), 13d (IC50= 13.49 μg/mL), 13g (IC50= 13.24 μg/mL) and 13l (IC50= 13.74 μg/mL) had shown good antioxidant activity when compared with standards butylated hydroxy toluene (IC50= 16.5 μg/mL) and ascorbic acid (IC50= 12.8 μg/mL). After performing molecular docking studies, it was found that compounds 13a and 13d had potential to inhibit pteridine reductase 1 enzyme. In silico ADME pharmacokinetic parameters had shown promising results and none of the synthesized compounds had violated Lipinski's rule of five. Thus, suggesting that compounds from the present series can serve as important gateway for the design and development of new antileishmanial as well as antioxidant agent.

Chalcone-based derivatives as new scaffolds for hA3 adenosine receptor antagonists

Objectives With the aim of finding new adenosine receptor (AR) ligands based on the chalcone scaffold, we report the synthesis of a new series of coumarin-chalcone hybrids and the pharmacological characterization of their actions at four subtypes of AR. Methods The synthesized compounds 5-10 were characterized in radioligand binding (A1, A2A and A 3) and adenylyl cyclase activity assays (A2B) to determine the affinity of the compounds for the four human AR (hAR) subtypes. Key findings Coumarin-chalcone hybrids were found to be ligands with a novel structure, not reported thus far, that showed varying affinity and selectivity for AR subtypes. Conclusions The coumarin-chalcone hybrids in which ring B of the chalcone scaffold was a thiophene (compounds 5 and 9) were found to be the most potent compounds of the series. Compound 9, in which ring A of the chalcone moiety was the phenyl ring of the coumarin, showed similar activity against hA1, hA2A and hA3 ARs, while compound 5, in which ring A of the chalcone was substituted by the benzopyrone ring of the coumarin moiety, showed similar activity only at the hA3 AR and, therefore, was deemed to be selective (Ki (dissociation constant) = 5160 nm). A new series of chalcone-based derivatives, including a coumarin moiety in their structures, have been synthesized and binding assays for the hA1, hA2A, and hA3 adenosine receptors were employed to assess the affinity for receptor subtypes. Isosterical substitutions of one or both phenyl rings of the chalcone moiety reveal that thiophene-containing compounds 5 and 9 have good binding affinity for ARs. Compound 5, in which both phenyl rings of the original chalcone scaffold (rings A and B) were substituted for a thiophene and pyrone rings, resulted selective for the hA3 adenosine receptor (Ki = 5,160 nM). Based on the obtained results, a preliminary structure-activity relationship (SAR) study showed a high selectivity and good potency of these thiophene-containing compounds. 2013 The Authors. JPP

Design, synthesis and biological evaluation of some novel 3-cinnamoyl-4-hydroxy-2H-chromen-2-ones as antimalarial agents

A novel series of 3-cinnamoyl-4-hydroxy-2Hchromen-2-ones were designed, synthesized and screened for antiplasmodial activity. Eleven compounds of the series exhibited micromolar potency against chloroquine sensitive and chloroquine resistant strains. The most potent compound 4-hydroxy-3-(3-(4- nitrophenyl)acryloyl)-2Hchromen-2-one showed inhibitory potency (IC 50) of 3.1 and 4 μg/ml against chloroquine sensitive and chloroquine resistant strains, respectively. A structure activity relationship study was performed by correlating the effect of substituents with the antimalarial activity of the title compounds. The novel 3-cinnamoyl-4-hydroxy- 2H-chromen-2-ones reported here should be good lead for further development of antimalarial agents that can overcome resistance.

Evaluation of Structurally Diverse Benzoazepines Clubbed with Coumarins as Mycobacterium tuberculosis Agents

Tuberculosis caused by Mycobacterium tuberculosis remains a leading cause of mortality worldwide into 21st century. In continuation with our anti-tuberculosis research programme, in this work, we have prepared molecularly diverse coumarins clubbed with benzothiazepines as well as its aza-analogues-benzodiazepines by molecular hybridization. The resulting compounds were screened for their M. tuberculosis activity against H37Rv strains using microplate alamar blue assay. Among the designed diversity, the compounds 5k, 5n and 5o were found significantly active in primary anti-tuberculosis assay at minimum inhibitory concentration 50 values of 5k and 5o in level-2 screening were observed as >10μg/mL and 3.63μg/mL, respectively. Design and synthesis of more focused library and its three-dimensional quantitative structure activity relationship analysis are underway. In the present work, various coumarins clubbed with benzo(thi)diazepines were evaluated for their M. tuberculosis activity against H37Rv strains using MABA assay. The IC50 values of two analogs (compounds 5k and 5o) in level-2 screening were observed as >10μg/mL and 3.63μg/mL respectively.

Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives

The action of the coumarin-type drugs and related compounds is reviewed to their VKOR antagonistic effects. In our study, twenty 3-pyridinyl, pyrimidinyl and pyrazolyl-4-hydroxycoumarin derivatives were synthesized. A comparative in vivo (CT, PT determination) and in vitro (measurement of PIVKA-II levels) anticoagulant study with respect to warfarin showed that the synthesized compounds have different anticoagulant activities, the most prospective compounds were the 3-pyrazolyl-4-hydroxycoumarin derivatives.