70384-80-4

Upstream product

• 635-93-8 5-chlorosalicyclaldehyde 
• 105-53-3 diethyl malonate 
• 18224-54-9 ethyl 3,3-bis(ethylsulfanyl)acrylate 
• 2033-24-1 cycl-isopropylidene malonate 
• 64-17-5 ethanol 
• 107-91-5 cyanoacetic acid amide 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 80415-73-2 3-carboxamido-4-(2'-oxocyclohexyl)coumarin 
• 80415-68-5 1-cyano-9-phenyl-1,2,3,4,4a,10b-hexahydro-5H-<1>-benzopyrano<3,4-c>pyridine-2,4,5-trione 
• 80415-66-3 8-benzylidene-2-chloro-10-cinnamoyl-6a,7,8,9,10,10a-hexahydro-6H-dibenzopyran-6,7,9-trione 
• 80415-62-9 2-Chloro-6,7,9-trioxo-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene-10-carboxylic acid N'-phenyl-hydrazide 
• 80415-64-1 2-Chloro-6,7,9-trioxo-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene-10-carboxylic acid benzylamide 
• 80415-59-4 2-Chloro-10-[1-(phenyl-hydrazono)-ethyl]-10,10a-dihydro-6aH-benzo[c]chromene-6,7,9-trione 

Relevant academic research and scientific papers

Synthesis, characterization and antioxidant activity studies of new coumarin tethered 1,3,4-oxadiazole analogues

The present work describes the synthesis of a series of substituted 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-ones 7(a–j) using substituted aldehydes with analogues of hydrazine hydrates by grinding technique in the presence of Iodine which helps in the cyclization process. The structures of the synthesized compounds were elucidated by spectroscopic techniques such as IR, 1H NMR, 13C NMR, and LCMS. The comparative antioxidant property (using DPPH and hydroxyl radical scavenging) has been studied with the synthesized compounds 7(a-j) and the standards. Compounds 7d and 7i show the prominent radical scavenging activity. Graphic abstract: [Figure not available: see fulltext.] Synopsis: Series of ten new coumarin-oxadiazole hybrids synthesized in three steps starting from salicylaldehyde and diethylmalonate. All new compounds were spectroscopically characterized. The results of radical scavenging activities show that, two compounds of the series 7d and 7i displayed potent DPPH and hydroxyl radical activity comparable to the standards employed, and therefore acts as antioxidant leads.

Coumarin derivatives act as novel inhibitors of human dipeptidyl peptidase III: Combined in vitro and in silico study

Dipeptidyl peptidase III (DPP III), a zinc-dependent exopeptidase, is a member of the metalloproteinase family M49 with distribution detected in almost all forms of life. Although the physiological role of human DPP III (hDPP III) is not yet fully elucida

A facile, efficient and solvent-free titanium (IV) ethoxide catalysed knoevenagel condensation of aldehydes and active methylenes

Titanium ethoxide has been employed as a novel and efficient reagent for the Knoevenagel condensation of aldehydes with active methylenes such as diethyl malonate and ethyl cyanoacetate under solvent free conditions to afford substituted olefins in high to excellent yields. The reaction is suitable for a variety of aromatic, aliphatic and heteroaromatic aldehydes with various active methylenes. Parallel to this, microwave irradiation has been utilized to achieve improved reaction rates and enhanced yields. Herein, we illustrated a convenient method for the preparation of α,β-unsaturated compounds using both conventional and microwave irradiation methods. An efficient and solvent free Knoevenagel condensation between aldehydes and active methylenes was developed using titanium ethoxide. The procedure proved to be successful with a wide range of substrates such as aromatic, aliphatic and heterocyclic aldehydes and various active methylenes to afford substituted olefins. The reaction was also carried out under microwave irradiation to accomplish the corresponding olefins with improved reaction rates, yields and cleaner reaction profiles.We have developed an efficient and novel methodology for the synthesis of olefinic compounds by Knoevenagel condensation under solvent-free conditions using titanium ethoxide, for the first time, as a reagent as well as a solvent. This method is appropriate for the synthesis of a variety of aromatic aldehydes containing various electron-donating and withdrawing groups, aliphatic and heteroaromatic aldehydes. The significant advantages offered by this methodology could be applied to various active methylenes in order to offer the corresponding Knoevenagel products. Thus, we believe that this method delivers high conversions, cleaner reaction profiles under solvent-free reaction conditions and shorter reaction times, all of which make it a very useful and attractive approach for the preparation of a wide range of substituted olefins.

Ros inhibitory activity and cytotoxicity evaluation of benzoyl, acetyl, alkyl ester, and sulfonate ester substituted coumarin derivatives

Background: A number of non-steroidal anti-inflammatory drugs (NSAIDs) including aspirin, indomethacin, ibuprofen, flufenamic acid, and phenylbutazone are being clinically used to treat inflammatory disorders. These NSAIDs are associated with serious side

A sustainable innovation for the tandem synthesis of sugar-containing coumarin derivatives catalyzed by lipozyme TL im from: Thermomyces lanuginosus in continuous-flow microreactors

We developed an efficient and environmentally friendly two-step tandem methodology for the synthesis of sugar-containing coumarin derivatives catalyzed by lipozyme TL IM from Thermomyces lanuginosus in continuous-flow microreactors. Compared to those observed for other methods, the salient features of this work including green reaction conditions, short residence time (50 min), and catalysts are more readily available and the biocatalysis reaction process is efficient and easy to control. This two-step tandem synthesis of coumarin derivatives using the continuous-flow technology is a proof of concept that opens the use of enzymatic microreactors in coumarin derivative biotransformations.

Design, synthesis and biological evaluation of coumarin-based N-hydroxycinnamamide derivatives as novel histone deacetylase inhibitors with anticancer activities

A series of novel coumarin-based N-hydroxycinnamamide derivatives were designed and synthesized as histone deacetylase (HDAC) inhibitors. Most of the synthesized compounds showed potent HDAC inhibitory activity and significant antiproliferative activity a

Synthesis and biological evaluation of carvacrol-based derivatives as dual inhibitors of H. Pylori strains and ags cell proliferation

This study reports on the synthesis, structural assessment, microbiological screening against several strains of H. pylori and antiproliferative activity against human gastric adenocarcinoma (AGS) cells of a large series of carvacrol-based compounds. Structural analyses consisted of elemental analysis,1 H/13 C/19 F NMR spectra and crystallographic studies. The structure-activity relationships evidenced that among ether derivatives the substitution with specific electron-withdrawing groups (CF3 and NO2) especially in the para position of the benzyl ring led to an improvement of the antimicrobial activity, whereas electron-donating groups on the benzyl ring and ethereal alkyl chains were not tolerated with respect to the parent compound (MIC/MBC = 64/64 μg/mL). Ester derivatives (coumarin-carvacrol hybrids) displayed a slight enhancement of the inhibitory activity up to MIC values of 8–16 μg/mL. The most interesting compounds exhibiting the lowest MIC/MBC activity against H. pylori (among others, compounds 16 and 39 endowed with MIC/MBC values ranging between 2/2 to 32/32 μg/mL against all the evaluated strains) were also assayed for their ability to reduce AGS cell growth with respect to 5-Fluorouracil. Some derivatives can be regarded as new lead compounds able to reduce H. pylori growth and to counteract the proliferation of AGS cells, both contributing to the occurrence of gastric cancer.

Supramolecular synthesis of coumarin derivatives catalyzed by a coordination-assembled cage in aqueous solution

A self-assembled Pd4L2 cage is employed as a water-soluble molecular flask for the synthesis of functionalized coumarins from a series of salicylaldehyde derivatives and cyanoacetates/malononitrile. The catalytic reaction features mild aqueous conditions and broad substrate scope. Crystal structures of the host-guest complexes for two substrates and one analogous intermediate have been obtained, shedding light on the supramolecular reaction mechanism. Michaelis-Menten kinetic studies were performed in one typical case, revealing that the rate of product formation has been enhanced by over 23-fold in contrast to the background reaction without cage. Moreover, the same reaction catalyzed by a smaller Pd6L4 cage gives a mixture of products and much lower yields, suggesting that fine-tuning on the size and symmetry of the cages’ cavity is crucial for their applications in supramolecular catalysis.

Solvent-Free FeCl3-Assisted Electrophilic Fluorine-Catalyzed Knoevenagel Condensation to Yield α,β-Unsaturated Dicarbonyl Compounds and Coumarins

A highly environmentally friendly procedure was developed for the Knoevenagel condensation of aromatic aldehydes with diethyl malonate in the presence of FeCl3 and N-fluorobenzenesulfonimide as a source of electrophilic fluorine under solvent-free conditions. The scope of the reaction was explored using commercially available substrates. The reaction with substituted salicylaldehydes afforded the corresponding coumarin derivatives which attract interest due to their potential medicinal importance.

Evaluation of novel N′-(3-hydroxybenzoyl)-2-oxo-2H-chromene-3-carbohydrazide derivatives as potential HIV-1 integrase inhibitors

In an attempt to identify potential new agents that are active against HIV-1 IN, a series of novel coumarin-3-carbohydrazide derivatives were designed and synthesised. The toxicity profiles of these compounds showed that they were non-toxic to human cells and they exhibited promising anti-HIV-1 IN activities with IC50 values in nM range. Also, an accompanying molecular modeling study showed that the compounds bind to the active pocket of the enzyme.