77117-15-8

Upstream product

• 860253-97-0 2-(2-hydroxy-5-methyl-benzyl)-acetoacetic acid-lactone 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 626-34-6 ethyl aminocrotonate 

Downstream Products

• 1258231-93-4 3-(2-hydroxyphenyl)-6-(6-methyl-2-oxochromen-3-yl)-7H[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 1258231-95-6 6-(6-methyl-2-oxochromen-3-yl)-3-(3-methylphenyl)-7H[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 1258231-97-8 3-(4-chlorophenyl)-6-(6-methyl-2-oxochromen-3-yl)-7H[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 

Relevant academic research and scientific papers

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Synthesis and antiproliferative activity of hybrid thiosemicarbazone derivatives bearing coumarin and d-galactose moieties with EGFR inhibitory activity and molecular docking study

A series of substituted N-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)thiosemicarbazones 5a–5j of substituted 3-acetylcoumarins were synthesized with yields of 45–68%. All synthesized thiosemicarbazones were evaluated for cytotoxic activity against several cancer cell lines, such as human breast adenocarcinoma cells MCF7, human liver cancer cells HepG2, human cervical cancer cells HeLa, human melanoma cancer cells SK-Mel-2, and human lung cancer cells LU-1 by using the standard MTT assay. The IC50 values for these cancer cell lines were 1.28–11.81 μM (for MCF-7), 1.53–22.12 μM (for HepG2), 1.43–48.16 μM (for HeLa), 1.82–14.62 μM (for SK-Mel-2), and 1.74–14.62 μM (for LU-1). Most of the compounds were noncytotoxic against human WI-38 normal cell line (IC50 > 16.9 μM). The antiproliferative mechanisms were studied via EGFR inhibition and molecular docking. Docking studies revealed that there are strong interactions between a typical compound with the receptor of the EGFR tyrosine kinase domain with Erlotinib. [Figure not available: see fulltext.]

Synthesis and biological screening of thiosemicarbazones of substituted 3-acetylcoumarins having D-glucose moiety

Thiosemicarbazones 5a-j were synthesized with yields of 45–68% by condensation of 3-acetylcoumarins 3a-j and tetra-O-acetyl-β-D-thiosemicarbazide 4. All obtained thiosemicarbazones were screened for anti-microorganic activities against bacteria (B. subtilis, S. aureus, S. epidermidis, E. coli, P. aeruginosa, K. pneumoniae, S. typhimurium) and fungi (A. niger, C. albicans, S. cerevisiae, and A. flavus). Some compounds had significant inhibitory activity with MICs of 0.78–3.125 μM in comparison with 5a, including 5e,h,i for S. aureus, and 5c,f,i for S. epidermidis (Gram-(+) bacteria), 5c,f,g for E.coli, 5f for K. pneumoniae, 5b,c,g for P. aeruginosa, and 5i for S. typhimurium (Gram-(?) bacteria), 5d,h,i for A. niger, 5i for A. flavus, 5b,d,e,h for C. albicans, and 5i for S. cerevisiae. Compounds exhibited excellent activity against tested microorganism with MIC = 0.78 μM, including 5h,i (against S. aureus), 5h (against C. albicans), and 5i (against S. cerevisiae).

Synthesis and characterisation of novel 3-(4-benzoyl-5-phenylfuran-2-yl) coumarins

Novel 3-(4-benzoyl-5-phenylfuran-2-yl)coumarin derivates were synthesised via a simple three-step reaction from salicylic aldehydes, ethyl 3-oxobutanoate and 1,3-diphenylpropane-1,3-dione. The synthesised compounds were characterised by NMR, MS and elemental analyses and single-crystal X-ray diffraction analysis.

Green and Rapid Access to Benzocoumarins via Direct Benzene Construction through Base-Mediated Formal [4+2] Reaction and Air Oxidation

Benzocoumarin is an important structural motif widely found in natural products and synthetic molecules. Traditional methods for the synthesis of benzocoumarins and their derivatives require multiple steps, typically with an intramolecular ester forming reaction to make the lactone ring as the last step. Another major method involves transition metal-catalyzed coupling or carbon-hydrogen bond activation reactions starting with pre-existing aryl frameworks in the substrates. Here we report a new strategy for the green and rapid access to benzocoumarins and their derivatives. Our method uses readily available unsaturated aldehydes and coumarins as the substrates and air as the green oxidant. The overall reaction proceeds through a formal [4+2] process to construct a new benzene ring and thus to afford benzocoumarins in essentially a single step. No metal catalysts were used; no toxic or expensive reagents were involved. The power of our new approach is further demonstrated in a concise formal total synthesis of cannabinol, a bioactive natural product.

New two-photon absorption benzotriazole-coumarin dyads: The evidence of internal proton transfer in the excited state

New near-infrared two-photon absorption π-extended benzotriazole-coumarin dyads as target molecules were synthesized. The corresponding coumarin derivatives and esterified dyads were also prepared as the references. The experimental evidence of internal p

Novel 2H-chromen derivatives: Design, synthesis and anticancer activity

A series of novel dihydropyrazole derivatives linked with 2H-chromen were designed and synthesized. All of the compounds have been screened for their antiproliferative activity against MGC-803, Bcap-37, SGC-7901 and HepG 2 cell lines in vitro. The results revealed that compounds 4a and 10a exhibited strong inhibitory activity against HepG2 cell and manifested obvious un-toxic effect on GES-1 and L-02 cell lines. Some title compounds were tested against telomerase, compound 10a showed the most potent inhibitory activity with IC50 value at 0.98 ± 0.11 μM, it could fit well into the active site of TERT. The further molecular mechanism of antiproliferation was explored, the data suggested that compound 10a could inhibit hTERT expression and Wnt/β-catenin signaling.

Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives

Several 3-carbonyl (1-26), 3-acyl (27-52), and 3-carboxyhydrazido (53-58) coumarins have been synthesized in high yields (72-99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.

Preparation and synthetic use of polymer-supported acetoacetate reagent

Coumarin synthesis using polymer-supported acetoacetate reagent was carried out to produce various coumarin derivatives in excellent yield and purity with a facile work-up process. It was found that the polymer reagent could be recycled without any diminishment of the yield and purity. Georg Thieme Verlag Stuttgart.

A Novel Pentacyclic Pyridine Dilactone. 7-Methylbenzopyranobenzoxacinopyridine-6,16-dione

When equimolar quantities of salicylaldehyde 2 and ethyl 3-amino-2-butenoate 3 or its constituents (ethyl 3-oxobutanoate and ammonia) were refluxed on a steam-bath for 6 hours with a trace of acetic acid, two products, a pentacyclic pyridine dilactone 4 and 3-acetyl coumarin 5, resulted in 15percent and 45percent yields, respectively.The structure of 4 was elucidated as 7-methylbenzopyranobenzoxacinopyridine-6,16-dione on the basis of its spectral data.The mechanism of its formation has been discussed.The reaction has been extended to three more substituted salicylaldehydes.