53653-67-1

Upstream product

• 141-97-9 ethyl acetoacetate 
• 97-51-8 5-Nitrosalicylaldehyde 
• 105-45-3 acetoacetic acid methyl ester 
• 61-82-5 3-amino-1,2,4-triazole 

Downstream Products

• 1215211-10-1 C₂₆H₁₉N₅O₅ 
• 1260653-70-0 C₂₅H₁₆FN₅O₄ 
• 133632-88-9 3-methyl-8-nitro-1-phenylchromeno[4,3-c]pyrazol-4-(1H)-one 

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 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 antiproliferative evaluation of novel biheterocycles based on coumarin and 2-aminoselenophene-3-carbonitrile unit

A series of novel coumarins with 2-amino-3-cyanoselenophen-5-yl unit on C-3 have been synthesized. These compounds prepared easily at room temperature, in a short time and in high yield. The importance of biheterocyclic units as dominant structural motif of coumarin derivatives has been well recognized. Anti-cancer activity screening on MCF-7 cell line allowed identification of 2-amino-5-(6-bromo-2-oxo-2H-chromen-3-yl)selenophene-3-carbonitrile with the highest level of cytotoxic activity with mean IC50 and cLogP (partition co-efficient) values 10.84 μM and 3.18, respectively. The most radical scavenging compound was also recognized. Graphic abstract: [Figure not available: see fulltext.].

Pyrazole–coumarin and pyrazole–quinoline chalcones as potential antitubercular agents

Pyrazole, coumarin, and quinoline are medicinally important moieties. In this study, two series of novel pyrazole–coumarin chalcones and pyrazole–quinoline chalcones were synthesized using multiple-step reactions. All the synthesized compounds were well c

Regioselective hydrodehalogenation of aromatic α-and β-halo carbonyl compounds by cui in isopropanol

An operationally efficient and regioselective hydrodehalogenation methodology of aromatic α-and β-halo carbonyl compounds has been developed using CuI in isopropanol at 90 °C under basic condition. The catalytic system effectively dehalogenates chloride, bromide, and iodide groups and af-forded high yield (up to 97 %) as carbonyl compounds. The methodology is environmentally friendly and demonstrates excellent tolerance to a broad range of electronically rich and poor substituents.

Structural investigations on coumarins leading to chromeno[4,3-c]pyrazol-4-ones and pyrano[4,3-c]pyrazol-4-ones: New scaffolds for the design of the tumor-associated carbonic anhydrase isoforms IX and XII

Human carbonic anhydrases (hCAs, EC 4.2.1.1) IX and XII are overexpressed in a wide variety of cancers and are considered available drug targets for anti-tumor therapy since their inhibition has been shown to reduce tumor growth and metastasis. A set of coumarin derivatives (1–10) and several 1-aryl and 2-aryl-substituted chromeno[4,3-c]pyrazol-4-ones (11–37) and pyrano[4,3-c]pyrazol-4-ones (38–39) were synthesized and tested against the tumor-associated hCAs IX and XII and the cytosolic isoforms hCAs I and II. Several compounds were potent (Ki i = 5.6–9.6 nM), while none were effective against the off-target cytosolic hCAs I and II. Some selected inhibitors (6, 11, 13, 19, 21, 25, 31 and 39) showed activity as antiproliferative agents on HT-29 colon cancer cell lines both in normoxic and hypoxic conditions. This finding led us to hypothesize for these derivatives more than one mechanism of action, involving hCAs IX and XII inhibition in hypoxia and other not identified target(s) in normoxia.

Synthesis, X-ray crystallographic study, pharmacology and docking of hydrazinyl thiazolyl coumarins as dengue virus NS2B/NS3 serine protease inhibitors

A series of total twenty-one thiazole-coumarin derivatives 7a-u, linked via hydrazine linkage were synthesized through Hantzsch cyclisation. Out of twenty-one derivatives, fourteen derivatives viz. 7b-d, 7g, 7i-k, 7n and 7p-u are the novel derivatives. The structures of the synthesized compounds were established by extensive spectroscopic studies (FTIR, 1H NMR, 13C NMR, 2D NMR, LC-MS) and elemental analysis. The structure of (E)-6-methoxy-3-(1-(2-(4-p-tolylthiazol-2-yl)hydrazono)ethyl)-2H-chromen-2-one (7d) was unambiguously confirmed by X-ray crystallography analysis. Hybrid molecules were evaluated for their potential as anti-tubercular agents against Mycobacterium tuberculosis H37Rv ATCC 25618, and anti-bacterial agents against Eschericia coli, Enterobacter aerogenes, Salmonella typhi, Streptococcus pneumoniae and Staphylococcus aureus. All the compounds displayed considerable potency against all the pathogens with MIC values ranging from 31.25 to 250 μg/mL, therein compounds 7i, 7j, 7k, 7q and 7t displayed superior inhibitory activities compared to standard drugs streptomycin, kanamycin, vancomycin and isoniazid. Molecular docking studies were performed to check the potential as dengue virus NS2B/NS3 serine protease inhibitors, by comparing to standards 4-hydroxypanduratin, panduratin and ethyl 3-(4-(hydroxymethyl)-2-methoxy-5-nitrophenoxy)propanoate with DS of ?3.379, ?3.189 and ?3.381, respectively. All the compounds were found to exhibit potency against the DENV virus. In particular, compound 7c (DS –5.141) and 7l (DS –3.894) were found to be even better than the standards followed by compounds 7j (DS –3.113) and 7q (DS –3.561).

Microwave-assisted efficient and convenient one-pot synthesis of novel 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins under solvent-free conditions

[Figure not available: see fulltext.] An efficient green synthesis of novel 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins has been developed. One-pot reaction of 3-acetylcoumarin, malononitrile, and elemental sulfur, catalyzed by L-proline, resulted in the formation of thiophene derivatives, which were used as precursors for the synthesis of 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins. Target compounds were prepared by a one-pot method or stepwise, and NH4OAc was exploited as a reagent and molten salt. Microwave irradiation method was successfully applied to afford the products in excellent yields.

Tetrabutylammonium tribromide: An effective green reagent for the one-pot reaction of 3-acetyl-2H-chromen-2-ones with o-phenylenediamines

An efficient and completely greener approach has been outlined for the reaction of 3-acetyl-2H-chromen-2-ones with o-phenylenediamines using tetrabutylammonium tribromide (TBATB) to obtain 3-(quinoxalin-2-yl)-2H-chromen-2-ones in one-pot. Alternatively, a step-wise method has also been demonstrated for the synthesis of 3-(quinoxalin-2-yl)-2H-chromen-2-ones, where 3-acetyl-2H-chromen-2-ones has first treated with TBATB to give 3-(2-bromoacetyl)-2H-chromen-2-one followed by its nucleophilic substitution reaction with o-phenylenediamines. Use of polyethylene glycol-600 (PEG-600) as the solvent media, mild reaction conditions and easy isolation procedure of products are the added advantages for this synthesis. Both the one-pot and step-wise methods have been compared in terms of their reaction yields and one-pot synthesis was found to be superior. All the synthesized compounds were confirmed by characterization with 1HNMR, 13CNMR, HRMS, IR spectroscopy.

Development of hydrogelator-based gel-entrapped base catalysts (GEBCs) as heterogeneous basic catalysts for the synthesis of 3-acetylcoumarins

New gel entrapped base catalysts (GEBCs) have been prepared by entrapping some organic and inorganic bases into a solid aqueous gel matrix. Sodium alginate, gelrite and carboxymethyl chitosan were studied for the preparation of GEBCs. The phase behaviour of binary systems (gelator + water) is well studied, but ternary systems (gelator + water + base) are not much studied. Addition of a base to a (gelator + water) system drastically affected the behaviour of the gel. The phase behaviour of ternary systems (gelator + water + base) was studied by developing the corresponding ternary phase diagrams. From this study, the promising homogeneous viscous phases were converted into hard, irreversible gel beads by cross-linking the gelator with divalent cations Ca2+, Ba2+ and Sr2+. These gel beads were studied for base entrapment efficiency and leaching of the base. The GEBCs were used for the condensation of salicylaldehydes and methyl/ethyl acetoacetate to obtain 3-acetylcoumarins.