620-73-5Relevant academic research and scientific papers
Preparation method of benzofuran -2-(3H)- ketone (by machine translation)
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Paragraph 0021-0023; 0026-0028; 0031-0033; 0036-0038; 0041-, (2020/03/06)
The preparation method of the benzofuran, 2-(3H)- ketone takes the phenol, as the raw material, and the α - chloroacetyl chloride in the esterification reaction to react itself to form benzofuran - Friedel - Crafts, 2 (Benzofuran-2.(3H)-one. The method greatly shortens, the reaction conditions of the reaction path which is reported in, the art and the chloroacetyl chloride . The method does, not need to add, highly toxic compound sodium cyanide to form benzofuran-2-(-(H)-one in a, simple, and easily available raw. material. The invention greatly shortens the reaction cost and has high industrial application value in the synthesis step. (by machine translation)
Flavone inspired discovery of benzylidenebenzofuran-3(2H)-ones (aurones) as potent inhibitors of human protein kinase CK2
Bdzhola, V. G.,Bilokin, Y. V.,Borysenko, I. P.,Lukashov, S. S.,Protopopov, M. V.,Prykhod'ko, A. O.,Starosyla, S. A.,Vdovin, V. S.,Yarmoluk, S. M.
, (2020/07/21)
In this work, we describe the design, synthesis and SAR studies of 2-benzylidenebenzofuran-3-ones (aurones), a new family of potent inhibitors of CK2. A series of aurones have been synthesized. These compounds are structurally related to the synthetic flavones and showed nanomolar activities towards CK2. Biochemical tests revealed that 20 newly synthesized compounds inhibited CK2 with IC50 values in the nanomolar range. Further property-based optimization of aurones was performed, yielding a series of CK2 inhibitors with enhanced lipophilic efficiency. The most potent compound 12m (BFO13) has CLipE = 4.94 (CLogP = 3.5; IC50 = 3.6 nM) commensurable with the best known inhibitors of CK2.
Novel N-4-Piperazinyl Ciprofloxacin-Ester Hybrids: Synthesis, Biological Evaluation, and Molecular Docking Studies
Mahdavi, M.,Mostafavi, H.,Shahbazi, A.,Zarrini, G.
, p. 1558 - 1565 (2020/09/21)
Abstract: A series of novel N-4-piperazinylciprofloxacin-ester hybrids has been synthesized and the structures confirmed by1H and 13C NMR, FT-IRspectral data, and elemental analysis. The products have been tested in vitro for their antibacterial activity againstsix bacterial strains (MRSA, Staphylococcusepidermidis, Bacillussubtilis, Escherichia coli,Salmonella enterica, and Klebsiella pneumoniae) and have demonstrated goodantibacterial activity with MIC values range 6.25–200 μg/mL. Antifungal andcytotoxic activities of the products have been tested against Candida kefyr and human leukemia K562 cell line,respectively. All compounds inhibit growth of K562 cells more efficiently thanthe parent ciprofoxacin in a dose- and duration-dependent way. Molecular dockingstudies performed for the compound 3i indicatesthat similarly to ciprofloxacin it can act as an inhibitor of S. aureus DNA gyrase.
An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes
Khairnar, Pankaj V.,Lung, Tsai-Hui,Lin, Yi-Jung,Wu, Chi-Yi,Koppolu, Srinivasa Rao,Edukondalu, Athukuri,Karanam, Praneeth,Lin, Wenwei
supporting information, p. 4219 - 4223 (2019/06/17)
α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.
Substituted phenyl[(5-benzyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetates/acetamides as alkaline phosphatase inhibitors: Synthesis, computational studies, enzyme inhibitory kinetics and DNA binding studies
Iqbal,Ashraf,Hassan, Mubashir,Abbas,Jabeen, Erum
, (2019/07/09)
Substituted phenyl[(5-benzyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetates/acetamides 9a-j were synthesized as alkaline phosphatase inhibitors. Phenyl acetic acid 1 through a series of reactions was converted into 5-benzyl-1,3,4-oxadiazole-2-thione 4. The intermediate oxadiazole 4 was then reacted with chloroacetyl derivatives of phenols 6a-f and anilines derivatives 8a-d to afford the title oxadiazole derivatives 9a-j. All of the title compounds 9a-j were evaluated for their inhibitory activity against human alkaline phosphatise (ALP). It was found that compounds 9a-j exhibited good to excellent alkaline phosphatase inhibitory activity especially 9h displayed potent activity with IC50 value 0.420 ± 0.012 μM while IC50 value of standard (KH2PO4) was 2.80 μM. The enzyme inhibitory kinetics of most potent inhibitor 9h was determined by Line-weaever Burk plots showing non-competitive mode of binding with enzyme. Molecular docking studies were performed against alkaline phosphatase enzyme (1EW2) to check the binding affinity of the synthesized compounds 9a-j against target protein. The compound 9h exhibited excellent binding affinity having binding energy value (?7.90 kcal/mol) compared to other derivatives. The brine shrimp viability assay results proved that derivative 9h was non-toxic at concentration used for enzyme assay. The lead compound 9h showed LD50 106.71 μM while the standard potassium dichromate showed LD50 0.891 μM. The DNA binding interactions of the synthesized compound 9h was also determined experimentally by spectrophotometric and electrochemical methods. The compound 9h was found to bind with grooves of DNA as depicted by both UV–Vis spectroscopy and cyclic voltammetry with binding constant values 7.83 × 103 and 7.95 × 103 M?1 respectively revealing significant strength of 9h-DNA complex. As dry lab and wet lab results concise each other it was concluded that synthesized compounds, especially compound 9h may serve as lead compound to design most potent inhibitors of human ALP.
Design, synthesis, biological evaluation and molecular modeling study of new thieno[2,3-d]pyrimidines with anti-proliferative activity on pancreatic cancer cell lines
Salem, Mohamed S.H.,Abdel Aziz, Yasmine M.,Elgawish, Mohamed S.,Said, Mohamed M.,Abouzid, Khaled A.M.
, (2019/12/24)
Pancreatic cancer is one of the most challenging diseases with seven months only as median survival time due to its poor prognosis. Several enzymes are blamed for the progress of pancreatic cancer especially, platelet-derived growth factor receptors (PDGFRs), this in turn makes them promising targets for its treatment. In this study, twenty eight new compounds based on thieno[2,3-d]pyrimidine scaffold were synthesized as anti-pancreatic cancer agents mimicking the benzofuro[3,2-d]pyrimidine derivative, amuvatinib. Various linkers including amides, esters, ketones, urea and thiourea derivatives were utilized to study their effect on the anti-proliferative activity of these compounds. Most of the tested compounds revealed good cytotoxic activities against pancreatic carcinoma cell line PANC-1. Compound 9d showed the highest cytotoxicity with an IC50 value of 5.4 μM. Furthermore, 9d showed excellent platelet derived growth factor receptor (PDGFR-α) inhibitory activity, with IC50 value 0.155 μM. Docking study was carried out into PDGFR-α active site which showed comparable binding mode to that of FDA approved PDGFR-α inhibitor, imatinib. 3D-Quantitative structure activity relationship (QSAR) model was built up with five-featured pharmacophore which could be implemented for emerging effective lead structures. These compounds could serve as a new chemotype for discovering new agents for pancreatic cancer therapy.
Synthesis and antibacterial activity of 3-benzylamide derivatives as FtsZ inhibitors
Hu, Zhongping,Zhang, Shasha,Zhou, Weicheng,Ma, Xiang,Xiang, Guangya
supporting information, p. 1854 - 1858 (2017/04/04)
The emergence and spread of multidrug-resistant strains of the human pathological bacteria are generating a threat to public health worldwide. In the current study, a series of PC190723 derivatives was synthesized and investigated for their antimicrobial activity. The compounds exhibited good activity against several Gram-positive bacteria as determined by comparison of diameters of the zone of inhibition of test compounds and standard antibiotics. Compound 9 with a fluorine substitution on the phenyl ring showed the best antibacterial activity in the series against M. smegmatis with the zone ratio of 0.62, and against S. aureus with the zone ratio of 0.44. The results from this study indicate that based on the unique 3-methoxybenzamide pharmacophore, compound 9 may represent a promising lead candidate against Gram-positive bacteria that are worthy of further investigation
METHOD FOR PRODUCING CARBONATE COMPOUND AND METHOD FOR PRODUCING AROMATIC POLYCARBONATE
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Paragraph 0193-0195, (2015/06/10)
The present invention relates to a method for producing a carbonate compound containing: a first step of reacting a compound represented by the following Formula (1) with a compound represented by the following Formula (21) or a compound represented by the following Formula (22) to obtain a reaction mixture containing a carbonate compound, and a second step of bringing the reaction mixture containing a carbonate compound into contact with a strongly basic compound, in which R1 represents a monovalent organic group, and R2 represents a divalent organic group.
Synthesis of fused piperidinones through a radical-ionic cascade
Godineau, Edouard,Schenk, Kurt,Landais, Yannick
supporting information; experimental part, p. 6983 - 6993 (2009/05/09)
(Chemical Equation Presented) Azabicyclo[4.3.0]nonanes were assembled, from chiral allylsilanes possessing an oxime moiety, using a stereocontrolled formal [2 + 2 + 2] radical-ionic process. The cascade involves the addition of an α-iodoester to the less substituted end of the enoxime which is then followed by a 5-exo-trig cyclization onto the aldoxime function, producing an alkoxyaminyl radical species which finally lactamizes to afford the titled piperidinone. High levels of stereoinduction were observed, demonstrating the ability of a silicon group located at the allylic position to efficiently control the stereochemistry of the two newly created stereogenic centers. When the radical cascade was extended to ketoximes, the resulting sterically hindered alkoxyaminyl radical did not react further with the initiator Et3B to produce the expected nucleophilic amidoborane complex. In sharp contrast, this long-lived radical recombined with the initial α-stabilized ester radical to produce a cyclopentane incorporating two ester fragments.
Synthesis of substituted 3-arylpiperidines and 3-arylpyrrolidines by radical 1,4 and 1,2-aryl migrations
Gheorghe, Alexandru,Quiclet-Sire, Béatrice,Vila, Xavier,Zard, Samir Z.
, p. 7187 - 7212 (2008/02/07)
A route to 3-arylpiperidines and 3-arylpyrrolidines involving radical 1,4- and 1,2-aryl migrations has been explored. For the piperidines, the first route requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with lauroyl peroxide to give the corresponding 1,4-aryl transfer product. This compound can be converted into the desired piperidine derivative following acidic hydrolysis. For the second approach to piperidines, addition of an α-keto xanthate to olefins of type 14 causes 1,2-aryl migration leading to an α,β-unsaturated ester, which can be converted into a piperidine by the action of ammonia or a primary amine and sodium cyanoborohydride. Substituted 3-arylpyrrolidines can be obtained by simply starting with an α-amido substituted xanthate.
