496-41-3Relevant articles and documents
Palladium-Catalyzed C?H Functionalization of Phenyl 2-Pyridylsulfonates
Li, Bin,Guo, Dong-Dong,Guo, Shi-Huan,Pan, Gao-Fei,Gao, Ya-Ru,Wang, Yong-Qiang
, p. 130 - 144 (2017)
An efficient palladium(II)-catalyzed intermolecular direct ortho-alkenylation and acetoxylation of phenols has been developed. The reaction proceeded via a seven-membered cyclopalladated intermediate and showed complete regio- and diastereoselectivity. The approach also provided an efficient route for the synthesis of coumarins and benzofurans.
1,4-Addition of an aryllithium reagent to diethyl ketomalonate. Scalable synthesis of ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate
Rocke, Benjamin N.,Conn, Edward L.,Eisenbeis, Shane A.,Ruggeri, Roger B.
, p. 5467 - 5470 (2012)
While optimizing the synthesis of pharmaceutical building block 3 [ethyl 1-(hydroxymethyl)-1,3-dihydroisobenzofuran-1-carboxylate], we encountered an unusual addition of an aryllithium reagent to the ketone oxygen atom of diethyl ketomalonate. Compound 3 was ultimately prepared on a large scale by a two-step sequence involving (1) annulation of a functionalized Grignard reagent with diethyl ketomalonate and (2) selective mono-reduction of a geminal diester using lithium tri-tert-butoxyaluminum hydride. 2012 Elsevier Ltd. All rights reserved.
Oxidative Cleavage of β -Keto Sulfones via Nitrous Acid
Abdel-Aziz, Hatem A.
, (2014)
The reaction of nitrous acid with 1-aryl-2-(arylsulfonyl)ethanones 3a-e afforded the unexpected arenecarboxylic acids 12a-e, formic acid 14, and benzene/4-toluenesulfinic acid 15a, b through oxidative cleavage reaction. 4-Chlorobenzoic acid (12a), [1,1′-biphenyl]-4-carboxylic acid (12b), 2-naphthoic acid (12c), 2-thiophenecarboxylic acid (12d), and 2-benzofurancarboxylic acid (12e) were isolated in 72%, 62%, 55%, 58%, and 62% yields, respectively. The reported mechanistic pathways proposed the production of 1-aryl-2-(phenyl/tolylsulfonyl)ethane-1,2-dione 7 instead of arenecarboxylic acids 12. A mechanistic pathway to explain the reaction of nitrous acid with 1-aryl-2-(arylsulfonyl)ethanones 3a-e was suggested. In this pathway, the intermediate 1,2-oxazete 10 lost benzene/4-toluenesulfinic acid 15 to produce 1,2-oxazet-3-one 11. Ring cleavage of the latter intermediate afforded the arenecarboxylic acids 12.
Synthesis and biological evaluation of a series of novel benzofuran-2-carboxylate 1,2,3-triazoles
Bhaskar, K.,Yadav, J. S.
, p. 767 - 774 (2021/09/28)
A facile and efficient synthetic route has been developed to substituted benzofuran-2-carboxylate 1,2,3-triazoles for the first time by reacting prop-2-yn-1-yl benzofuran-2-carboxylate with a variety of substituted aryl/benzyl azides in DMF/H2O system employing standard click reaction. This new method has the lead of good yields, inexpensive reagents, easily available, easy work-up, mild reaction conditions, and environmentally friendly reaction conditions. All these compounds have been characterized by modern spectral techniques such as IR, 1H NMR, and mass spectroscopy, etc. Evaluation of synthesized compounds for antimicrobial activity against specific bacterial strains like Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa along with antifungal activity against Aspergillus Niger and Sclerotium rolfsii have been carried out.
Investigation of the effect of different linker chemotypes on the inhibition of histone deacetylases (HDACs)
Linciano, Pasquale,Benedetti, Rosaria,Pinzi, Luca,Russo, Fabiana,Chianese, Ugo,Sorbi, Claudia,Altucci, Lucia,Rastelli, Giulio,Brasili, Livio,Franchini, Silvia
, (2020/11/24)
Histone Deacetylases (HDACs) are among the most attractive and interesting targets in anticancer drug discovery. The clinical relevance of HDAC inhibitors (HDACIs) is testified by four FDA-approved drugs for cancer treatment. However, one of the main drawbacks of these drugs resides in the lack of selectivity against the different HDAC isoforms, resulting in severe side effects. Thus, the identification of selective HDACIs represents an exciting challenge for medicinal chemists. HDACIs are composed of a cap group, a linker region, and a metal-binding group interacting with the catalytic zinc ion. While the cap group has been extensively investigated, less information is available about the effect of the linker on isoform selectivity. To this aim, in this work, we explored novel linker chemotypes to direct isoform selectivity. A small library of 25 hydroxamic acids with hitherto unexplored linker chemotypes was prepared. In vitro tests demonstrated that, depending on the linker type, some candidates selectively inhibit HDAC1 over HDAC6 isoform or vice versa. Docking calculations were performed to rationalize the effect of the novel linker chemotypes on biologic activity. Moreover, four compounds were able to increase the levels of acetylation of histone H3 or tubulin. These compounds were also assayed in breast cancer MCF7 cells to test their antiproliferative effect. Three compounds showed a significant reduction of cancer proliferation, representing valuable starting points for further optimization.
Synthesis and biological evaluation of novel shikonin-benzo[b]furan derivatives as tubulin polymerization inhibitors targeting the colchicine binding site
Kong, Ling-Yi,Leng, Jia-Fu,Lian, Bao-Ping,Shao, Yu-Ying,Xia, Yuan-Zheng,Yin, Yong
, (2020/02/11)
A novel series of shikonin-benzo[b]furan derivatives were designed and synthesized as tubulin polymerization inhibitors, and their biological activities were evaluated. Most compounds revealed the comparable anti-proliferation activities against the cancer cell lines to that of shikonin and simultaneously low cytotoxicity to non-cancer cells. Among them, compound 6c displayed powerful anti-cancer activity with the IC50 value of 0.18 μM against HT29 cells, which was significantly better than that of the reference drugs shikonin and CA-4. What's more, 6c could inhibit tubulin polymerization and compete with [3H] colchicine in binding to tubulin. Further biological studies depicted that 6c can induce cell apoptosis and cell mitochondria depolarize, regulate the expression of apoptosis related proteins in HT29 cells. Besides, 6c actuated the HT29 cell cycle arrest at G2/M phase, and influenced the expression of the cell-cycle related protein. Moreover, 6c displayed potent inhibition on cell migration and tube formation that contributes to the antiangiogenesis. These results prompt us to consider 6c as a potential tubulin polymerization inhibitor and is worthy for further study.
Tandem Synthesis of 2-Carboxybenzofurans via Sequential Cu-Catalyzed C-O Coupling and Mo(CO)6-Mediated Carbonylation Reactions
Mo, Qinliang,Sun, Nan,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
, p. 11490 - 11500 (2020/10/12)
A modular tandem synthesis of 2-carboxybenzofurans from 2-gem-dibromovinylphenols has been established based on a sequence of Cu-catalyzed intramolecular C-O coupling and Mo(CO)6-mediated intermolecular carbonylation reactions. This protocol allowed one-step access to a broad variety of functionalized benzofuran-2-carboxylic acids, esters, and amides in good to excellent yields under Pd- and CO gas-free conditions.
Synthesis and AChE inhibitory activity of N-glycosyl benzofuran derivatives
Cao, Zhi-Ling,Liu, Shu-Hao,Liu, Wei-Wei,Liu, Xiu-Jian,Ren, Shu-Ting,Shi, Da-Hua,Wang, Lei,Wang, You-Xian,Wu, Yu-Ran
, p. 162 - 166 (2020/01/28)
Six N-glycosyl benzofuran derivatives were synthesized by the catalysis of organic bases and condensation agents. The benzofuran derivatives were obtained by the reaction of various salicylaldehydes in acetone, and then hydrolyzed to the corresponding carboxylic acids. Finally, the target compounds were synthesized by acylation and the reaction conditions were optimized. The acetylcholinesterase (AChE) inhibitory activity of the desired compounds was tested using Ellman's method. Most of the compounds showed acetylcholinesterase-inhibition activity; N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carbxamide (5a) showed the best acetylcholinesterase inhibition, with an inhibitory rate of 84%.
A benzofuran -2 - preparation of formic acid method (by machine translation)
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Paragraph 0019-0048, (2019/01/24)
A benzofuran - 2 - carboxylic acid, which belongs to the benzofuran - 2 - carboxylic acid technical field. Is to metallic iron porphyrin catalytic oxygen oxidation 2 - methyl benzofuran preparation of benzofuran - 2 - carboxylic acid, which belongs to the field of organic synthesis and green chemistry. The method uses 2 - methyl benzofuran as raw materials, in order to ethanol or ethanol aqueous solution as the solvent, metal porphyrin four (O - chlorophenyl) iron porphyrin as catalyst, oxygen as the oxidizing agent, sodium hydroxide or potassium hydroxide is used as the cocatalyst, for 80 - 130 °C reaction under 1 - 4 hours, after the reactant is acidified, filtration, recrystallization to obtain product benzofuran - 2 - carboxylic acid. The method of the invention catalyst the amount of raw material weight 0.02 - 0.05%, less catalyst levels and without the need of separation, clean oxygen as the oxidizing agent, and the pressure is 0.5 - 2.0 mpa, solvent environment friendly, the reaction temperature is lower, the reaction raw materials through a simple separation, but also can be recycled. (by machine translation)
Amide pyridine derivative and application thereof
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Paragraph 0076; 0079; 0080, (2019/02/06)
The invention belongs to the technical field of medicine and relates to an amide pyridine derivative which is shown as a general formula I. The invention further relates to stereoisomer and pharmaceutically-acceptable salt, hydrate, solvate or prodrug of the amide pyridine derivative. The definitions of substituent groups of Ar, M, R and Py are given out in an instruction book. The invention further relates to a method for preparing the compound shown in the general formula I, pharmaceutical composition containing the compound and application of the compound and the pharmaceutical compositionin preparing medicine for treating and preventing superficial-layer fungal diseases and deep-layer fungal diseases.
