38488-19-6Relevant academic research and scientific papers
Novel benzenesulfonamides aryl and arylsulfone conjugates adopting tail/dual tail approaches: Synthesis, carbonic anhydrase inhibitory activity and molecular modeling studies
Eldeeb, Assem H.,Abo-Ashour, Mahmoud F.,Angeli, Andrea,Bonardi, Alessandro,Lasheen, Deena S.,Elrazaz, Eman Z.,Nocentini, Alessio,Gratteri, Paola,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
supporting information, (2021/05/10)
New series of benzenesulfonamide and benzoic acid derivatives were designed and synthesized using tail/dual tail approach to improve potency and selectivity as carbonic anhydrase inhibitors. The synthesized compounds evaluated as CAIs against isoforms hCA I, II, IV and IX with acetazolamide (AAZ) as standard inhibitor. The benzenesulfonamide derivatives 7a-d, 8a-h, 12a-c, 13a and 15a-c showed moderate to potent inhibitory activity with selectivity toward isoform hCA II, especially, compound 13a with (Ki = 7.6 nM), while the benzoic acid analogues 12d-f, 13b and 15d-f didn't show any activity except compounds 12d,f and 15e that showed weak activity. Additionally, molecular docking was performed for compounds 7a, 8a, 8e, 12a, 13a and 15a on isoform hCA I, II to illustrate the possible interaction with the active site to justify the inhibitory activity.
Oxidative Sulfonylation of Hydrazones Enabled by Synergistic Copper/Silver Catalysis
Xu, Jun,Shen, Chao,Qin, Xian,Wu, Jie,Zhang, Pengfei,Liu, Xiaogang
, p. 3706 - 3720 (2021/02/05)
A copper/silver-cocatalyzed protocol for oxidative sulfonylation of hydrazones is demonstrated. A wide range of β-ketosulfones and N-acylsulfonamides are directly synthesized in moderate to good yields. Our work provides a viable method for scalable preparation of β-ketosulfone derivatives that have found wide applications in the pharmaceutical industry.
A glucose oxidase-hemoglobin system for efficient oxysulfonylation of alkenes/alkynes in water
Li, Chen,Li, Fengxi,Li, Zhengqiang,Liu, Jiaxu,Su, Jiali,Wang, Chunyu,Wang, Lei,Xu, Yaning,Yu, Yue
, (2020/12/29)
Background: β-ketosulfones are important bioactive compounds that have been extensively studied in organic chemistry. In this work, a green and efficient process for the synthesis of β-ketosulfones from alkenes (1) or alkynes (3) with sodium benzenesulfinate (2) was developed. Results: Under optimal conditions (alkenes (0.5 mmol) or alkynes (0.5 mmol), sodium benzenesulfinate (0.5 mmol), water (2 mL), hemoproteins (heme concentration: 0.06 mol%), GOX (42 U/ml), room temperature, 2 h), high yields of β-ketosulfones could be obtained when HgbRb (hemoglobin from rabbit blood) and GOX (glucose oxidase from Aspergillus niger) was used as the catalyst. Conclusion: This enzymatic method demonstrates the great potential for the synthesis of β-ketosulfones and extends the application of dual protein systems in organic synthesis.
A Compartmentalized-type Bifunctional Magnetic Catalyst for One-pot Aerobic Oxysulfonylation and Asymmetric Transfer Hydrogenation
Wang, Shitong,Wang, Chengyi,Lv, Ning,Tan, Chunxia,Cheng, Tanyu,Liu, Guohua
, p. 909 - 915 (2020/11/30)
Utilization of the confined cavity of the mesoporous silica, the exploration of the synergetic catalysis process for sequential organic transformations has great significance in asymmetric catalysis. In this study, the yolk-shell-structured magnetic nanoparticles with the chiral Ru/diamine species within the nanochannels of the outer mesoporous silica shell and the FeCl3 species on the inner magnet core are fabricated. The electron microscopy images and the structural characterizations disclose the uniformly distributed magnetic nanoparticles with the well-defined single-site ruthenium/diamine active centers onto the outer silica shell. As a yolk-shell-structured bifunctional magnet catalyst, the FeCl3 species enables an efficient aerobic oxysulfonylation between aryl-substituted terminal alkynes and sodium sulfinates to the β-keto sulfones intermediates, and the ruthenium/diamine species sequentially reduces the in-situ generated intermediate to the chiral β-hydroxysulfones products. As we envision, this one-pot aerobic oxysulfonylation/asymmetric transfer hydrogenation process affords various chiral β-hydroxysulfones in high yields with excellent enantioselectivities. Furthermore, this magnetic catalyst can also be conveniently recovered via an additional outer magnet and repeatedly recycled, showing a potential application in industrial interest.
Copper-catalyzed aerobic oxidative cross-coupling reactions of vinylarenes with sulfinate salts: A direct approach to β-ketosulfones
Chen, Yu,Xu, Lei,Wang, Biyu,Jiang, Jingjing,Sun, Yixiang,Li, Longchun
, (2021/01/25)
A copper-catalyzed aerobic oxidative cross-coupling reactions for the synthesis of β-ketosulfones via formation of a C[sbnd]S bond has been demonstrated. Promoted by the crucial copper catalyst, perfect selectivity and good to excellent yields could be achieved. This method, including inexpensive copper catalyst, wide functional group tolerance, and open air conditions, make it very attractive and practical. More importantly, it also provides a versatile tool for the construction of β-ketosulfones from basic starting materials under mild conditions.
Synthesis of β-ketosulfone derivatives as new non-cytotoxic urease inhibitors in vitro
Iqbal Choudhary, M.,Iqbal, Sarosh,Khan, Ajmal,Khan, Khalid Mohammed,Kiran, Shumaila,Nazir, Rashid,Perveen, Shahnaz
, p. 244 - 255 (2020/03/10)
Background: Peptic ulcer and urolithiasis are largely due to infection caused by urease-producing bacteria. Therefore, the discovery of urease inhibitors is an important area of medicinal chemistry research. Objective: The main aim of the work was to identify novel urease inhibitors with no cytotoxicity. Method: During the current study, a series of β-ketosulfones 1-26 was synthesized in two steps and evaluated for their in vitro urease inhibition potential. Results: Out of twenty-six compounds, seventeen have shown good to significant urease inhibitory activity with IC50 values ranging between 49.93-351.46 μM, in comparison to standard thiourea (IC50 = 21 ± 0.11 μM). Moreover, all compounds found to be non-cytotoxic against normal 3T3 cell line. Conclusion: This study has identified β-ketosulfones as novel and non-cytotoxic urease inhibitors.
One-pot synthesis of β-ketosulfones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water
Zhang, Yaohong,Luo, Mengqiang,Li, Yan,Shen, Runfu,Qi, Chenze,Wang, Hai,Cheng, Kai
supporting information, (2020/10/26)
A novel, facile and efficient strategy for the one-pot synthesis of β-ketosulfones from readily available sulfonyl chloride, hydrazine hydrate and vinyl azides is described. The reaction proceeded very smoothly affording diverse β-ketosulfones in moderate to good yields. This new procedure has the advantages of environmental benign, easy and simple operation, low cost and wide tolerance of functional groups, which provides a highly fascinating protocol to access β-ketosulfones.
Photo-Mediated Decarboxylative Ketonization of Atropic Acids with Sulfonyl Hydrazides: Direct Access to β-Ketosulfones
Chen, Jie,Allyson, Zoe G.,Xin, Jing-Rui,Guan, Zhi,He, Yan-Hong
supporting information, p. 2045 - 2051 (2020/02/11)
An efficient formation of synthetically and biologically relevant β-ketosulfones via a photo-mediated decarboxylative ketonization of atropic acids was disclosed. The approach features metal-free conditions, good functional group compatibility, readily available starting materials and the use of ubiquitous dioxygen as both oxygen source and oxidant. Furthermore, mechanistic studies reveal that the decarboxylative ketonization reaction proceeds via a radical mechanism and may involve a radical chain reaction. (Figure presented.).
Method for preparing β-ketone sulfone compound through visible light-mediated atorvastatin decarboxylation reaction (by machine translation)
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Paragraph 0134-0139, (2020/04/29)
The preparation method of the invention has the characteristics β - that raw materials are simple and easy to obtain, the operation is simple . the reaction conditions are mild, and the reaction system is not sensitive to water . is a method for preparing,ketone sulfone compounds, by using environment-friendly (-source extensive atorvastatin as reactants), and then fully dissolving β -communicating oxygen balloon, in a mixed solvent of acetonitrile and water to obtain, ketal sulphone compounds by reacting, with a stable odorless sulfonyl hydrazide in a mixed solvent of acetonitrile and water under the irradiation of visible light. (by machine translation)
Beta-keto sulfone derivatives as well as preparation method and application thereof
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Paragraph 0041; 0042; 0055-0058; 0078; 0079, (2020/01/03)
The invention discloses beta-keto sulfone derivatives as well as a preparation method and application thereof. The preparation method includes the following step: performing a reaction by using olefinazide and sulfonyl hydrazide as starting material, CuSO.5HO as a catalyst and water as a reaction solvent at 90 DEG C for 2-4 h. According to the method provided by the invention, the catalystCuSO.5HO is used in the reaction system, so that the reaction is effectively promoted, a self-coupling reaction of the sulfonyl hydrazide is inhibited, and the yield of the reaction is improved;meanwhile, the reaction reagents and catalyst used in the method are stable, cheap and easy to obtain, mass production is facilitated, and a novel effective way is provided for construction of the structures; the reaction solvent is water, and has the advantages of green economy and environmental protection; and in addition, results of activity experiments show that the product can inhibit 11 beta-hydroxysteroid dehydrogenase to a certain extent, so that the preparation method and the product have important application significance in the field of medicine.
