27918-36-1Relevant articles and documents
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.
Efficient synthesis of chiral β-hydroxy sulfones: Via iridium-catalyzed hydrogenation
Tao, Lin,Yin, Congcong,Dong, Xiu-Qin,Zhang, Xumu
supporting information, p. 785 - 788 (2019/01/30)
A highly efficient Ir/f-Amphol-catalyzed asymmetric hydrogenation of prochiral β-keto sulfones was successfully developed to prepare a series of chiral β-hydroxy sulfones with good to excellent results (62%->99% conversions, 35%-99% yields and 86%->99% ee). Our Ir/f-Amphol L4 catalytic system exhibited very high activity; the gram-scale asymmetric hydrogenation was performed well with just 0.005 mol% catalyst loading (S/C = 20,000) to afford the desired product 2a with >99% conversion, 99% yield and 93% ee.
Facile Synthesis of β-Keto Sulfones Employing Fenton's Reagent in DMSO
Chalikidi, Petrakis N.,Uchuskin, Maxim G.,Trushkov, Igor V.,Abaev, Vladimir T.,Serdyuk, Olga V.
supporting information, p. 571 - 575 (2018/01/11)
A new facile method for the synthesis of β-keto sulfones employing xanthates, DMSO, and Fenton's reagent is described. The reaction proceeds under very mild conditions providing a cost-effective straightforward approach to various β-keto sulfones in high yields.
Nickel-Catalyzed Highly Enantioselective Hydrogenation of β-Acetylamino Vinylsulfones: Access to Chiral β-Amido Sulfones
Long, Jiao,Gao, Wenchao,Guan, Yuqing,Lv, Hui,Zhang, Xumu
supporting information, p. 5914 - 5917 (2018/09/25)
The nickel/(S)-Binapine complex was found to be an efficient catalyst for asymmetric hydrogenation of β-acetylamino vinylsulfones to afford chiral β-Amido sulfones with excellent yields and enantioselectivities (up to 95% yields and >99% ee). This protocol has good compatibility with a series of substituted (Z)-β-acetylamino vinylsulfones or Z/E isomeric mixtures. A gram-scale reaction has also been achieved in the presence of a 0.2 mol % catalyst loading.
CO/O2 assisted oxidative carbon-carbon and carbon-heteroatom bond cleavage for the synthesis of oxosulfonates from DMSO and olefins
Shao, Ailong,Gao, Meng,Chen, Songtao,Wang, Tao,Lei, Aiwen
, p. 2175 - 2178 (2017/03/09)
Selective carbon-carbon and carbon-heteroatom bond cleavage was achieved in a one reaction system. With this strategy a novel Pd/Cu-catalyzed aerobic oxidative oxosulfonation of olefins with DMSO has been developed. Preliminary mechanistic investigations indicated that CO/O2 assisted the bond cleavage and the leaving groups from the starting materials were trapped by O2 and underwent a hydroxylation process.
Iron(III)-catalyzed aerobic oxidation and cleavage/formation of a C-S bond
Shi, Xiaokang,Ren, Xiaoyu,Ren, Zhiyong,Li, Jian,Wang, Yuling,Yang, Sizhuo,Gu, Jixiang,Gao, Qiang,Huang, Guosheng
supporting information, p. 5083 - 5088 (2014/08/18)
A new iron(III)-catalyzed synthesis of β-oxo sulfones is described that employs vinylarenes and readily available dimethyl sulfoxide (DMSO) with hydrazine and oxygen as the oxidant. The reaction tolerates various functional group substituents on the vinylarene substrates to afford β-oxo sulfones in moderate to good yields. The cleavage and formation of the C-S bond are the key steps of this transformation.
Catalytic and direct methyl sulfonylation of alkenes and alkynes using a methyl sulfonyl radical generated from a DMSO, dioxygen and copper system
Jiang, Yaojia,Loh, Teck-Peng
, p. 4939 - 4943 (2015/01/09)
This paper describes an efficient method to β-keto methyl sulfones and (E)-vinyl methyl sulfones using DMSO as the substrate. The methyl sulfonyl radical generated from DMSO in the presence of catalytic Cu(i) under O2 atmosphere is believed to be involved in this reaction. Isotopic labeling and 18O2 experiments were performed to investigate the reaction mechanism.
A new application of hypervalent iodine (λ5) reagents with organosulfonic acids for direct α-organosulfonyloxylation carbonyl compounds
Mahajan, Ulhas S.,Akamanchi, Krishnacharya G.
experimental part, p. 987 - 990 (2009/04/04)
Hypervalent iodine (λ5) reagents in combination with p-toluenesulfonic acid when reacted with ketones under reflux temperature in acetonitrile gave α-tosyloxy ketones in moderate to excellent yields. The reaction was developed further for both
Reactions of sulfonyl chlorides with silyl enol ethers catalysed by a ruthenium(II) phosphine complex: Convenient synthesis of β-keto sulfones
Kamigata, Nobumasa,Udodaira, Kumiko,Shimizu, Toshio
, p. 783 - 786 (2007/10/03)
The reactions of alkane- and arene-sulfonyl chlorides with silyl enol ethers in the presence of a ruthenium(II) phosphine complex are found to give β-keto sulfones in good to high yields.
