- Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts
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We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.
- Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng
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p. 8338 - 8342
(2021/10/25)
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- Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis
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An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.
- Cui, Wenwen,Jiang, Min,Lv, Jian,Song, Xiuyan,Sun, Kai,Xu, Guiyun,Yan, Qiuli,Yang, Daoshan
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supporting information
p. 3663 - 3668
(2021/05/31)
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- Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates
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A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive.
- Mulina, Olga M.,Ilovaisky, Alexey I.,Opatz, Till,Terent'ev, Alexander O.
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supporting information
(2021/01/11)
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- Visible-light-promotedE-selective synthesis of α-fluoro-β-arylalkenyl sulfidesviathe deoxygenation/isomerization process
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Regioselective synthesis of α-fluoro-β-arylalkenyl sulfides has been established withgem-difluoroalkenes and sodium sulfinates in a transition-metal-free manner. A series of control experiments were executed to demonstrate thiol radicals and anions as the proposed intermediates. Notably, regioselectiveZ→Eisomerization was achieved under green light irradiation in the absence of a photoinitiator.
- Li, Yuxiu,Li, Xiangqian,Li, Xiaowei,Shi, Dayong
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supporting information
p. 2152 - 2155
(2021/03/06)
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- Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol
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Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.
- Chen, Yi-Xuan,Wang, Zhu-Jun,Xiao, Jun-An,Chen, Kai,Xiang, Hao-Yue,Yang, Hua
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supporting information
p. 6558 - 6562
(2021/08/23)
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- A three-component reaction of arynes, sodium sulfinates, and aldehydes toward 2-sulfonyl benzyl alcohol derivatives
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A novel three-component reaction of arynes, sodium sulfinates, and aldehydes under mild reaction conditions is described. This transformation provides a direct synthetic approach to 2-sulfonyl benzyl alcohol derivatives, which could be rapidly converted to diverse arylsulfur compounds via the transformation of the corresponding hydroxyl groups. Various aryne precursors, sodium arenesulfinates, and aromatic aldehydes can be effectively converted to the desired products in 40-84% yields (29 examples).
- Chen, Qian,Gao, Yang,Hu, Yifan,Huang, Yuanting,Li, Xianwei,Zhao, Xi
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p. 7066 - 7073
(2021/08/25)
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- Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy
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DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, the success in DEL technology stems from the molecular diversity of the chemical libraries. However, the construction of DELs has been restricted by the idiosyncratic needs and the required low concentration (~1 mM or less) of the library intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor-acceptor (EDA) complex and a reversible adsorption to solid support (RASS) strategy. This protocol provides a unique solution to the challenges of increasing the reactivity of highly diluted DNA substrates and reducing the residues of heavy metals from photocatalysts. A series of on-DNA indole sulfone and selenide derivatives were obtained with good to quantitative conversions. It is anticipated that these mild-condition on-DNA radical reactions will significantly improve the chemical diversity of DELs and find widespread utility to DEL construction.
- Lin, Bizhen,Lu, Weiwei,Chen, Zhen-Yu,Zhang, Yue,Duan, Yin-Zhe,Lu, Xiaojie,Yan, Ming,Zhang, Xue-Jing
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supporting information
p. 7381 - 7385
(2021/10/12)
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- Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates
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This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.
- Cheng, Lan,Guo, Jianbo,Li, Yufei,Liang, Xin,Wang, Qingmin,Xia, Qing,Zhang, Pei,Zhang, Weihua
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supporting information
p. 8865 - 8870
(2021/11/30)
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- Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron
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The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.
- Qiu, Di,Li, Songyi,Yue, Guanglu,Mao, Jinshan,Xu, Bei,Yuan, Xinyu,Ye, Fei
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supporting information
(2021/11/04)
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- Copper catalysed oxidative α-sulfonylation of branched aldehydes using the acid enhanced reactivity of manganese(iv) oxide
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The oxidative coupling of secondary aldehydes and sulfinate salts is achieved using copper catalysis to form α-sulfonyl aldehydes. The use of an acidic co-solvent is important to adjust the oxidation potential of MnO2 as an oxidant. A broad range of sulfonylated aldehydes is prepared, and their further functionalisation is demonstrated. A dual ionic/radical pathway mechanism is proposed.
- Higham, Joe I.,Bull, James A.
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supporting information
p. 4587 - 4590
(2020/05/05)
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- Cross coupling of sulfonyl radicals with silver-based carbenes: A simple approach to β-carbonyl arylsulfones
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A coupling reaction between sulfonyl radicals and silver-based carbenes has been well established. This simple radical-carbene coupling (RCC) process provided an efficient approach to a variety of β-carbonyl arylsulfones from sodium arylsulfinates and diazo compounds, and was characterized by wide substrate scope, easy scale-up, simple manipulation, accessible starting materials, and mild reaction conditions.
- Li, Jingjing,Lian, Pengcheng,Wan, Xiaobing,Wang, Hanghang,Zheng, Yonggao
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supporting information
p. 2163 - 2169
(2020/03/27)
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- Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives
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A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.
- Wang, Fei,Liu, Bo-Xi,Rao, Weidong,Wang, Shun-Yi
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supporting information
p. 6600 - 6604
(2020/09/02)
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- Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants
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Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.
- Mulina, Olga M.,Pirgach, Dmitry A.,Nikishin, Gennady I.,Terent'ev, Alexander O.
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supporting information
p. 4179 - 4188
(2019/05/08)
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- Hydrosulfonylation of Unactivated Alkenes by Visible Light Photoredox Catalysis
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The anti-Markovnikov hydrosulfonylation of unactivated alkenes with sodium sulfinates was realized via [Ir(dF(CF3)ppy)2(dtbbpy)]PF6-mediated visible light photoredox catalysis. The presence of an acid such as acetic acid is essential for the reaction to take place. A variety of unactivated alkenes can be transformed into sulfones with good yield and high regioselectivity using this reaction, which is proposed to proceed by a radical mechanism.
- Wang, Juan-Juan,Yu, Wei
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supporting information
p. 9236 - 9240
(2019/11/19)
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- Copper-Catalyzed Enantioselective Construction of Tertiary Propargylic Sulfones
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Tertiary propargylic sulfones are of significant importance in organic synthesis and medicinal chemistry, but to date no general asymmetric synthesis approach has been developed. We disclose a versatile copper-catalyzed sulfonylation of propargylic cyclic carbonates using sodium sulfinates that allows the construction of propargylic sulfones featuring elusive quaternary stereocenters. This method provides the first successful example of such an enantioselective propargylic sulfonylation, features high asymmetric induction, wide functional group tolerance, and scalability, and enables attractive product diversification.
- Gómez, José Enrique,Cristòfol, àlex,Kleij, Arjan W.
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supporting information
p. 3903 - 3907
(2019/02/24)
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- Pd(II)-Catalyzed Direct Sulfonylation of Benzylamines Using Sodium Sulfinates
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A Pd(II)-catalyzed direct sulfonylation of benzylamines with sodium sulfinates using a removable bidentate directing group is illustrated. The transformation is highly regioselective and tolerates wide functional groups. The mechanistic study reveals that radical species are involved in this reaction. This method delivers a direct synthetic strategy to obtain highly functionalized sulfonylated benzylamines.
- Karmakar, Ujjwal,Samanta, Rajarshi
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p. 2850 - 2861
(2019/03/29)
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- Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates
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A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.
- Liu, Saiwen,Chen, Ru,Zhang, Jin
-
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- Switchable regioselection of C-H thiolation of indoles using different TMS counterions
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A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.
- Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
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p. 11864 - 11867
(2019/10/11)
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- Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates
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Copper-catalyzed difunctionalization of 2-vinylbenzoic acids with sodium sulfinates to construct substituted lactones has been realized. This protocol employs inexpensive CuCl2 as the catalyst, di-tert-butyl peroxide or O2 as the terminal oxidant, and readily available sodium sulfinates as sulfonylation reagents. High functional group tolerance and excellent yields were demonstrated by the efficient preparation of a wide range of γ-sulfonylated phthalides.
- Xiong, Yan-Shi,Zhang, Bin,Yu, Yang,Weng, Jiang,Lu, Gui
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p. 13465 - 13472
(2019/10/16)
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- Convenient method for preparation of aryl sulfinates from arenes and DABSO as the SO2 surrogates
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A safe and efficient protocol for the synthesis of aryl sulfinates from arenes and 1,4-diazabicyclo[2,2,2]octane bis(sulfur dioxide) (DABSO) under mild conditions is described. Through in situ infrared spectroscopic studies, a plausible mechanism for the sulfination reaction is proposed as well.
- Wang, Tianlei,Wang, Fumin,Shen, Jinghua,Pang, Tianting,Ren, Yanfei,Wu, Botao,Zhang, Xubin
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p. 1183 - 1187
(2018/02/26)
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- Preparation method of aromatic sulfinic acid compound
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The invention relates to a preparation method of an aromatic sulfinic acid compound. The preparation method includes the steps of: with Lewis acid as a catalyst, performing a Friedel-Crafts acylation reaction to an aromatic compound as a raw material with 1,4-diazabicyclo[2.2.2]octane (DABSO) in a solvent to generate a corresponding aromatic sulfinic acid compound. Compared with industrial preparation methods for the aromatic sulfinic acid compound in the prior art, the method can synthesize the aromatic sulfinic acid compound in one step, so that experiment operations are simplified and a high-polluting chlorosulfonation step is avoided. The method has mild reaction conditions, wherein the reaction can be carried out under a common normal temperature condition, so that a large amount of energy consumption in production is reduced. The DABSO, compared with gas-phase SO2, is convenient to store and transport, has stable properties at normal temperature and under normal pressure and has safe and simple operations. The raw materials are low in cost and easy to obtain, thus reducing production cost. The method has huge potential in practical use.
- -
-
Paragraph 0042; 0043; 0044; 0045; 0046
(2017/09/26)
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- Iodine/TBHP-Promoted One-Pot Deoxygenation and Direct 2-Sulfonylation of Quinoline N-Oxides with Sodium Sulfinates: Facile and Regioselective Synthesis of 2-Sulfonylquinolines
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A highly efficient iodine/TBHP-mediated one-pot deoxygenative and regioselective 2-sulfonylation of quinoline N-oxides with sodium sulfinate salts has been developed. This metal-, base-, and phosphorus-free protocol employs readily accessible and easy-to-handle reagents and can be conveniently carried out at room temperature under mild conditions, providing an alternative access to a series of 2-sulfonylquinolines and other related heteroaryl sulfone products in moderate-to-excellent yields within a short reaction time.
- Sumunnee, Ladawan,Buathongjan, Chonchanok,Pimpasri, Chaleena,Yotphan, Sirilata
-
supporting information
p. 1025 - 1032
(2017/02/15)
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- Iron(III) Chloride-Mediated Regio- and Stereoselective Chlorosulfonylation of Alkynes and Alkenes with Sodium Sulfinates
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The atom-economic and one-pot regio- and stereoselective addition of sodium arenesulfinates to either alkynes or alkenes can be achieved with an iron(III) chloride hexahydrate [FeCl3?6 H2O] catalytic system to afford β-haloalkenyl and β-chloroalkyl sulfones in moderate to good yields. (Figure presented.).
- Zeng, Kui,Chen, Lang,Chen, Yi,Liu, Yongping,Zhou, Yongbo,Au, Chak-Tong,Yin, Shuang-Feng
-
supporting information
p. 841 - 847
(2017/03/11)
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- Generation of trifluoromethyl thiolsulphonate through one-pot reaction of sulfonyl chloride and trifluoromethanesulfanylamides
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A novel and efficient tandem reaction of sulfonyl chloride and trifluoromethylsulfanylamide is described here for the synthesis of various trifluoromethyl thiolsulphonates with a broad functional group tolerance. In the process, it is believed that sulfinate generated from sulfonyl chloride is a critical intermediate and the additive 4-methylbenzenesulfonic acid (p-TsOH) facilitates the formation of “CF3S+”. Electrophilic trifluoromethylthiolation of in situ generated sulfinate and “CF3S+” provides the final products.
- Li, Yuewen,Qiu, Guanyinsheng,Wang, Hailong,Sheng, Jie
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supporting information
p. 690 - 693
(2017/01/28)
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- Iron-catalyzed synthesis of arylsulfinates through radical coupling reaction
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A novel strategy for installation of a sulfonyl fragment into arenes has been accomplished via an iron-catalyzed radical coupling reaction. Arene radicals derived from diaryliodoniums via single electron transfer reaction combine with sulfoxylate anion radicals readily generated from commercially available rongalite (HOCH2SO2Na·2H2O) to afford arylsulfinates efficiently at room temperature. In this protocol, a broad range of functional groups are tolerated to give products in good yields.
- Zhang, Weixi,Luo, Meiming
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p. 2980 - 2983
(2016/02/19)
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- Method for preparing aryl sulfinate
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The invention provides a method for preparing an aryl sulfinate compound through the reaction of diaryl iodonium salt and sodium formaldehyde sulfoxylate.At room temperature, the diaryl iodonium salt reacts with the sodium formaldehyde sulfoxylate for 10-120 minutes to generate the corresponding aryl sulfinate compound.The method has the advantages that the reaction conditions are mild, the used reagents re easy to obtain, the application range of a substrate is wide, operation is simple, reaction is quick, and the like.
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Paragraph 0016
(2016/10/08)
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- Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate
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An unexpected Cu-catalyzed deoxygenative C2-sulfonylation reaction of quinoline N-oxides in the presence of radical initiator K2S2O8 was developed that used sodium sulfinate as a sulfonyl coupling partner. The mechanism studies indicate that the reaction proceeds via Minisci-like radical coupling step to give sulfonylated quinoline with good chemical yields.
- Du, Bingnan,Qian, Ping,Wang, Yang,Mei, Haibo,Han, Jianlin,Pan, Yi
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supporting information
p. 4144 - 4147
(2016/08/30)
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- Sulfination of alcohols with sodium sulfinates promoted by BF3·OEt2: An unexpected access
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A BF3·OEt2-promoted direct substitution of various alcohols with sodium sulfinates affording sulfinates under mild conditions has been developed. Further reaction of the hydroxysteroids achieves the highly complex sulfinates in good yields, which are two potential pharmacophores routinely encountered in drug discovery.
- Huang, Mingming,Hu, Liangzhen,Shen, Hang,Liu, Qing,Hussain, Muhammad Ijaz,Pan, Jing,Xiong, Yan
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supporting information
p. 1874 - 1879
(2016/04/19)
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- Copper-Mediated 1,2-Difunctionalization of Styrenes with Sodium Arylsulfinates and tert-Butyl Nitrite: Facile Access to α-Sulfonylethanone Oximes
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A new copper-mediated synthesis of α-sulfonylethanone oximes from styrenes, sodium arylsulfinates and tert-butyl nitrite (t-BuONO; TBN) is presented. This intermolecular three-component method enables the one-step formation of C N and C S bonds under mild conditions, and represents a new, straightforward approach to α-sulfonylethanone oximes. (Figure presented.) .
- Yang, Ji,Liu, Yan-Yun,Song, Ren-Jie,Peng, Zhi-Hong,Li, Jin-Heng
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supporting information
p. 2286 - 2292
(2016/07/28)
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- Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature
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A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is
- Yang, Kai,Ke, Miaolin,Lin, Yuanguang,Song, Qiuling
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supporting information
p. 1395 - 1399
(2015/03/18)
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- Copper-mediated ortho C-H sulfonylation of benzoic acid derivatives with sodium sulfinates
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Copper-mediated direct ortho C-H bond sulfonylation of benzoic acid derivatives with sodium sulfinates was achieved by employing an 8-aminoquinoline moiety as the bidentate directing group. Various aryl sulfones were synthesized in good yields with excellent regioselectivity. This journal is
- Liu, Jidan,Yu, Lin,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Wang, Wenduo,Tan, Ze
-
supporting information
p. 6418 - 6421
(2015/04/14)
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- Visible Light-Mediated Metal-Free Synthesis of Vinyl Sulfones from Aryl Sulfinates
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Visible light and eosin Y catalyze the synthesis of vinyl sulfones from aryl sulfinates and alkenes by a photoredox process. The reaction scope is broad in aryl sulfinates and alkenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable vinyl sulfones.
- Meyer, Andreas Uwe,J?ger, Stefanie,Prasad Hari, Durga,K?nig, Burkhard
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supporting information
p. 2050 - 2054
(2015/06/23)
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- Synthesis of oxindoles through silver-catalyzed trifluoromethylation-, difluoromethylation- and arylsulfonylation-cyclization reaction of N-arylacrylamides
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Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced. Copyright
- Liu, Jidan,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Yang, Zhiyong,Tan, Ze
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supporting information
p. 3196 - 3202
(2014/06/09)
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- First palladium-catalyzed denitrated coupling of nitroarenes with sulfinates
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The first example of palladium-catalyzed protocol for the denitrated coupling of nitroarenes with sulfinates was developed, achieving aryl and heterocyclic sulfones in moderate to excellent yields. The cyclopalladated ferrocenylimine (I) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol %). The efficiency of this reaction was demonstrated by compatibility with a wide range of groups. Thus, the method represents a simple and facile procedure to access aryl and heterocyclic sulfones.
- Tian, Heng,Cao, Aijuan,Qiao, Lijun,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie
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supporting information
p. 9107 - 9112
(2015/03/05)
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- Synthesis and promising in Vitro antiproliferative activity of sulfones of a 5-nitrothiazole series
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The synthesis in water of new sulfone derivatives under microwave irradiation is described. This eco-friendly process leads to the expected products in good yields by reaction of various substituted sulfinates (commercially available or obtained by reduction of the corresponding sulfonyl chlorides) with 4-chloromethyl-2-methyl-5-nitro-1,3- thiazole. In order to evaluate the antiproliferative effect of these compounds, several sulfone derivatives are also dichlorinated on the Ca next to the sulfonyl group. An evaluation on different cancer cell lines reveals promising selective in vitro antiproliferative activity toward HepG2 human cell lines by dihydrogenated sulfones, suggesting further research should be to explore their anticancer potential in the treatment of liver cancer.
- Cohen, Anita,Crozet, Maxime D.,Rathelot, Pascal,Azas, Nadine,Vanelle, Patrice
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- Discovery of a novel class of orally active trypanocidal N-Myristoyltransferase inhibitors
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N-Myristoyltransferase (NMT) represents a promising drug target for human African trypanosomiasis (HAT), which is caused by the parasitic protozoa Trypanosoma brucei. We report the optimization of a high throughput screening hit (1) to give a lead molecule DDD85646 (63), which has potent activity against the enzyme (IC50 = 2 nM) and T. brucei (EC50 = 2 nM) in culture. The compound has good oral pharmacokinetics and cures rodent models of peripheral HAT infection. This compound provides an excellent tool for validation of T. brucei NMT as a drug target for HAT as well as a valuable lead for further optimization.
- Brand, Stephen,Cleghorn, Laura A. T.,McElroy, Stuart P.,Robinson, David A.,Smith, Victoria C.,Hallyburton, Irene,Harrison, Justin R.,Norcross, Neil R.,Spinks, Daniel,Bayliss, Tracy,Norval, Suzanne,Stojanovski, Laste,Torrie, Leah S.,Frearson, Julie A.,Brenk, Ruth,Fairlamb, Alan H.,Ferguson, Michael A. J.,Read, Kevin D.,Wyatt, Paul G.,Gilbert, Ian H.
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supporting information; experimental part
p. 140 - 152
(2012/03/09)
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