7605-28-9Relevant articles and documents
A Concise Route to 2-Sulfonylacetonitriles from Sodium Metabisulfite
Yao, Yanfang,Yin, Ziqing,Chen, Weiyun,Xie, Wenlin,He, Fu-Sheng,Wu, Jie
supporting information, p. 570 - 574 (2020/12/09)
A three-component reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and 3-azido-2-methylbut-3-en-2-ol under mild conditions is described. By using abundant and cheap sodium metabisulfite as the sulfur dioxide surrogate, this protocol features good functional group compatibility, affording 2-arylsulfonylacetonitriles in moderate to good yields. The reaction proceeds smoothly at room temperature without the need of any catalysts or additives. Moreover, the synthetic utility of this method is demonstrated by the transformation of 2-arylsulfonylacetonitrile into 2-arylsulfonyl acetamide and 2-arylsulfonylethylamine. (Figure presented.).
Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation
Zhou, Kaida,Liu, Jin-Biao,Xie, Wenlin,Ye, Shengqing,Wu, Jie
supporting information, p. 2554 - 2557 (2020/03/10)
Metal-free insertion of sulfur dioxide with aryl iodides and 3-azido-2-methylbut-3-en-2-ol under ultraviolet irradiation at room temperature is achieved, giving rise to 2-(arylsulfonyl)acetonitriles in moderate to good yields. Alkyl iodide is also workable under these conditions. This transformation proceeds smoothly under mild conditions with a broad substrate scope. Various functional groups are compatible including amino, ester, halo, and trifluoromethyl groups. No metal catalyst or additive is needed during the reaction process. Mechanistic studies show that under ultraviolet irradiation, an aryl radical is generated in situ from aryl iodide, which undergoes subsequent sulfonylation via the insertion of sulfur dioxide leading to arylsulfonyl radical intermediates. Then the arylsulfonyl radical reacts with 3-azido-2-methylbut-3-en-2-ol giving rise to the corresponding 2-(arylsulfonyl)acetonitrile.
Inhibitors of the Diadenosine Tetraphosphate Phosphorylase Rv2613c of Mycobacterium tuberculosis
G?tz, Kathrin H.,Hacker, Stephan M.,Mayer, Daniel,Dürig, Jan-Niklas,Stenger, Steffen,Marx, Andreas
, p. 2682 - 2689 (2017/10/27)
The intracellular concentration of diadenosine tetraphospate (Ap4A) increases upon exposure to stress conditions. Despite being discovered over 50 years ago, the cellular functions of Ap4A are still enigmatic. If and how the varied Ap4A is a signal and involved in the signaling pathways leading to an appropriate cellular response remain to be discovered. Because the turnover of Ap4A by Ap4A cleaving enzymes is rapid, small molecule inhibitors for these enzymes would provide tools for the more detailed study of the role of Ap4A. Here, we describe the development of a high-throughput screening assay based on a fluorogenic Ap4A substrate for the identification and optimization of small molecule inhibitors for Ap4A cleaving enzymes. As proof-of-concept we screened a library of over 42, 000 compounds toward their inhibitory activity against the Ap4A phosphorylase (Rv2613c) of Mycobacterium tuberculosis (Mtb). A sulfanylacrylonitril derivative with an IC50 of 260 ± 50 nM in vitro was identified. Multiple derivatives were synthesized to further optimize their properties with respect to their in vitro IC50 values and their cytotoxicity against human cells (HeLa). In addition, we selected two hits to study their antimycobacterial activity against virulent Mtb to show that they might be candidates for further development of antimycobacterial agents against multidrug-resistant Mtb.
Reactivity, Selectivity, and Stability in Sulfenic Acid Detection: A Comparative Study of Nucleophilic and Electrophilic Probes
Gupta, Vinayak,Paritala, Hanumantharao,Carroll, Kate S.
, p. 1411 - 1418 (2016/06/09)
The comparative reaction efficiencies of currently used nucleophilic and electrophilic probes toward cysteine sulfenic acid have been thoroughly evaluated in two different settings-(i) a small molecule dipeptide based model and (ii) a recombinant protein model. We further evaluated the stability of corresponding thioether and sulfoxide adducts under reducing conditions which are commonly encountered during proteomic protocols and in cell analysis. Powered by the development of new cyclic and linear C-nucleophiles, the unsurpassed efficiency in the capture of sulfenic acid under competitive conditions is achieved and thus holds great promise as highly potent tools for activity-based sulfenome profiling.
A molybdenum based metallomicellar catalyst for controlled and selective sulfoxidation reactions in aqueous medium
Chakravarthy, Rajan Deepan,Ramkumar, Venkatachalam,Chand, Dillip Kumar
, p. 2190 - 2196 (2014/04/17)
A surfactant based molybdenum system that exhibits catalytic activity for sulfoxidation reactions of various organic sulfides in aqueous medium has been developed and comprehensively characterized using IR, XRD, NMR, ESI-MS, DLS and TEM. The catalyst showcases remarkable selectivity for the preparation of both sulfoxides and sulfones in the range of good to excellent yields. Furthermore, the catalyst showed a high degree of tolerance towards various sensitive functional groups such as hydroxyl, acetal, aldehyde, amine, imine, oxime, cyano and alkene. the Partner Organisations 2014.
Ionic liquid catalyzed one-pot synthesis of novel spiro-2-amino-3- phenylsulfonyl-4H-pyran derivatives
Jin, Shuai-Shuai,Wang, Hong,Guo, Hong-Yun
, p. 2353 - 2356 (2013/06/26)
A series of novel spiro-2-amino-3-phenylsulfonyl-4H-pyran derivatives were synthesized via the three component, one pot reaction of phenylsulfonylacetonitrile and 1,3-dicarbonyl compounds with isatins or acenaphthenequinone in ethanol with a novel basic ionic liquid 2-hydroxyethyl ammonium acetate [H3N+CH2CH2OH] [CH3COO-] (HEAA) as catalyst. HEAA was found to be a suitable and efficient catalyst for this condensation. This method has some distinct advantages such as mild reaction conditions, short reaction time, and environmental friendliness.
Synthesis and biological evaluation of triazolothienopyrimidine derivatives as novel HIV-1 replication inhibitors
Kim, Junwon,Kwon, Jeongjin,Lee, Doohyun,Jo, Suyeon,Park, Dong-Sik,Choi, Jihyun,Park, Eunjung,Hwang, Jong Yeon,Ko, Yoonae,Choi, Inhee,Ju, Moon Kyeong,Ahn, Jiye,Kim, Junghwan,Han, Sung-Jun,Kim, Tae-Hee,Cechetto, Jonathan,Nam, Jiyoun,Ahn, Sujin,Sommer, Peter,Liuzzi, Michel,No, Zaesung,Lee, Jinhwa
, p. 153 - 157 (2013/02/23)
We identified a novel class of triazolothienopyrimidine (TTPM) compounds as potent HIV-1 replication inhibitors during a high-throughput screening campaign that evaluated more than 200,000 compounds using a cell-based full replication assay. Herein, we report the optimization of the antiviral activity in a cell-based assay system leading to the discovery of aryl-substituted TTPM derivatives (38, 44, and 45), which exhibited significant inhibition of HIV-1 replication with acceptable safety margins. These novel and potent TTPMs could serve as leads for further development.
Highly atom-economic, catalyst- and solvent-free oxidation of sulfides into sulfones using 30% aqueous H2O2
Jereb, Marjan
supporting information, p. 3047 - 3052,6 (2020/09/16)
Highly atom-efficient oxidation of sulfides into sulfones under solvent- and catalyst-free reaction conditions using a 30% aqueous solution of H 2O2 at 75 °C is reported. A structurally diverse set of phenyl alkyl-, phenyl benzyl-, benzyl alkyl-, dialkyl-, heteroaryl alkyl- and cyclic sulfides were transformed into sulfones regardless of the aggregate state and electronic nature of the substituents. In spite of the heterogeneous reaction mixtures throughout the work, no difficulties with stirring and reaction progress were noted. In numerous cases, only 10 mol% excess of H 2O2 was used, thus contributing considerably to the high atom economy of the process. Some solid substrates required a variable excess of hydrogen peroxide; however, the reactions were performed strictly without organic solvents. The transformation was demonstrated to be amenable for scale-up with both liquid and solid sulfides. In addition, isolation and purification of the crude products can be simply done with only filtration and crystallization.
Cyanuric chloride promoted oxidation of sulfides to sulfoxides or sulfones in the presence of hydrogen peroxide
Lakouraj, Moslem Mansour,Abdi, Hamid,Hasantabar, Vahid
experimental part, p. 435 - 441 (2012/06/16)
Aromatic and aliphatic sulfides are readily oxidized to sulfoxides or sulfones in high yield with 35% hydrogen peroxide in the presence of cyanuric chloride (CC) as an efficient activator. The oxidation of sulfides proceeds at room temperature and the corresponding sulfoxides or sulfones was selectively obtained by controlling the amounts of H2O2 and CC. Various sulfides possessing functional groups such as hydroxyl, methoxy, nitrile, aldehyde and olefinic double bond were successfully and selectively oxidized without affecting sensitive functionalities. [image omitted].
TiO2 nanoparticles and Preyssler-type heteropoly acid modified nano-sized TiO2: A facile and efficient catalyst for the selective oxidation of sulfides to sulfones and sulfoxides
Rahimizadeh, Mohammad,Rajabzadeh, Ghadir,Khatami, Seyed-Mola,Eshghi, Hossein,Shiri, Ali
scheme or table, p. 59 - 64 (2010/09/04)
A new and efficient synthetic method has been developed for the selective conversion of sulfides into their corresponding sulfones and sulfoxides using H2O2 in the presence of neat or Preyssler-type heteropoly acid modified nano-sized TiO2 as catalyst, respectively. The reaction was performed at room temperature with quantitative yields. The catalyst is reusable without significant loss of activity for the next oxidation reaction.
