28203-59-0Relevant articles and documents
Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones
Gayakwad, Eknath M.,Patel, Khushbu P.,Shankarling, Ganapati S.
supporting information, p. 6001 - 6009 (2019/04/17)
The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.
Influence of sulfur groups on carboxylic acid strengths
Boschmann, Erwin,Miller, Roger D.
, p. 2617 - 2619 (2018/04/30)
The relative acid strength for a series of monocarboxylic acids of the general formula R–X–(CH2)n–COOH and related dicarboxylic acids of the general formula HOOC–(CH2)n–X–(CH2)n–COOH, where R = Ph or Me, X = CH2, –S– –SO– or –SO2–; and n = 1 or 2 as appropriate; have been studied as a function of X. It is found that sulfur containing acids have lower pKa values than the corresponding carbon analogues, that the pKa is highest for the thioacids and lowest for the sulfonyl acids, that the pKas increase as n increases, and that for the dicarboxylic acid systems only the thio members show a significant reduction in pKa (2) – pKa (1) differences upon changing n from 1 to 2.
Styryl sulfones compound, its preparation method and its use as neuroprotective agents
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Paragraph 0063-0065, (2018/02/04)
The application relates to design of a novel molecule with ester group substituted by sulfone group by using a caffeic acid phenethyl ester (CAPE) with neuroprotective activity extracted from natural propolis as a primer according to bioisosterism principle and hydrogen-bond interaction theory; and the molecule has a structural general formula I, and the definition of each group is shown in the claims. The invention also relates to compound in vitroantioxidation capability evaluation, neuroprotective activity evaluation on cell level and traverse blood brain barrier ability evaluation. Activity evaluation results show that the synthesized novel compound has enhanced neuroprotective activity and can easily traverse the blood brain barrier, thus becoming a novel neuroprotective agent for treating neurodegenerative diseases.
Synthesis, characterization, and radioprotective activity of α,β-unsaturated aryl sulfone analogs and their Tempol conjugates
Zhou, Nan,Feng, Tian,Shen, Xin,Cui, Jiahui,Wu, Rangxin,Wang, Libin,Wang, Siwang,Zhang, Shengyong,Chen, Hui
supporting information, p. 1063 - 1068 (2017/07/12)
Some novel α,β-unsaturated aromatic sulfone analogs (5a-5m) and their Tempol conjugates (6a-6e) have been synthetically prepared, characterized and evaluated for their radioprotective activity under γ-ray radiation. The Tempol conjugates were characterize
Nonanebis(peroxoic acid) mediated efficient and selective oxidation of sulfide
Gayakwad, Eknath M.,Patil, Vilas V.,Shankarling, Ganapati S.
, p. 223 - 230 (2016/01/12)
Two efficient and rapid protocols for the selective oxidation of sulfide in the presence of various oxidizable functionalities such as -CHO, -CH2-OH, alkene and tert amine were investigated, using nonanebis(peroxoic acid) as an oxidant. The acetonitrile based system offers selective oxidation to sulfoxide and sulfone, while the water based system gives selective sulfone formation with a high conversion and 90-100% selectivity. Recovery and recycling of the parent acid of up to 75-80% was achieved in the water based protocol.
Design, synthesis, and biological evaluation of (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides as novel multifunctional neuroprotective agents
Ning, Xianling,Guo, Ying,Wang, Xiaowei,Ma, Xiaoyan,Tian, Chao,Shi, Xueqi,Zhu, Renzong,Cheng, Can,Du, Yansheng,Ma, Zhizhong,Zhang, Zhili,Liu, Junyi
, p. 4302 - 4312 (2014/06/09)
Novel (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides were designed and synthesized as new analogues of 1, which showed interesting multifunctional neuroprotective effects, including antioxidative and antineuroinflammatory properties. Specifically, target compounds display excellent potency in scavenging reactive free radicals and demonstrate potent effects against various kinds of toxicities, including H2O2, 6-hydroxydopamine, and lipopolysaccharide in different types of neuronal cells. The antioxidative properties of the target compounds are more potent than that of 1, and the antineuroinflammatory properties are less strong than that of 1. According to the parallel artificial membrane permeation assay for the blood-brain barrier, target compounds possess greater blood-brain barrier (BBB) permeability than 1. In short, due to improvement of the antioxidative effect, stability, and BBB permeability, (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides can thus be considered as potential multifunctional neuroprotective agents and serve as new lead candidates in the treatment of neurodegenerative diseases.
Synthesis and antioxidant activity of 1,4-[Bis(3-arylmethanesulfonyl pyrrolyl and pyrazolyl)]benzenes
Lavanya, Gopala,Padmavathi, Venkatapuram,Padmaja, Adivireddy
, p. 1200 - 1207 (2014/08/05)
A variety of (1,4-phenylene)bis(arylmethanesulfonylpyrroles and pyrazoles) were prepared by the cycloaddition of 1,3-dipolar reagents, tosylmethyl isocyanide and diazomethane to the Michael acceptor, 1,4-bis(E)-2- ((arylmethanesulfonyl)vinyl)benzene. All the compounds were evaluated for antioxidant activity. Amongst the tested compounds, one of them displayed excellent radical scavenging activity in all the three methods evaluated when compared with the standard Ascorbic acid. On the other hand, 1,4-(bis(3-arylmethanesulfonyl)-1H-pyrazol-4-yl)benzenes exhibited comparatively higher antioxidant activity than 1,4-(bis(3-arylmethanesulfonyl)-1H-pyrrol-4- yl) benzenes. In general, it was observed that compounds having methoxy substitutent on aromatic ring displayed greater antioxidant activity than the other substituents. ?2014 Sociedade Brasileira de Qui?mica.
(E)-styryl sulfone anticancer agents
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, (2008/06/13)
(E)-styryl benzylsulfones of formula I are useful as anticancer agents: wherein R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, fluoro, chloro, iodo, bromo, C1-C6 alkyl, C1-C4 alkoxy, nitro, cyano and trifluoromethyl, with the proviso that (a) R1, R2 , and R3 not all hydrogen when R4 is 2-chloro or 4-chloro; (b) when R1 and R3 are hydrogen and R2 is 4-bromo or 4-chloro, then R4 may not be 4-chloro, 4-fluoro or 4-bromo; (c) when R1 and R3 are hydrogen and R2 is 4-fluoro, then R4 may not be 4-fluoro or 4-bromo, (d) when R1 is hydrogen, and R4 is 2-fluoro, the R2 and R3 may not be 4-fluoro; and (e) when R1 is hydrogen and R3 is 4-hydrogen, 4-chloro, 4-bromo, 4-methyl or 4-methoxy, and R4 is 2-hydrogen, 2-chloro, or 2-fluoro; then R2 may not be 4-hydrogen, 4-chloro, 4-fluoro, or 4-bromo.
INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE
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, (2008/06/13)
The present invention comprises analogs of the CAAX motif of the protein Ras that is modified by farnesylation in vivo. These CAAX analogs inhibit the farnesylation of Ras. Furthermore, these CAAX analogues differ from those previously described as inhibi
Alkyl 2,2,2-trifluoroethanesulfonates (tresylates): Elimination-addition vs bimolecular nucleophilic substitution in reactions with nucleophiles in aqueous media
King, James F.,Gill, Manjinder S.
, p. 7250 - 7255 (2007/10/03)
Alkyl 2,2,2-trifluoroethanesulfonate esters (tresylates), ROSO2CH2CF3, react with aqueous base (pH ≥ 9) to give the (alkoxysulfonyl)acetic acid, ROSO2CH2COOH; with the further addition of either a primary or secondary amine or of an alkanethiol, the product is the either the corresponding amide, ROSO2CH2C(O)NR1R2, or a mixture in which the ketene dithioacetal, ROSO2CH=C(SR1)2, or the thioorthoester, ROSO2CH2C(SR1)3, may predominate. Kinetic and product studies are consistent with the following: (a) the reaction of tresylates with water is the normal sulfonic ester hydrolysis and (b) reaction with hydroxide is an (E1cB)rev process with loss of HF to yield the alkyl 2,2-difluoroethenesulfonate, ROSO2CH=CF2, which rapidly yields the observed products. Benzyl 2,2,2-trifluoroethyl sulfone reacts analogously. The relationship between these observation with small molecules and those of earlier workers with tresyl agarose is discussed.
