- Design, synthesis and biological evaluation of novel phenylsulfonylurea derivatives as PI3K/mTOR dual inhibitors
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Five series of novel phenylsulfonylurea derivatives, 19a–d, 20a–d, 21a–d, 22a–d and 23a–d, bearing 4-phenylaminoquinoline scaffold were designed, synthesized and their IC50 values against four cancer cell lines (HepG-2, A549, PC-3 and MCF-7) were evaluated. Most compounds showed moderate cytotoxicity activity against the cancer cell lines. Structure–activity relationships (SARs) and pharmacological results indicated that introduction of 4-aminoquinoline scaffold and phenylsulfonylurea scaffold were beneficial for anti-tumor activity. Moreover, para-methoxyl substitution of 4-anilino moiety and para-halogen substitution of phenylsulfonylurea have different impacts on different series of compounds. Furthermore, the micromolecule group substitution in the 6-position of the quinoline ring have a slight impact on the cellular activity of the target compounds.
- Zhao, Bingbing,Lei, Fei,Wang, Caolin,Zhang, Binliang,Yang, Zunhua,Li, Wei,Zhu, Wufu,Xu, Shan
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- Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
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A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
- Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
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- Preparation method for symmetric diaryl disulfide
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The invention discloses a preparation method for symmetric diaryl disulfide. The preparation method comprises the following steps: using aromatic hydrocarbon as shown in a general formula (I) as a rawmaterial and reacting with chlorosulfonic acid to generate aryl chlorosulfonic acid, and reacting with sulfoxide chloride to synthesize aryl sulfonyl chloride as shown in a general formula (II); andpreparing the symmetric diaryl disulfide as shown in a general formula (III) under the action of a reducing agent through a reduction reaction by the aryl sulfonyl chloride as shown in the general formula (II). The disclosed preparation method for the symmetric diaryl disulfide has many advantages of low toxicity of the reaction raw material, short reaction time, cheap reagents and easy acquisition, convenient separation and purification and the like, and has very high application value and industrial production value.
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Paragraph 0028; 0029; 0030; 0031
(2019/04/17)
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- Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur
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We have studied the mechanism of solvolysis of arenesulfonyl chlorides by propan-1-ol and propan-2-ol at 303-323 K. Kinetic profiles were appropriately fit by first-order kinetics. Reactivity increases with electron-donating substituents. Ortho-alkyl substituted derivatives of arenesulfonyl chlorides show increased reactivity, but the origin of this “positive” ortho-effect remains unclear. Likely, ortho-methyl groups restrict rotation around the C-S bond, facilitating the attack of the nucleophile. No relevant reactivity changes have been found with propan-1-ol and propan-2-ol in terms of nucleophile steric effect. The existence of isokinetic relationships for all substrates suggests a single mechanism for the series. Solvolysis reactions of all substrates in both alcohols show isokinetic temperatures (Tiso) close to the working temperature range, which is an evidence of the process being influenced by secondary reactivity factors, likely of steric nature in the TS. Solvation plays a relevant role in this reaction, modulating the reactivity. In some cases, the presence of t-Bu instead of Me in para- position leads to changes in the first solvation shell, increasing the energy of the reaction (ca. 1?kJ·mol?1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan-1-ol and propan-2-ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules of the first solvation shell.
- Iazykov, Mykyta,Canle, Moisés,Santaballa, J. Arturo,Rublova, Ludmila
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supporting information
(2017/09/08)
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- Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides
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A simple and efficient method to synthesize N-chloro-N-sulfonylsulfinamides by the direct aminoxidation of arenethiols under aqueous and mild conditions is disclosed, geminally installing the oxo and amino groups on the sulfur atom of arenethiols. The products have been primarily developed as sulfinylation reagents to convert Grignard reagents into sulfoxides, and as amination reagents to convert secondary amines into hydrazine derivatives.
- Yang, Zhanhui,Xu, Wei,Wu, Qiuyue,Xu, Jiaxi
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p. 3051 - 3057
(2016/04/26)
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- PHENYL IMIDAZOL SULFONAMIDE DERIVATIVES, THE PREPARATION METHOD THEREOF AND THE WHITENING COSMETIC COMPOSITION CONTAINING THE SAME
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The present invention relates to phenyl imidazol sulfonamide derivatives expressed by the above formula I and a method for producing the same, and a whitening cosmetic composition comprising the same. More particularly, the phenyl imidazol sulfonamide der
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Page/Page column 9
(2008/06/13)
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- Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists
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The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.
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- Facile one-pot synthesis of aromatic and heteroaromatic sulfonamides
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A series of arene and heteroarene sulfonamides were prepared in one vessel from aryl and heteroaryl bromides via conversion into the corresponding Grignard reagents using either magnesium or isopropylmagnesium chloride and subsequent reaction with sulfur dioxide, sulfuryl chloride, and an amine.
- Pandya, Rina,Murashima, Takashi,Tedeschi, Livio,Barrett, Anthony G. M.
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p. 8274 - 8276
(2007/10/03)
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- Catalytic kinetic resolution of 5-alkoxy-2(5H)-furanones
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The kinetic resolution of racemic 5-alkoxy-2(5H)-furanones, using a chiral aminoalcohol catalyzed 1,4-addition of arylthiols, was examined. Using various butenolides it was shown that a γ-alkoxy substituent appears to be essential to reach high enantioselectivities whereas electron-donating substituents in the arylthiols also increase the selectivity. Cinchona alkaloids are the preferred catalysts for the kinetic resolution, with quinine and quinidine leading to the most efficient and selective thiol additions. A remarkable dilution effect and a strong dependency on the mode of addition of reactants were observed. Optimization studies are presented of the kinetic resolution of 5-methoxy-2(5H)-furanone 2 resulting in (R)-2 or (S)-2 with enantiomeric excesses exceeding 90%. A mechanism for the quinine (quinidine) catalyzed kinetic resolution is given.
- Faber, Wijnand S.,Kok, Johan,De Lange, Ben,Feringa, Ben L.
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p. 4775 - 4794
(2007/10/02)
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- REAGENTS FOR 2-TETRAHYDROTHIENYL AND 2-TETRAHYDROTHIOPYRANYL CATIONS
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O- and S-2-tetrahydrothienyl and 2-tetrahydropyranyl ethers were obtained by reaction of primary alcohols, phenols, and arenethiols with 1-p-toluenesulphonyliminotetrahydrofuran and 1-p-toluenesulphonyliminotetrahydrothiopyran in the presence of sodium hydride in dimethylformamide or by acid-catalysed transacetalysation of 2-methoxytetrahydrothiophene and 2-methoxytetrahydrothiopyran with secondary alcohols and arenethiols.
- Giovani, Elena,Napolitano, Elio,Pelosi, Paolo
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p. 257 - 260
(2007/10/02)
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- CATALYTIC SULFONYLATION OF PHENOL BY STERICALLY HINDERED SULFONYL CHLORIDES
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The sulfonylation of phenol by substituted arenesulfonyl chlorides XArSO2Cl in the presence of triethylamine in benzene was studied by potentiometric titration.A linear relation was obtained between the logaritmhs of the catalytic rate constants and the steric constants Eso of the substituents in the sulfonyl chloride.The contribution from the induction and steric effects of the substituents at position2 to the kinetics of the process was assessed.It was concluded that the steric effect plays a predominant role over the induction and resonance effects.
- Vizgert, R.V.,Maksimenko, N.N.,Rubleva, L.I.
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p. 2144 - 2146
(2007/10/02)
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- Addition of Aromatic Thiols to Conjugated Cycloalkenones, Catalyzed by Chiral β-Hydroxy Amines. A Mechanistic Study on Homogeneous Catalytic Asymmetric Synthesis
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Reactions between aromatic thiols and conjugated cycloalkenones afford optically active 3-arylthiocycloalkanones, when chiral bases are used as catalysts.This paper reports a detailed investigation into the mechanism of this catalytic asymmetric synthesis
- Hiemstra, Henk,Wynberg, Hans
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p. 417 - 430
(2007/10/02)
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