321578-69-2Relevant academic research and scientific papers
One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, alcohols to bis(indolyl)methanes and synthesis of pyrroles catalyzed by N-chloro reagents
Veisi, Hojat,Ataee, Meral,Fatolahi, Leila,Lotfi, Shahram
, p. 111 - 117 (2013/07/26)
A convenient synthesis of sulfonic esters from thiols and disulfides has been described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with Chloramin-T, tetra-butylammonium chloride (t-Bu4NCl) and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of bis(indolyl)methanes from alcohols using TCCA/KBr/wet-SiO2, and N-substituted pyrroles by reaction of hexane-2,5-dione with primary amines has been accomplished under mild condition with excellent yields.
One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal-Knorr synthesis of pyrrole derivatives catalyzed by TCCA
Hemmati, Saba,Mojtahedi, Mohammad Majid,Abaee, Mohammad Saeed,Vafajoo, Zahra,Saremi, Shokufe Ghahri,Noroozi, Mohammad,Sedrpoushan, Alireza,Ataee, Meral
, p. 347 - 357 (2013/09/23)
A convenient synthesis of sulfonic esters from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu4NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition with excellent yields.
Synthesis, biological evaluation, and structure-activity relationships of novel substituted N-phenyl ureidobenzenesulfonate derivatives blocking cell cycle progression in s-phase and inducing DNA double-strand breaks
Turcotte, Vanessa,Fortin, Sébastien,Vevey, Florence,Coulombe, Yan,Lacroix, Jacques,C?té, Marie-France,Masson, Jean-Yves,C.-Gaudreault, René
experimental part, p. 6194 - 6208 (2012/08/27)
Twenty-eight new substituted N-phenyl ureidobenzenesulfonate (PUB-SO) and 18 N-phenylureidobenzenesulfonamide (PUB-SA) derivatives were prepared. Several PUB-SOs exhibited antiproliferative activity at the micromolar level against the HT-29, M21, and MCF-
Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system
Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
supporting information; experimental part, p. 5095 - 5101 (2012/07/28)
Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH-). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.
ALKYLUREA DERIVATIVES ACTIVE AGAINST CANCER CELLS
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Page/Page column 24; 43, (2012/11/07)
Compounds of formula (I) : wherein A, m, n, R1, X, Y, R2, R3, R4, R5 and R6, as defined herein are provided as useful for the treatment of cancer or for the manufacture of anti-cancer agents.
SUBSTITUTED 2-IMIDAZOLIDONES AND ANALOGS
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Page/Page column 33, (2011/09/19)
Compounds of formula (I): wherein R1, R2, R3, R4, R7, R6, R7, R8, R9, A, X and Y as defined herein are provided as useful for the treatment of cancer or for
Design, synthesis, and structure-activity relationships of novel insulin receptor tyrosine kinase activators
Lum, Robert T.,Cheng, Mingshan,Cristobal, Cristina P.,Goldfine, Ira D.,Evans, Joseph L.,Keck, James G.,Macsata, Robert W.,Manchem, Vara Prasad,Matsumoto, Yukiharu,Park, Sophia J.,Rao, Sandhya S.,Robinson, Louise,Shi, Songyuan,Spevak, Wayne R.,Schow, Steven R.
scheme or table, p. 6173 - 6187 (2009/10/09)
A novel series of symmetrical ureas of [(7-amino(2-naphthyl))sulfonyl] phenylamines were designed, synthesized, and tested for their ability to increase glucose transport in mouse 3T3-L1 adipocytes, a surrogate readout for activation of the insulin receptor (IR) tyrosine kinase (IRTK). A structure-activity relationship was established that indicated glucose transport activity was dependent on the presence of two acidic functionalities, two sulfonamide linkages, and a central urea or 2-imidazolidinone core. Compound 30 was identified as a potent and selective IRTK activator. At low concentrations, 30 was able to increase the tyrosine phosphorylation of the IR stimulated by submaximal insulin. At higher concentrations, 30 was able to increase tyrosine the phosphorylation levels of the IR in the absence of insulin. When administered intraperitoneally (ip) and orally (po), 30 improved glucose tolerance in hypoinsulinemic, streptozotocin-treated rats. These data provide pharmacological validation that small molecule IRTK activators represent a potential new class of antidiabetic agents.
Competitive Reaction Pathways in the Nucleophilic Substitution Reactions of Aryl Benzenesulfonates with Benzylamines in Acetonitrile
Choi, Jin Heui,Lee, Byung Choon,Lee, Hai Whang,Lee, Ikchoon
, p. 1277 - 1281 (2007/10/03)
The reactions of aryl benzenesulfonates (YC6H4SO2OC6H4Z) with benzylamines (XC6H4CH2NH2) in acetonitrile at 65.0 deg C have been studied. The reactons proceed competitevely by S-O (kS-O) and C-O (kC-O) bond scission, but the former provides the major reaction pathway. On the basis of analysis of the Hammet and Broensted coefficients together with the cross-interaction constants ρXY, ρYZ, and ρXZ, stepwise mechanisms are proposed in which the S-O bond cleavage proceeds by rate-limiting formation of a trigonal-bipyramidal pentacoordinate (TBP-5C) intermediate, whereas the C-O bond scission takes place by rate-limiting expulsion of the sulfonate anion (YC6H4SO3-) from a Meisenheimer-type complex.
