cas 51419-59-1, 4-Methylbenzylsulfonyl chloride

Articles about 51419-59-1Total 27 be found

Article title
Article abstract
Author
Journal number and time
Download

Preparation method of novel abscisic acid agonist AM1
The invention discloses a preparation method of a novel abscisic acid agonist AM1, and relates to chemical synthesis. The preparation method comprises the following steps: taking cheap quinoline as a raw material, and preparing a key intermediate 1-propyl
-
Paragraph 0017; 0022

(2021/05/12)

Design, synthesis and biological evaluation of novel N-sulfonylamidine-based derivatives as c-Met inhibitors via Cu-catalyzed three-component reaction
In our continuing efforts to develop novel c-Met inhibitors as potential anticancer candidates, a series of new N-sulfonylamidine derivatives were designed, synthesized via Cu-catalyzed multicomponent reaction (MCR) as the key step, and evaluated for their in vitro biological activities against c-Met kinase and four cancer cell lines (A549, HT-29, MKN-45 and MDA-MB-231). Most of the target compounds showed moderate to significant potency at both the enzyme-based and cell-based assay and possessed selectivity for A549 and HT-29 cancer cell lines. The preliminary SAR studies demonstrated that compound 26af (c-Met IC50 = 2.89 nM) was the most promising compound compared with the positive foretinib, which exhibited the remarkable antiproliferative activities, with IC50 values ranging from 0.28 to 0.72 μM. Mechanistic studies of 26af showed the anticancer activity was closely related to the blocking phosphorylation of c-Met, leading to cell cycle arresting at G2/M phase and apoptosis of A549 cells by a concentration-dependent manner. The promising compound 26af was further identified as a relatively selective inhibitor of c-Met kinase, which also possessed an acceptable safety profile and favorable pharmacokinetic properties in BALB/c mouse. The favorable drug-likeness of 26af suggested that N-sulfonylamidines may be used as a promising scaffold for antitumor drug development. Additionally, the docking study and molecular dynamics simulations of 26af revealed a common mode of interaction with the binding site of c-Met. These positive results indicated that compound 26af is a potential anti-cancer candidate for clinical trials, and deserves further development as a selective c-Met inhibitor.
Fang, Sen-Biao,Li, Hui-Jing,Nan, Xiang,Wu, Rui,Wu, Yan-Chao,Zhang, Jing,Zhang, Zhi-Zhou
(2020/06/04)

Alkyne Linchpin Strategy for Drug:Pharmacophore Conjugation: Experimental and Computational Realization of a Meta-Selective Inverse Sonogashira Coupling
The late-stage functionalization (LSF) of pharmaceutical and agrochemical compounds by the site-selective activation of C-H bonds provides access to diverse structural analogs and expands synthetically-accessible chemical space. We report a C-H functionalization LSF strategy that hinges on the use of an alkyne linchpin to assemble conjugates of sp2-rich marketed pharmaceuticals and agrochemicals with sp3-rich 3D fragments and natural products. This is accomplished through a template-assisted inverse Sonogashira reaction that displays high levels of selectivity for the meta position. This protocol is also amenable to distal structural modifications of α-amino acids. The transformation of alkyne functionality to other functional groups further highlights the applicative potential. Computational and experimental mechanistic studies shed light on the detailed mechanism. Turnover-limiting 1,2-migratory insertion of the bromoalkyne coupling partner occurs after relatively fast C-H activation. While this insertion occurs unselectively, regioconvergence results from one of the adducts undergoing a 1,2-trialkylsilyl migration to form the alkynylated product. A heterobimetallic Pd-Ag transition structure is essential for product formation in the β-bromide elimination step.
Bhowmick, Suman,Guin, Srimanta,Kumar Singh, Vikas,Maiti, Debabrata,Paton, Robert S.,Porey, Sandip,Zhang, Xinglong
supporting information
p. 3762 - 3774
(2020/03/10)

Optimization of P2Y12 Antagonist Ethyl 6-(4-((Benzylsulfonyl)carbamoyl)piperidin-1-yl)-5-cyano-2-methylnicotinate (AZD1283) Led to the Discovery of an Oral Antiplatelet Agent with Improved Druglike Properties
P2Y12 antagonists are widely used as antiplatelet agents for the prevention and treatment of arterial thrombosis. Based on the scaffold of a known P2Y12 antagonist AZD1283, a series of novel bicyclic pyridine derivatives were designed and synthesized. The cyclization of the ester substituent on the pyridine ring to the ortho-methyl group led to lactone analogues of AZD1283 that showed significantly enhanced metabolic stability in subsequent structure-pharmacokinetic relationship studies. The metabolic stability was further enhanced by adding a 4-methyl substituent to the piperidinyl moiety. Compound 58l displayed potent inhibition of platelet aggregation in vitro as well as antithrombotic efficacy in a rat ferric chloride model. Moreover, 58l showed a safety profile that was superior to what was observed for clopidogrel in a rat tail-bleeding model. These results support the further evaluation of compound 58l as a promising drug candidate.
Kong, Deyu,Xue, Tao,Guo, Bin,Cheng, Jianjun,Liu, Shunyin,Wei, Jianhai,Lu, Zhengyu,Liu, Haoran,Gong, Guoqing,Lan, Tian,Hu, Wenhao,Yang, Yushe
supporting information
p. 3088 - 3106
(2019/04/01)

Method for rapidly preparing abscisic acid receptor stimulant
The invention discloses a method for rapidly preparing an abscisic acid receptor stimulant and relates to a chemical synthesis and plant growing regulation technology. The method is characterized in that the two-step one-pot strategy is adopted, 4-methylb
-
Paragraph 0024

(2019/05/08)

HIGH STRESS RESISTANT PLANT GROWTH REGULATOR AND PREPARATION METHOD AND USE THEREOF
Disclosed are a high stress resistant plant growth regulator and a preparation and use thereof. In particular, the compound provided by the present invention is an ABA substitute for significantly improving the stress resistance of plants, and therefore has a very wide application prospect.
-
Paragraph 0322-0323

(2019/01/15)

Design, synthesis and evaluation of sulfonylurea-containing 4-phenoxyquinolines as highly selective c-Met kinase inhibitors
Deregulation of receptor tyrosine kinase c-Met has been reported in human cancers and is considered as an attractive target for small molecule drug discovery. In this study, a series of 4-phenoxyquinoline derivatives bearing sulfonylurea moiety were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against tested four cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant potency as compared with foretinib, with the most promising compound 13x (c-Met kinase IC50 = 1.98 nM) demonstrated relatively good selectivity versus 10 other tyrosine kinases and remarkable cytotoxicities against HT460, MKN-45, HT-29 and MDA-MB-231 with IC50 values of 0.055 μM, 0.064 μM, 0.16 μM and 0.49 μM, respectively. The preliminary structure activity relationships indicated that a sulfonylurea moiety as linker as well as mono-EGWs (such as R1 = 4-F) on the terminal phenyl rings contributed to the antitumor activity.
Nan, Xiang,Jiang, Yi-Fan,Li, Hui-Jing,Wang, Jun-Hu,Wu, Yan-Chao
supporting information
p. 2801 - 2812
(2019/05/15)

Olefination with Sulfonyl Halides and Esters: E-Selective Synthesis of Alkenes from Semistabilized Carbanion Precursors
Carbanions of sulfonyl halides and activated sulfonates add to carbonyl compounds, and so-formed aldol-type adducts spontaneously fragment into olefins. This transformation mimics the one-pot Julia olefination with (hetero)aryl sulfones, but the mechanism of fragmentation involves a four-membered intermediate, typical for reactivity of phosphorus reagents. Moreover, in contrast to the reactions of sulfones, sulfonates of fluorinated alcohols (TFE and HFI) produce byproducts that are easily removed during workup. In our report, we focus on reactions of unstabilized and semistabilized carbanion precursors: alkylsulfonates, and allyl- and benzylsulfonates, respectively. In particular for semistabilized systems, olefins were synthesized as predominant E isomers in good yields. The presented studies reveal that optimal reaction conditions, including the type of base and alcohol groups of the sulfonates, are different depending on stabilization of the carbanion precursors and structure of the carbonyl substrates. The practical synthetic guide is supplemented with a discussion of the mechanism, based on reactivity studies of intermediates and identification of side-products.
Górski, Bartosz,Basiak, Dariusz,Talko, Alicja,Basak, Tymoteusz,Mazurek, Tomasz,Barbasiewicz, Micha?
supporting information
p. 1774 - 1784
(2018/04/27)

Design, Sustainable Synthesis, and Programmed Reactions of Templated N-Heteroaryl-Fused Vinyl Sultams
A de novo design and synthesis of N-heteroaryl-fused vinyl sultams as templates for programming chemical reactions on vinyl sultam periphery or (hetero)aryl ring is described. The key features include rational designing and sustainable synthesis of the template, customized reactions of vinyl sultams at C=C bond or involving N-S bond cleavage, and reactions on the periphery of the heteroaryl ring for late-stage diversification. The simple, easy access to the template coupled with opportunities for the synthesis of diversely functionalized heterocyles from a single template constitutes a rare study in contemporary organic synthesis.
Laha, Joydev K.,Sharma, Shubhra,Kirar, Seema,Banerjee, Uttam C.
p. 9350 - 9359
(2017/09/23)

Photocatalytic Radical Alkylation of Electrophilic Olefins by Benzylic and Alkylic Zinc-Sulfinates
Alkyl radicals are obtained by photocatalytic oxidation of readily prepared or commercially available zinc sulfinates. The convenient benzylation and alkylation of a variety of electron-poor olefins triggered by the iridium(III) complex 6 Ir[dF(CF3)ppy]2(dtbbpy)PF6 as photocatalyst is described. Moreover, it is shown that zinc sulfinates can be used for facile nonradical sulfonylation reactions with highly electrophilic Michael acceptors.
Gualandi, Andrea,Mazzarella, Daniele,Ortega-Martínez, Aitor,Mengozzi, Luca,Calcinelli, Fabio,Matteucci, Elia,Monti, Filippo,Armaroli, Nicola,Sambri, Letizia,Cozzi, Pier Giorgio
p. 5357 - 5362
(2017/08/17)

Rhodium-Catalyzed meta-C?H Functionalization of Arenes
Rhodium-catalyzed ortho-C?H functionalization is well known in the literature. Described herein is the Xphos-supported rhodium catalysis of meta-C?H olefination of benzylsulfonic acid and phenyl acetic acid frameworks with the assistance of a para-methoxy-substituted cyano phenol as the directing group. Complete mono-selectivity is observed for both scaffolds. A wide range of olefins and functional groups attached to arene are tolerated in this protocol.
Bera, Milan,Agasti, Soumitra,Chowdhury, Rajdip,Mondal, Rahul,Pal, Debasis,Maiti, Debabrata
supporting information
p. 5272 - 5276
(2017/04/27)

Tert -Butyl Hypochlorite Mediated Oxidative Chlorination of S -Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides
Under neutral conditions, a variety of S-alkylisothiourea salts were smoothly converted into the corresponding sulfonyl chlorides through tert-butyl chlorite mediated oxidative chlorination in good to excellent yields after simple purification. In addition to the environmental and procedural advantages of this method, the neutral conditions potentially make it applicable to substrates that bear acid-sensitive functional groups. For example, the Cbz-protected 2-aminoethanesulfonyl chloride could be synthesized in moderate to good yields under the current neutral conditions, and the acid-sensitive Cbz-protecting group was not affected.
Qiu, Kui,Wang, Rennan
p. 3186 - 3190
(2015/10/19)

Palladium(II)-Catalyzed meta-C-H Olefination: Constructing Multisubstituted Arenes through Homo-Diolefination and Sequential Hetero-Diolefination
Divinylbenzene derivatives represent an important class of molecular building blocks in organic chemistry and materials science. Reported herein is the palladium-catalyzed synthesis of divinylbenzenes by meta-C-H olefination of sulfone-based arenes. Successful sequential olefinations in a position-selective manner provided a novel route for the synthesis of hetero-dialkenylated products, which are difficult to access using conventional methods. Additionally, 1,3,5-trialkenylated compounds can be generated upon successful removal of the directing group. Jockeying for position: Reported herein is the palladium-catalyzed synthesis of mono- and divinylbenzenes by meta-C-H olefination of benzyl sulfones. Successful sequential olefinations in a position-selective manner provided a novel route for the synthesis of hetero-dialkenylated products, which are difficult to access using conventional methods. DG=directing group.
Bera, Milan,Maji, Arun,Sahoo, Santosh K.,Maiti, Debabrata
supporting information
p. 8515 - 8519
(2015/11/27)

Preparation of alkanesulfonyl chlorides from s-alkyl isothiourea salts via n-chlorosuccinimide mediated oxidative chlorosulfonation
-
Yang, Zhanhui,Xu, Jiaxi
p. 116 - 124
(2014/04/17)

Clean and economic synthesis of alkanesulfonyl chlorides from S-alkyl isothiourea salts via bleach oxidative chlorosulfonation
A simple procedure for clean and economic synthesis of alkanesulfonyl chlorides via bleach-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is disclosed. This procedure is environment- and worker-friendly with the advantages of readily accessible materials and reagents, simple and safe operations, easy purification without chromatography, and affords high yields of up to 99%.
Yang, Zhanhui,Zhou, Bingnan,Xu, Jiaxi
p. 225 - 229
(2014/03/21)

Convenient and environment-friendly synthesis of sulfonyl chlorides from S -alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation
A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from 'waste water' can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable. Georg Thieme Verlag Stuttgart, New York.
Yang, Zhanhui,Xu, Jiaxi
p. 1675 - 1682
(2013/07/27)

Simple synthesis of sulfonyl chlorides from thiol precursors and derivatives by NaClO2-mediated oxidative chlorosulfonation
A simple method to synthesize diverse sulfonyl chlorides through NaClO 2-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is presented. The approach features safe operation, environmental friendliness, convenient purification procedures, and delivers high yields of up to 96%. The procedure is also applicable to substrates such as thiols, disulfides, thioacetates, and xanthates. It is a versatile and convenient method for the synthesis of various sulfonyl chlorides from different thiol precursors and derivatives. Georg Thieme Verlag Stuttgart, New York.
Yang, Zhanhui,Zheng, Yongpeng,Xu, Jiaxi
supporting information
p. 2165 - 2169
(2013/10/22)

Access to a wide range of sultams by cyclodialkylation of α-substituted methanesulfonanilides
A wide range of five- and six-membered sultams bearing an α-ethoxycarbonyl-α-methyl substituent or an α-aryl group (17 examples) were synthesized by the cyclodialkylation of α-substituted methanesulfonanilides with α,ω-dihaloalkanes in the presence of K2CO3 or under phase-transfer catalysis (PTC) conditions. Upon treatment with K2CO3 in N,N-dimethylformamide (DMF) or NaH in dimethyl sulfoxide (DMSO), N-(2,3-dibromopropyl)-α- toluenesulfonanilides furnished different 1,3-diaryl-2-thia-3-azabicyclo[3.1.0] hexane 2,2-dioxides in good to excellent yields (51-88 %, 16 examples). The 4-methoxyphenyl (PMP) group was easily removed from the sultam nitrogen atom by treatment of the corresponding bicyclic sultams with cerium(IV) ammonium nitrate in acetonitrile (71-84 % yield, 6 examples). The intermolecular cyclodialkylation of α-substituted methanesulfonamides constitutes a simple and efficient route to five- and six-membered sultams with α-ethoxycarbonyl-α-methyl or α-aryl substitution. The intramolecular cyclodialkylation of N-(2,3-dibromopropyl)-α- toluenesulfanilides readily leads to bicyclic sultams bearing a cyclopropane ring. Copyright
Rassadin, Valentin A.,Grosheva, Daria S.,Arefeva, Irina A.,Tomashevskiy, Aleksandr A.,Sokolov, Victor V.,De Meijere, Armin
supporting information
p. 5028 - 5037,10
(2020/08/24)

Convenient one-pot synthesis of sulfonamides from thiols and disulfides using 1,3-dichloro-5,5-dimethylhydantoin (DCH)
A convenient synthesis of sulfonamides from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with 1,3-dichloro-5,5-dimethylhydantoin (DCH) under Nbenzyl-trimethylammonium chloride and water. The sulfonyl chlorides are then further allowed to react with excess amine in the same reaction vessel.
Veisi, Hojat
experimental part
p. 383 - 386
(2012/04/23)

Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N -chlorosuccinimide
A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water. The sulfonyl chlorides are then further allowed to react with excess amine or sodium azide in the same reaction vessel. Georg Thieme Verlag Stuttgart - New York.
Veisi, Hojat,Ghorbani-Vaghei, Ramin,Hemmati, Saba,Mahmoodi, Jafar
experimental part
p. 2315 - 2320
(2011/10/13)

Arylalkane-sulfonamides having endothelin-antagonist activity
The invention relates to novel aryl-alkane-sulfonamides and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists.
-
(2008/06/13)

Synthesis of α-fluorosulfonamides by electrophilic fluorination
(Chemical Equation Presented) α-Fluorosulfonamides were prepared by electrophilic fluorination of tertiary sulfonamides using N- fluorobenzenesulfonimide as fluorinating agent and utilizing the dimethoxybenzyl group (DMB) as a new sulfonamide protecting g
Hill, Bryan,Liu, Yong,Taylor, Scott D.
p. 4285 - 4288
(2007/10/03)

Nucleophilic Substitution Reaction of Phenylmethanesulfonyl Halides with Anilines
Kinetic studies on the nucleophilic substitution reaction of Y-substituted phenylmethanesulfonyl halides with X-substituted anilines in methanol-acetonitrile have been carried out in order to elucidate the reaction mechanism.The phenylmethanesulfonyl fluorides (PSF) had markedly lower rates and smaller magnitudes of ρX and ρY values compared with those for the chlorides (PSC).On the contrary, however, the magnitude of the cross-interaction constant ρXY was greater for PSF than for PSC, so that the degree of bond making in the transition state is actually greater in the reaction of PSF as compared with that for PSC.We have thus demonstrated that extensive charge transfer from a nucleophile to a substrate does not necessarily mean a tight bond in the transition state.Moreover the nonzero ρXY values obtained for both PSC and PSF are taken as evidence in support of a common, associative SN2 mechanism for the two halides.
Lee, Ikchoon,Kang, Han Keun,Lee, Hai Whang
p. 7472 - 7477
(2007/10/02)

DESULFONYLATION OF ARYLMETHANESULFONYL CHLORIDES CATALYZED BY DICLHOROTRIS(TRIPHENYLPHOSPHINE)RUTHENIUM(II)
Reactions of arylmethanesulfonyl chlorides catalyzed by dichlorotris(triphenylphosphine)ruthenium(II) (1) have been studied.Desulfonylation occurred when arylmethanesulfonyl chlorides were treated with catalytic amounts of the ruthenium(II) catalyst to give chloromethylarene in high yields.No addition of the sulfonyl chloride to olefin was observed when the reaction was carried out in the presence of an equimolar amount of an olefin such as styrene.However, the rate of disappearance of the sulfonyl chloride was accelerated by addition of an olefin.The desulfonylation is assumed to proceed by a redox transfer promoted homolytic mechanism in the coordination sphere of the catalyst.In the presence of large excess of styrenes, arylmethanesulfonyl chlorides added to the olefins to give 1:1 adducts competitively with the desulfonylation yielding chloromethylarenes.
Kamigata, Nobumasa,Suzuki, Norihiro,Kobayashi, Michio
p. 139 - 144
(2007/10/02)

REACTION OF ARYLMETHANESULFONYL AND STYRYLMETHANESULFONYL CHLORIDES WITH TRIETHYLAMINE
A series of arylmethanesulfonyl chlorides were treated with triethylamine in THF to give stilbenes in excellent yields.Workup of the mixtures below 10 deg C permits isolation of stilbene episulfones which on warming decompose to yield the corresponding stilbenes stereospecifically.Application of the reaction to 9-fluorenylsulfonyl chloride affords bifluorenylidene, while trans-styrylmethanesulfonyl chloride gives 4,5-dihydro-4,5-diphenylthiepin 1,1-dioxide and 1,6-diphenylhexatriene.
Nakayama, Juzo,Tanuma, Mitsuru,Honda, Yoshiko,Hoshino, Masamatsu
p. 4553 - 4556
(2007/10/02)

Protected amino acids or peptides
In an amino acid having ω-amino group protected with a protective group or a peptide having the residue of such a protected amino acid, the improvement according to which the protective group is p-methylbenzylsulfonyl group. The ω-amino acids protected with p-methylbenzylsulfonyl or the peptides having residues of such protected amino acids are useful for production of various peptides by liquid phase method as well as by solid-phase method, because the protective group has specific selectivity of remaining stable under the conditions commonly employed in the removal of α-aminoprotecting group but is cleaved smoothly in a good yield by hydrogen fluoride without exerting untoward unfluences upon peptides.
-
(2008/06/13)