cas 4563-33-1, Benzenemethanesulfonamide | Articles data

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Sulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor-Acceptor Activation of Pyridinium Salts
Synthetically versatile alkyl sulfinates can be prepared from readily available amines, using Katritzky pyridinium salt intermediates. In a catalyst-free procedure, primary, secondary, and benzylic alkyl radicals are generated by photoinduced or thermally induced single-electron transfer (SET) from an electron donor-acceptor (EDA) complex, and trapped by SO2 to generate sulfonyl radicals. Hydrogen atom transfer (HAT) from Hantzsch ester gives alkyl sulfinate products, which are used to prepare a selection of medicinal chemistry relevant sulfonyl-containing motifs.
Andrews, Jonathan A.,Pantaine, Lo?c R. E.,Palmer, Christopher F.,Poole, Darren L.,Willis, Michael C.
supporting information
p. 8488 - 8493
(2021/11/01)

Primary Sulfonamide Synthesis Using the Sulfinylamine Reagent N-Sulfinyl- O-(tert-butyl)hydroxylamine, t-BuONSO
Sulfonamides have played a defining role in the history of drug development and continue to be prevalent today. In particular, primary sulfonamides are common in marketed drugs. Here we describe the direct synthesis of these valuable compounds from organometallic reagents and a novel sulfinylamine reagent, t-BuONSO. A variety of (hetero)aryl and alkyl Grignard and organolithium reagents perform well in the reaction, providing primary sulfonamides in good to excellent yields in a convenient one-step process.
Davies, Thomas Q.,Hall, Adrian,Skolc, David,Tilby, Michael J.,Willis, Michael C.
supporting information
p. 9495 - 9499
(2020/12/21)

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
p. 2801 - 2812
(2019/05/15)

High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides
In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.
Sohrabnezhad, Samira,Bahrami, Kiumars,Hakimpoor, Farahman
p. 256 - 264
(2019/02/06)

A general iodine-mediated synthesis of primary sulfonamides from thiols and aqueous ammonia
A general and efficient methodology for preparing primary sulfonamides has been developed. In the presence of iodine as the catalyst and TBHP (70% in water) as the oxidant, a wide range of primary sulfonamides were prepared from the corresponding thiols and aqueous ammonia in moderate to good yields.
Feng, Jian-Bo,Wu, Xiao-Feng
supporting information
p. 6951 - 6954
(2016/07/30)

One-pot synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T
A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine-T (=N-chlorotosylamide=N-chloro-4- methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.
Maleki, Behrooz,Hemmati, Saba,Tayebee, Reza,Salemi, Sirous,Farokhzad, Yasaman,Baghayeri, Mehdi,Zonoz, Farrokhzad Mohammadi,Akbarzadeh, Elahe,Moradi, Rohollah,Entezari, Azam,Abdi, Mohammad Reza,Ashrafi, Samaneh Sedigh,Taimazi, Fereshteh,Hashemi, Majid
p. 2147 - 2151
(2013/12/04)

Development of a Multi-Kilogram-Scale Synthesis of AZD1283: A Selective and Reversible Antagonist of the P2Y12 Receptor
Ethyl 6-chloro-5-cyano-2-methylnicotinate (4) was coupled with 4-piperidinecarboxylic acid (isonipecotic acid) in 81% yield to pyridine acid 10. An amide coupling between 10 and benzylsulfonamide (6) afforded AZD1283 (1) in 79% yield using CDI as coupling reagent. The synthesis has been developed and scaled up to 20 kg batches of 1, supporting preclinical and clinical studies. Development work towards 2-chloropyridine 4 and benzylsulfonamide (6) is included.
Andersen, Soren M.,Aurell, Carl-Johan,Zetterberg, Fredrik,Bollmark, Martin,Ehrl, Robert,Schuisky, Peter,Witt, Anette
p. 1543 - 1551
(2014/01/06)

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
p. 383 - 386
(2012/04/23)

Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system
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.
Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
p. 5095 - 5101
(2012/07/28)

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
p. 2315 - 2320
(2011/10/13)

Direct conversion of thiols and disulfides into sulfonamides
The H2O2-ZrCl4 reagent system is used as a new and efficient reagent for the conversion of thiols and disulfides into sulfonamides. The protocol offers several advantages such as excellent yields of products and extremely fast reactions at room temperature. The reagent system is very easy to handle and is environmentally safe and economical.
Bahrami, Kiumars,Khodaei, Mohammad M.,Soheilizad, Mehdi
supporting information; experimental part
p. 4843 - 4846
(2010/10/02)

Direct conversion of thiols to sulfonyl chlorides and sulfonamides
(Chemical Equation Presented) H2O2 in combination with SOCl2 proved to be a highly reactive reagent for the direct oxidative conversion of thiol derivatives to the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Upon reaction with amines, the corresponding sulfonamides were obtained in excellent yields and in very short reaction times.
Bahrami, Kiumars,Khodaei, Mohammad M.,Soheilizad, Mehdi
supporting information; experimental part
p. 9287 - 9291
(2010/03/04)

Biphenyl- and terphenyl-based recyclable organic trivalent iodine reagents
Biphenyl- and terphenyl-based recyclable trivalent iodine reagents, such as 4-bromo-4′-(diacetoxyiodo)biphenyl, 4,4′-bis(diacetoxyiodo)biphenyl, 1,4-bis[4-(diacetoxyiodo)phenyl]benzene, 4-bromo-4′-[(hydroxy)(tosyloxy)iodo]biphenyl, 4,4′-bis[(hydroxy)(tosyloxy)iodo]biphenyl, were simply prepared and their reactivities for the oxidative rearrangement of ketones to esters, TEMPO-mediated oxidation of alcohols to aldehydes or ketones, oxidative dealkylation of N-alkylsulfonamides to sulfonamides, and α-tosyloxylation of ketones were compared with p-(diacetoxyiodo)toluene and p-[(hydroxy)(tosyloxy)iodo]toluene to show the same reactivities and, moreover, the biphenyl- and terphenyl-based iodoarenes formed were recovered by simple filtration of the reaction mixture in every reaction. Thus, these biphenyl- and terphenyl-based trivalent iodine reagents can be used as the recyclable reagents.
Moroda, Atsushi,Togo, Hideo
p. 12408 - 12414
(2007/10/03)

Synthesis of α-fluoro- And α,α-difluoro- benzenemethanesulfonamides: New inhibitors of carbonic anhydrase
Direct fluorination of arenemethanesulfonamide anions under mild conditions and in high yield has been accomplished using N-fluorobisbenzenesulfonimide, NFSi, on carbanions of N-tert-butyl- and N-bis-(4-methoxyphenyl-methyl)- benzenemethanesulfonamides giving novel α-fluoro- and α,α- difluoro-benzenemethanesulfonamides respectively: IC50 and pK a data show that α-halogenation enhances sulfonamide acidity incrementally and correlates well with increased carbonic anhydrase inhibition, while lipophilicity is also enhanced.
Blackburn, G. Michael,Tuerkmen, Hasan
p. 225 - 226
(2007/10/03)

N-Acyl arylsulfonamides as novel, reversible inhibitors of human steroid sulfatase
Steroid sulfatase (STS) is an attractive target for a range of oestrogen- and androgen-dependent diseases. In search of novel chemotypes of STS inhibitors, we had previously identified nortropinyl-arylsulfonylureas 1; however, while these compounds were good inhibitors of purified STS (lowest Ki = 76 nM), they showed only weak inhibition of STS activity in cells (lowest IC50 around 2 μM). Extended structure-activity relationship studies involving modification of the phenylacetyl side chain and replacement of the nortropine element by simpler scaffolds led to the discovery of N-acyl arylsulfonamides, more specifically N-(Boc-piperidine-4-carbonyl)- benzenesulfonamides, as STS inhibitors, some of which exhibit improved cellular potency (best IC50 = 270 nM).
Lehr, Philipp,Billich, Andreas,Wolff, Barbara,Nussbaumer, Peter
p. 1235 - 1238
(2007/10/03)

Novel N-dealkylation of N-alkyl sulfonamides and N,N-dialkyl sulfonamides with periodic acid catalyzed by chromium(III) acetate hydroxide
Chromium(III) acetate hydroxide has been found to be an efficient catalyst for N-dealkylation of N-alkyl sulfonamides and N,N-dialkyl sulfonamides to furnish sulfonamides in good to excellent yields with periodic acid in acetonitrile at room temperature.
Xu, Liang,Zhang, Suhong,Trudell, Mark L.
p. 1901 - 1904
(2007/10/03)

In vivo imaging
A positron emission tomography (PET)-ready library of candidate pharmaceutical agents is provided which can be prepared by a multistep process wherein the final or penultimate step is a reaction using a PET-ready reagent or a plurality of PET-ready reagents. Methods of preparing and using the libraries are also provided.
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(2008/06/13)

Autoinducer compounds
Autoinducer compounds which enhance gene expression in a wide variety of microorganisms, therapeutic compositions and therapeutic methods wherein gene expression within microorganisms is regulated are disclosed.
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(2008/06/13)

Autoinducer compounds
Autoinducer compounds which enhance gene expression in a wide variety of microorganisms, therapeutic compositions and therapeutic methods wherein gene expression within microorganisms is regulated are disclosed.
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(2008/06/13)

Cyclic sulfonyl compounds as inhibitors of metalloproteases
The present application describes novel cyclic sulfonyl derivatives of formula I: or pharmaceutically acceptable salt forms thereof, wherein ring B is a 5-7 membered cyclic system containing from 0-2 heteroatoms selected from O, N, NRa, and S(O)p, and 0-1 carbonyl groups and the other variables are defined in the present specification, which are useful as metalloprotease inhibitors.
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(2008/06/13)

Oxidatively sonochemical dealkylation of various N-alkylsulfonamides to free sulfonamides and aldehydes
Various N-alkylsulfonamides were easily dealkylated to give the corresponding free sulfonamides in moderate to good yields in the presence of (diacetoxyiodo)benzene and iodine under ultrasonic irradiation. Application of this methodology to various N-prot
Katohgi, Masashi,Togo, Hideo
p. 7481 - 7486
(2007/10/03)

THE PREPARATION AND USE OF ORTHO-SULFONAMIDO ARYL HYDROXAMIC ACIDS AS MATRIX METALLOPROTEINASE AND TACE INHIBITORS
The present invention relates to the discovery of novel, low molecular weight, non-peptide inhibitors of matrix metalloproteinases (e.g. gelatinases, stromelysins and collagenases) and TNF- alpha converting enzyme (TACE, tumor necrosis factor- alpha converting enzyme) which are useful for the treatment of diseases in which these enzymes are implicated such as arthritis, tumor growth and metastasis, angiogenesis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, proteinuria, aneurysmal aortic disease, degenerative cartilage loss following traumatic joint injury, demyelinating diseases of the nervous system, graft rejection, cachexia, anorexia, inflammation, fever, insulin resistance, septic shock, congestive heart failure, inflammatory disease of the central nervous system, inflammatory bowel disease, HIV infection, age related macular degeneration, diabetic retinopathy, proliferative vitreoretinopathy, retinopathy of prematurity, ocular inflammation, keratoconus, Sjogren's syndrome, myopia, ocular tumors, ocular angiogenesis/neovascularization. The TACE and MMP inhibiting ortho-sulfonamido aryl hydroxamic acids of the present invention are represented by formula (I) where the hydroxamic acid moiety and the sulfonamido moiety are bonded to adjacent carbons on group A where: A is phenyl or naphthyl, optionally substituted by R, R, R and R; Z is aryl, heteroaryl, or heteroaryl fused to a phenyl, where aryl is phenyl or naphthyl optionally substituted by R, R, R and R; heteroaryl is a 5-6 membered heteroaromatic ring having from 1 to 3 heteroatoms independently selected from N, O and S, and optionally substituted by R, R, R and R; and when heteroaryl is fused to phenyl, either or both of the rings can be optionally substituted by R, R, R and R; and R, R, R, R, R, R, R, R and R are described in the specification, and the pharmaceutically acceptable salts thereof and the optical isomers and diastereomers thereof.
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(2008/06/13)

Novel sonochemical dealkylation of N-alkylsulfonamides in the presence of (diacetoxyiodo)benzene and iodine
Various N-alkylsulfonamides were easily dealkylated in moderate to good yields by the ultrasonic irradiation in the presence of (diacetoxyiodo)benzene and iodine.
Katohgi, Masashi,Yokoyama, Masataka,Togo, Hideo
p. 1055 - 1057
(2007/10/03)

PREPARATION AND USE OF ORTHO-SULFONAMIDO ARYL HYDROXAMIC ACIDS AS MATRIX METALLOPROTEINASE AND TACE INHIBITORS
The present invention relates to the discovery of novel, low molecular weight, non-peptide inhibitors of matrix metalloproteinases (e. g. gelatinases, stromelysins and collagenases) and TNF-α converting enzyme (TACE, tumor necrosis factor-α converting enzyme) which are useful for the treatment of diseases in which these enzymes are implicated such as arthritis, tumor growth and metastasis, angiogenesis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, proteinuria, aneurysmal aortic disease, degenerative cartilage loss following traumatic joint injury, demyelinating diseases of the nervous system, graft rejection, cachexia, anorexia, inflammation, fever, insulin resistance, septic shock, congestive heart failure, inflammatory disease of the central nervous system, inflammatory bowel disease, HIV infection, age related macular degeneration, diabetic retinopathy, proliferative vitreoretinopathy, retinopathy of prematurity, ocular inflammation, keratoconus, Sjogren's syndrome, myopia, ocular tumors, ocular angiogenesis/neovascularization. The TACE and MMP inhibiting ortho-sulfonamido aryl hydroxamic acids of the present invention are represented by the formula STR1 where the hydroxamic acid moiety and the sulfonamido moiety are bonded to adjacent carbons on group A.
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(2008/06/13)

Thermosensitive recording material
A thermosensitive recording material having a high whiteness and capable of forming clear colored images with an excellent resistance to oil and plasticizers is provided with a thermosensitive colored image-forming layer formed on a substrate sheet and comprising a substantially colorless dye precursor, a binder and a color-developing agent comprising at least one aromatic compound having, per molecule thereof, at least two functional sulfonylamino(thio)carbonylamino groups of the formula (I): wherein X is an oxygen or sulfur atom.
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(2008/06/13)

Asymmetric synthesis of α-functionalized primary sulfonamides
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Davis,Zhou,Carroll
p. 4890 - 4896
(2007/10/02)

SYNTHESIS, STRUCTURE, AND PROPERTIES OF COMPOUNDS WITH A CHALCOGEN-NITROGEN BOND XIII. THE EFFECT OF THE NATURE OF THE CHALCOGEN ATOM ON THE ABILITY OF N-SULFONYLCHALCOGENIMIDES TO OXIDIZE HYDROQUINONE AND ITS DERIVATIVES
N-Sulfonyldiphenylsulfimides do not react with hydroquinone, 2,5-di(tert-butyl)hydroquinone, and tetrahydroxy-p-benzoquinone even with prolonged heating above 150 deg C.Selenimides and tellurimides with analogous structures oxidize these compounds to the corresponding quinones.The oxidizing power of the tellurimides in the investigated reations is higher than that of the selenimides.This is explained by the increased polarity of the chalcogen-nitrogen bond and, consequently, the ease of its cleavage in N-sulfonylchalcogenimides in the series: S Se Te.The intermediate products from the reaction of the tellurium derivatives with hydroquinone, i.e., polymeric diaryltellurium p-hydroxyphenolates, were isolated.
Naddaka, V. I.,Avanesyan, K. V.,Cherkinskaya, M. L.
p. 705 - 711
(2007/10/02)

REACTION OF N-SULFONYLDIARYLTELLURIMIDES WITH HYDROQUINONE
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Naddaka, V. I.,Avanesyan, K. V.,Nesterova, M. A.,Minkin, V. I.
p. 802 - 803
(2007/10/02)

The reaction of sulfinic acid salts with hydroxylamine-O-sulfonic acid. A useful synthesis of primary sulfonamides
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Graham,Scholz
p. 1031 - 1032
(2007/10/02)

Intramolecular sulphonyl-amidomethylation. Part I. Cyclization of benzylsulphonamides
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Orazi,Corral,Bravo
p. 1701 - 1708
(2007/10/02)

Organic compounds substituted heptadeca-5,9- and 5,10-dienoic acid
The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.
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(2008/06/13)