cas 2645-02-5, Methyl 2-(4-methylphenylsulfonamido)acetate

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A practical method for N-cyanation of secondary amines and sulfonamides
Cyanamides are an important class of molecules. This work describes a facile synthesis of disubstituted cyanamides. Here, readily accessible 1-cyano-1, 2-benziodoxol-3-(1H)-one (CBX) was applied as a stable electrophilic cyanation reagent. Diverse secondary amines were effectively cyanated. Moreover, secondary sulfonamides proved to be suitable substrates and were readily converted to N-alkyl(aryl)-N-arylsulfonyl-cyanamides, as the significant building blocks of the organic transformation.
Hang, Zhaojun,Tong, Xiaowei,Li, Zuowa,Wang, Zhao-yan,Xue, Weihua
supporting information

(2022/02/07)

Nitroxyl Catalysts for Six-Membered Ring Bromolactonization and Intermolecular Bromoesterification of Alkenes with Carboxylic Acids
We developed a nitroxyl-catalyzed bromoesterification of alkenes with bromo reagents, which includes a six-membered ring bromolactonization of alkenyl carboxylic acids catalyzed by AZADO as the nitroxyl radical catalyst, and an intermolecular bromoesterification of alkenes with carboxylic acids using NMO as the N-oxide catalyst. We also accomplished a remote diastereoselective bromohydroxylation via an AZADO-catalyzed six-membered ring bromolactonization and a subsequent ring cleavage reaction with alkylamines to furnish ?-bromo-δ-hydroxy amides with high diastereoselectivity.
Moriyama, Katsuhiko,Kuramochi, Masako,Tsuzuki, Seiji,Fujii, Kozo,Morita, Takeshi
supporting information
p. 268 - 273
(2021/01/09)

Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications
Herein we report a catalyst- and metal-free visible-light-mediated protocol enabling the iodoamination of miscellaneous olefins. This protocol is characterized by high yields under environmentally benign reaction conditions utilizing commercially available substrates and a green and biodegradable solvent. Furthermore, the protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, which offers manifold possibilities for further transformations, including morpholine, piperidine, pyrrolidine, and aziridine synthesis.
Engl, Sebastian,Reiser, Oliver
supporting information
p. 5581 - 5586
(2021/07/26)

ANTIVIRAL 1,3-DI-OXO-INDENE COMPOUNDS
The invention provides compounds of Formula (I): as described herein, along with pharmaceutically acceptable salts, pharmaceutical compositions containing such compounds, and methods to use these compounds, salts and compositions for treating viral infections.
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Paragraph 0278

(2021/10/22)

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite
In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.
Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao
supporting information
p. 2713 - 2718
(2021/06/25)

Synthesis and Formation Mechanism of a Compound with an Unprecedented Skeleton: Dodecahydro-4,10:5,9-diepoxydipyrrolo[3,4-b:3′,4′-f][1,5]diazocine
The reaction of N-(2-{[(tert-butyldimethylsilyl)oxy]imino}ethyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)benzenesulfonamide (6b) with BF3·OEt2 afforded a compound with an unprecedented dodeca-hydro-4,10:5,9-diepoxydipyrrolo[3,4-b:3′,4′-f]
Shinoda, Misaki,Morita, Nobuyoshi,Tanaka, Kosaku,Hashimoto, Yoshimitsu,Ban, Shintaro,Tamura, Osamu
p. 1238 - 1243
(2020/12/18)

Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles
Functionalization at the α-position of carbonyl compounds has classically relied on enolate chemistry. As a result, the generation of a new C-X bond, where X is more electronegative than carbon requires an oxidation event. Herein we show that, by rendering the α-position of amides electrophilic through a mild and chemoselective umpolung transformation, a broad range of widely available oxygen, nitrogen, sulfur, and halogen nucleophiles can be used to generate α-functionalized amides. More than 60 examples are presented to establish the generality of this process, and calculations of the mechanistic aspects underline a fragmentation pathway that accounts for the broadness of this methodology.
Gon?alves, Carlos R.,Lemmerer, Miran,Teskey, Christopher J.,Adler, Pauline,Kaiser, Daniel,Maryasin, Boris,González, Leticia,Maulide, Nuno
supporting information
p. 18437 - 18443
(2019/11/21)

Synthesis of Indolizine and Pyrrolo[1,2- a]azepine Derivatives via a Gold(I)-Catalyzed Three-Step Cascade
Linear N-alkenyl or alkynyl N-sulfonyl 1-aminobut-3-yn-2-ones are converted into bicyclic indolizines and pyrrolo[1,2-a]azepine-type alkaloids upon gold(I) catalysis (17 examples, 10-85%). The reaction cascade allowed formation of C-N, O-S, and C-C bonds via a cycloisomerization/sulfonyl migration/cyclization process using 10 mol % of [(2-biphenyl)di-tert-butylphosphine]gold(I) triflimide complex in dichloromethane.
Sirindil, Fatih,Golling, Stéphane,Lamare, Rapha?l,Weibel, Jean-Marc,Pale, Patrick,Blanc, Aurélien
supporting information
p. 8997 - 9000
(2019/11/11)

Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex
The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.
Yudasaka, Masaharu,Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika
p. 1098 - 1102
(2019/05/16)

Sulfonyl Azides as Precursors in Ligand-Free Palladium-Catalyzed Synthesis of Sulfonyl Carbamates and Sulfonyl Ureas and Synthesis of Sulfonamides
(Chemical Equation Presented). An efficient synthesis of sulfonyl carbamates and sulfonyl ureas from sulfonyl azides employing a palladium-catalyzed carbonylation protocol has been developed. Using a two-chamber system, sulfonyl azides, PdCl2, and CO gas, released ex situ from Mo(CO)6, were assembled to generate sulfonyl isocyanates in situ, and alcohols and aryl amines were exploited as nucleophiles to afford a broad range of sulfonyl carbamates and sulfonyl ureas. A protocol for the direct formation of substituted sulfonamides from sulfonyl azides and amines via nucleophilic substitution was also developed.
Chow, Shiao Y.,Stevens, Marc Y.,Odell, Luke R.
p. 2681 - 2691
(2016/04/26)

Identification of bidentate salicylic acid inhibitors of PTP1B
PTP1B is a master regulator in the insulin and leptin metabolic pathways. Hyper-activated PTP1B results in insulin resistance and is viewed as a key factor in the onset of type II diabetes and obesity. Moreover, inhibition of PTP1B expression in cancer cells dramatically inhibits cell growth in vitro and in vivo. Herein, we report the computationally guided optimization of a salicylic acid-based PTP1B inhibitor 6, identifying new and more potent bidentate PTP1B inhibitors, such as 20h, which exhibited a > 4-fold improvement in activity. In CHO-IR cells, 20f, 20h, and 20j suppressed PTP1B activity and restored insulin receptor phosphorylation levels. Notably, 20f, which displayed a 5-fold selectivity for PTP1B over the closely related PTPσ protein, showed no inhibition of PTP-LAR, PRL2 A/S, MKPX, or papain. Finally, 20i and 20j displayed nanomolar inhibition of PTPσ, representing interesting lead compounds for further investigation.
Haftchenary, Sina,Jouk, Andriana O.,Aubry, Isabelle,Lewis, Andrew M.,Landry, Melissa,Ball, Daniel P.,Shouksmith, Andrew E.,Collins, Catherine V.,Tremblay, Michel L.,Gunning, Patrick T.
supporting information
p. 982 - 986
(2015/09/22)

Carbonic anhydrase inhibitors: Design, synthesis, kinetic, docking and molecular dynamics analysis of novel glycine and phenylalanine sulfonamide derivatives
The inhibition of two human cytosolic carbonic anhydrase isozymes I and II, with some novel glycine and phenylalanine sulfonamide derivatives were investigated. Newly synthesized compounds G1-4 and P1-4 showed effective inhibition profiles with KI values in the range of 14.66-315 μM for hCA I and of 18.31-143.8 μM against hCA II, respectively. In order to investigate the binding mechanisms of these inhibitors, in silico docking studies were applied. Atomistic molecular dynamic simulations were performed for docking poses which utilize to illustrate the inhibition mechanism of used inhibitors into active site of CAII. These sulfonamide containing compounds generally were competitive inhibitors with 4-nitrophenylacetate as substrate. Some investigated compounds here showed effective hCA II inhibitory effects, in the same range as the clinically used sulfonamide, sulfanilamide or mafenide and might be used as leads for generating enzyme inhibitors possibly targeting other CA isoforms which have not been yet assayed for their interactions with such agents.
Fidan, Ismail,Salmas, Ramin Ekhteiari,Arslan, Mehmet,?entürk, Murat,Durdagi, Serdar,Ekinci, Deniz,?entürk, Esra,Co?gun, Sedat,Supuran, Claudiu T.
p. 7353 - 7358
(2015/11/27)

Inhibiting aberrant signal transducer and activator of transcription protein activation with tetrapodal, small molecule Src homology 2 domain binders: Promising agents against multiple myeloma
The signal transducer and activator of transcription (STAT) proteins represent a family of cytoplasmic transcription factors that regulate a pleiotropic range of biological processes. In particular, Stat3 protein has attracted attention as it regulates the expression of genes involved in a variety of malignant processes, including proliferation, survival, migration, and drug resistance. Multiple myeloma (MM) is an incurable hematologic malignancy that often exhibits abnormally high levels of Stat3 activity. Although current treatment strategies can improve the clinical management of MM, it remains uniformly incurable with a dismal median survival time post-treatment of 3-4 years. Thus, novel targeted therapeutics are critically needed to improve MM patient outcomes. We herein report the development of a series of small molecule Stat3 inhibitors with potent anti-MM activity in vitro. These compounds showed high-affinity binding to Stat3's SH2 domain, inhibited intracellular Stat3 phosphorylation, and induced apoptosis in MM cell lines at low micromolar concentrations.
Page, Brent D. G.,Croucher, Danielle C.,Li, Zhi Hua,Haftchenary, Sina,Jimenez-Zepeda, Victor H.,Atkinson, Jennifer,Spagnuolo, Paul A.,Wong, Yoong Lim,Colaguori, Robert,Lewis, Andrew M.,Schimmer, Aaron D.,Trudel, Suzanne,Gunning, Patrick T.
supporting information
p. 7190 - 7200
(2013/10/21)

Sulfonamide synthesis via oxyma-O-sulfonates - Compatibility to acid sensitive groups and solid-phase peptide synthesis
A milder and more efficient procedure for the synthesis of sulfonamides by activating sulfonic acid groups as the corresponding sulfonate esters of ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) is reported. This method is greener than all other existing protocols for the purpose. Other important advantages lie in (a) its applicability to less nucleophilic anilines under ambient and milder conditions and (b) its compatibility with solid phase peptide synthesis and acid-labile groups such as trityl (Trt) and tBu, which empowers the solid phase synthesis of sulfonamides of various peptides. To illustrate this, the syntheses of three sulfonamide derivatives of the peptide GAILG-NH2, which is relevant in the context of drug design against type 2 diabetes, are demonstrated by using Fmoc-based solid-phase peptide synthesis (SPPS). The activation of sulfonic acids as their corresponding O-sulfonate esters facilitates sulfonamide synthesis, which can be applied to those substrates that possess acid-labile functional groups and is compatible with solid phase synthesis. Copyright
Palakurthy, Nani Babu,Dev, Dharm,Rana, Shubhasmin,Nadimpally, Krishna Chaitanya,Mandal, Bhubaneswar
p. 2627 - 2633
(2013/06/04)

Antagonism of the Stat3-Stat3 Protein Dimer with Salicylic Acid Based Small Molecules
More than 50 new inhibitors of the oncogenic Stat3 protein were identified through a structure-activity relationship (SAR) study based on the previously identified inhibitor S3I-201 (IC50=86μM, Ki>300μM). A key structural feature of
Fletcher, Steven,Page, Brent D.G.,Zhang, Xialoei,Yue, Peibin,Li, Zhi Hua,Sharmeen, Sumaiya,Singh, Jagdeep,Zhao, Wei,Schimmer, Aaron D.,Trudel, Suzanne,Turkson, James,Gunning, Patrick T.
scheme or table
p. 1459 - 1470
(2012/07/01)

Synthesis and Antiviral Evaluation of New N-acylhydrazones Containing Glycine Residue
N-acylhydrazones containing glycine residue 3a-j and 8a-h were synthesized as HIV-1 capsid protein assembly inhibitors. The structures of the novel N-acylhydrazone derivatives were characterized using different spectroscopic methods. Antiviral activity de
Tian, Baohe,He, Meizi,Tan, Zhiwu,Tang, Shixing,Hewlett, Indira,Chen, Shuguang,Jin, Yinxue,Yang, Ming
experimental part
p. 189 - 198
(2012/02/01)

Sulfonamide synthesis using N-hydroxybenzotriazole sulfonate: An alternative to pentafluorophenyl (PFP) and trichlorophenyl (TCP) esters of sulfonic acids
The N-hydroxybenzotriazole (HOBt) sulfonate esters undergo amidation under ambient conditions in the presence of di-isopropylethyl amine. This method can be applied to varieties of amines including sterically hindered amino acid esters in less time with reasonably good yields. HOBt ester of sulfonic acids can be a replacement for pentafluorophenyl and trichlorophenyl ester as well as chloride moiety of sulfonyl chloride for amidation.
Palakurthy, Nani Babu,Mandal, Bhubaneswar
supporting information; experimental part
p. 7132 - 7134
(2012/02/01)

Chemoselective esterification and amidation of carboxylic acids with imidazole carbamates and ureas
Imidazole carbamates and ureas were found to be chemoselective esterification and amidation reagents. A wide variety of carboxylic acids were converted to their ester or amide analogues by a simple synthetic procedure in high yields.
Heller, Stephen T.,Sarpong, Richmond
supporting information; experimental part
p. 4572 - 4575
(2010/12/25)

DABCO-Catalyzed 1,4-bromolactonization of conjugated enynes: Highly stereoselective formation of a stereogenic center and an axially chiral allene
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Zhang, Wen,Xu, Huadong,Xu, Hui,Tang, Weiping
supporting information; experimental part
p. 3832 - 3833
(2009/08/08)

Synthesis and antiviral activities of novel acylhydrazone derivatives targeting HIV-1 capsid protein
HIV-1 capsid protein (CA) plays important roles in the viral replication cycle. A number of acylhydrazone derivatives that act as inhibitors of HIV-1 CA assembly, were designed and synthesized. The synthesized compounds were tested for their antiviral activities and cytotoxicities using CEM cells. Some derivatives also were assayed for their ability to inhibit HIV-1 CA assembly in vitro. Among them, compounds 14f and 14i display the most promising potency with EC50 values of 0.21 and 0.17 μΜ, respectively.
Tian, Baohe,He, Meizi,Tang, Shixing,Hewlett, Indira,Tan, Zhiwu,Li, Jiebo,Jin, Yinxue,Yang, Ming
scheme or table
p. 2162 - 2167
(2009/12/25)

SmI2-promoted intra- and intermolecular C-C bond formation with chiral N-acyl oxazolidinones
The suitability of chiral oxazolidinones in the SmI2-mediated C-C bond generation between the imide functionality of an N-acyl oxazolidinone unit and an olefinic radical acceptor, in both inter- and intramolecular reactions, was investigated. It was shown that the products from an Evans asymmetric alkylation can undergo direct carbon-carbon bond formation with an acrylamide providing chiral acyclic ketones in reasonable yields. These examples represent the first transformation of such N-acyl oxazolidinones where this chiral auxiliary is removed under the conditions for ketone formation. 5-exo-trig Cyclization studies were also undertaken with the same type of substrates, providing trans-2,5-disubstituted cyclopentanones in yields of approx. 50%. However, attempts to cyclize heteroatom-containing equivalents were less rewarding.
Taaning, Rolf H.,Thim, Laura,Karaffa, Jacob,Campa?a, Araceli G.,Hansen, Anna-Mette,Skrydstrup, Troels
experimental part
p. 11884 - 11895
(2009/04/07)

PHENYL-3-{ (3- (1H- PYRROL- 2 -YL) - [1 , 2 , 4] 0XADIAZ0L-5-YL] PIPERIDIN-1-YL}-METHANONE DERIVATIVES AND RELATED COMPOUNDS AS POSITIVE ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
The present invention provides new compounds of formula (I) as positive allosteric modulators of metabotropic receptors - subtype 5 ("mGluR5") which are useful for the treatment or prevention of central nervous system disorders such as for example, cognitive decline, both positive and negative symptoms in schizophrenia as well as other central or peripheral nervous system disorders in which the mGluR5 subtype of glutamate metabotropic receptor is involved. The invention is also directed to pharmaceutical compounds and compositions in the prevention or treatment of such diseases in which mGluKi is involved. W represents (C4-C7)cycloalkyl, (C3-C7)heterocycloalkyl , (C3-C7)heterocycloalkyl-(C1-C3)alkyl or (C3-C7)heterocycloalkenyl ring; represents a (C5-C7)heteroeycloalkyl, (C5-C7)heterocycloalkeiiyl ring or a heteroaryl group of formula (a), (b), (c), (d), (e), (f), (g), (i). Q denotes a cycloalkyl, an aryl or heteroaryl group of formula (j), (k), (l), (m), (n). A is azo -N=N-, ethyl, ethenyl, ethynyl, -NR8C(=O)-, -NR8C(=O)-O-, -NR8C(=O)-NR9, NR8S(=O)2-, -C(=O)NR8-, -O-C(=O)NR8-, -S-, -S(=O)-, -S(=O)2-, -S(C=O)2NR8-, -C(=0)-0-, -0-C(=0)-, -C(=NR8)NR9-, C(C=NOR8)NR9- , -NR8C(=NOR9)-, =N-0-, -0-N=CH- or a group aryl or heteroaryl of formula, (o), (p), (q), (r), (s), (t), (u), (v), (w), (x). The other substituents are defined in the claims.
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Page/Page column 77

(2008/06/13)

Aerobic oxidative cyclization under Pd(II) catalysis: A regioselective approach to heterocycles
(Chemical Equation Presented) An efficient Yb(OTf)3-promoted palladium-catalyzed oxidative cyclization of γ-heteroalkenyl β-keto amides has been developed. Under simple aerobic condition, a variety of six-, seven-, and eight-membered-ring N- an
Yip, Kai-Tai,Li, Jin-Heng,Lee, On-Yi,Yang, Dan
p. 5717 - 5719
(2007/10/03)

Unexpected alkoxyl migration in the reaction of silyl ketene acetals with p-toluenesulfonyl azide
The reaction of p-toluenesulfonyl azides with several silyl ketene acetals has been investigated. 1-Trimethylsilyloxy-ethylene reacted with TsN3 to give a good yield of N-p-toluenesulfonyl substituted glycinates exclusively. However, during the reaction of 1-trimethylsilyloxy-propene with TsN3, an unexpected alkoxyl migration occurred to give N-acylsulfonyl amides; other products, N-p-toluenesulfonyl substituted aziridines were also obtained. In the case of dialkyl substituted silyl ketene acetals, three products were formed, i.e. aziridines, α-amino esters, and N-acylsulfonyl amides. The mechanism for the alkoxyl migration was discussed.
Xu, Yong,Zhu, Shizheng
p. 3909 - 3913
(2007/10/03)

Synthesis of N-Protected Amino Esters via Palladium Catalysed Allylic Substitution
N-protected allylamines were prepared by palladium catalysed allylic substitution of the corresponding allyl acetates with a range of nitrogen nucleophiles.The so-formed N-protected allylamines were subjected to oxidative cleavage of the alkene to afford N-protected amino acids or esters.
Jumnah, Roshan,Williams, Jonathan M. J.,Williams, Andrew C.
p. 6619 - 6622
(2007/10/02)

An Improved Synthesis of Pyrroles from N-p-Toluenesulfonylglycine Esters and α,β-Unsaturated Aldehydes and Ketones
N-p-Toluenesulfonylglycine esters 2 condensed with α,β-unsaturated carbonyl compounds 1 in the presence of the non-nucleophilic base DBU to give hydroxypyrrolidines 3.Dehydration with phosphorous oxychloride-pyridine, followed by DBU mediated elimination
Lash, Timothy D.,Hoehner, Michael C.
p. 1671 - 1676
(2007/10/02)

BENZOPHENANTHRIDINES. VIII. SYNTHESIS AND STRUCTURE OF cis-2-METHOXY-5-TOSYL-4b,5,6,10b,11,12-HEXAHYDROBENZOPHENANTHRIDINE
The total synthesis of cis-2-methoxy-5-tosyl-4b,5,6,10b,11,12-hexahydrobenzophenathridine was realized from the hydrochloride of methyl aminoacetate by successive ring growth AB->ABD->ABDC in five stages, including the addition of 3-methoxyphenylmagnes
Rozhkov, V. S.,Sladkov, V. I.,Turdybekov, K. M.,Lindeman, S. V.,Kolesnikov, A. Yu.,et al.
p. 1162 - 1167
(2007/10/02)

INDIRECT ELECTROCHEMICAL α-METHOXYLATION OF N-ACYL AND N-CARBOALKOXY α-AMINO ACID ESTERS AND APPLICATION AS CATIONIC GLYCINE EQUIVALENTS
Indirect electrochemical methoxylation of N-acyl and N-carboalkoxy α-amino acid esters in α-position to nitrogen is possible, if chloride is used as mediator.The course of the reaction depends upon the protecting group as well as upon the amino acid side-chain.Increased electron withdrawing effects of the protecting group are accelerating the reaction.On the other hand aliphatic side-chains are diminishing the reactivity.High chloride ion concentrations improve the current yields surprisingly strong.
Ginzel, Klaus-Dieter,Brungs, Peter,Steckhan, Eberhard
p. 1691 - 1702
(2007/10/02)

SYNTHESE DE DERIVES DIAMIDIQUES N-PHOSPHORYLES D'AMINOACIDES
Twenty seven phosphordiamides incorporating one (3,3') or two (5) α aminoester residues and seven aminoamide phosphodiesters (6) were synthetised starting generally from the corresponding tetrahedral phosphorus chlorides 1 and 7, respectively.
Mulliez, M.
p. 209 - 220
(2007/10/02)