- Fe-exchanged montmorillonite K10 - The first heterogeneous catalyst for acylation of sulfonamides with carboxylic acid anhydrides
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Fe-exchanged montmorillonite K10 catalyzes a highly efficient reaction between sterically and electronically diverse sulfonamides and carboxylic acid anhydrides to furnish N-acylsulfonamides in excellent yield and high selectivity. The catalyst can also be reused several times.
- Singh, Devendrapratap U.,Singh, Pankajkumar R.,Samant, Shriniwas D.
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- Solvent effects on the solvolyses of N-benzoyl-arenesulfonimidoyl chlorides
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Rates of solvolyses of N-benzoyl-arenesulfonimidoyl chlorides have been studied in different compositions of aqueous organic solvents and analysed in terms of the mol fraction of organic solvent, the dielectric constant, the Kirkwood function, the polarisibility, some ENT values, a multiparameter equation and the Grunwald-Winstein equation. All these criteria were consistent with a concerted bimolecular SN2 mechanism of solvolysis.
- Kutuk, Halil,Tillett, John G.
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- N-Sulfonyl acetylketenimine as a highly reactive intermediate for synthesis of N-Aroylsulfonamides
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A highly reactive intermediate N-sulfonyl acetylketenimine was generated from an ynone-participated CuAAC/ring-opening method. Its unique structure allowed it to react with aryl carboxylic acids to give N-aroylsulfonamides via a novel Mumm-type rearrangement.
- Yang, Weiguang,Huang, Dayun,Zeng, Xiaobao,Zhang, Jianlan,Wang, Xinyan,Hu, Yuefei
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p. 381 - 386
(2018/12/13)
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- Catalytic activity of magnetic Fe3O4@Diatomite earth and acetic acid for the N-acylation of sulfonamides
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The Br?nsted and Lewis acidic promoted N-acylation of sulfonamides with acetic anhydride or benzoyl chloride has been achieved using glacial acetic acid and magnetic Fe3O4@Diatomite earth. Use of acetic acid as solvent omits the need for organic bases and permits the isolation of products by filtration and precipitation. Additionally, the magnetic composite Fe3O4@Diatomite acts as a conjugate proton super acid, enabling the acylation of sulfonamide compounds.
- Ghasemi, Mohammad Hadi,Kowsari, Elaheh,Hosseini, Seyed Kiumars
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supporting information
p. 387 - 391
(2016/01/12)
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- Development of an acyl sulfonamide anti-proliferative agent, ly573636 ? na
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The synthesis of 5-bromo-thiophene-2-sulfonic acid 2,4-dichlo- robenzoylamide sodium salt on multikilogram scale is described. The initial clinical supplies were made using carbonyl diimidazole to converge the two fragments. A more efficient acid chloride process has been developed, which also provides better control of impurities and color throughout the synthesis.
- Yates, Matthew H.,Kallman, Neil J.,Ley, Christopher P.,Wei, Jeffrey N.
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experimental part
p. 255 - 262
(2010/04/22)
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- β-Keto sulfones as inhibitors of 11β-hydroxysteroid dehydrogenase type I and the mechanism of action
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The design, synthesis, and biological evaluation of β-keto sulfones as 11β-HSD1 inhibitors and the mechanism of inhibition are described here. This class of compounds is not active against 11β-HSD2 and therefore may have therapeutic potential for metabolic syndrome and type 2 diabetes.
- Xiang, Jason,Ipek, Manus,Suri, Vipin,Tam, May,Xing, Yuzhe,Huang, Nelson,Zhang, Yanling,Tobin, James,Mansour, Tarek S.,McKew, John
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p. 4396 - 4405
(2008/03/12)
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- An expeditious and convenient synthesis of acylsulfonamides utilizing polymer-supported reagents
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Acylsulfonamides can be rapidly and conveniently synthesized from a variety of carboxylic acids and sulfonamides utilizing the commercially available reagents, PS-DCC and DMAP under mild reaction conditions. DMAP can be efficiently scavenged by utilizatio
- Wang, Ying,Sarris, Kathy,Sauer, Daryl R.,Djuric, Stevan W.
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p. 5181 - 5184
(2008/02/08)
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- Acyl sulfonamide anti-proliferatives: Benzene substituent structure-activity relationships for a novel class of antitumor agents
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Two closely related diaryl acylsulfonamides were recently reported as potent antitumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary, and prostate) in nude mice. Especially intriguing was their activity against colorectal cancer xenografts. In this paper, rapid parallel synthesis along with traditional medicinal chemistry techniques were used to quickly delineate the structure-activity relationships of the substitution patterns in both phenyl rings of the acylsufonamide anti-proliferative scaffold. Although the molecular target of the compounds remains unclear, we determined that the vascular endothelial growth factor-dependent human umbilical vein endothelial cells assay in combination with a soft agar disk diffusion assay allowed for optimization of potency in the series. The pharmacokinetic properties and in vivo activity in an HCT116 xenograft model are reported for representative compounds.
- Lobb, Karen L.,Hipskind, Philip A.,Aikins, James A.,Alvarez, Enrique,Cheung, Yiu-Yin,Considine, Eileen L.,De Dios, Alfonso,Durst, Gregory L.,Ferritto, Rafael,Grossman, Cora Sue,Giera, Deborah D.,Hollister, Beth A.,Huang, Zhongping,Iversen, Philip W.,Law, Kevin L.,Li, Tiechao,Lin, Ho-Shen,Lopez, Beatriz,Lopez, Jose E.,Martin Cabrejas, Luisa M.,McCann, Denis J.,Molero, Victoriano,Reilly, John E.,Richett, Michael E.,Shih, Chuan,Teicher, Beverly,Wikel, James H.,White, Wesley T.,Mader, Mary M.
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p. 5367 - 5380
(2007/10/03)
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- A convenient method for the preparation of acylsulfonamide libraries
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The preparation of an acylsulfonamide library is described using resin bound EDC (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide). A polymer supported sulfonic acid (A-15) is used as a scavenger to remove dimethylaminopyridine and purification only involve
- Sturino, Claudio F.,Labelle, Marc
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p. 5891 - 5894
(2007/10/03)
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- A STUDY OF TRANSMISSION EFFECTS OF SULFONYL AND CARBONYL GROUPS
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Seventeen p-substituted N-phenylsulfonylbenzamides of general formulas XC6H4SO2NHCOC6H5 and C6H5SO2NHCOC6H4X have been synthesized and their structure has been confirmed by elemental analysis and 1H NMR spectra.The dissociation constants of all compounds have been measured by potentiometric titration in methanol, acetonitrile, dimethylformamide, dimethyl sulfoxide, and pyridine.The obtained pKHA values have been correlated with three sets of Hammett substituent constants using simple or double linear regression.The solvent and substituent effects are discussed on the basis of experimental results, and the difference between the substituent effects from sulfonamide and benzamide sections is evaluated.It has been found that due to extensive delocalization of negative charge in the conjugated base the transmission effects of carbonyl and sulfonyl groups on the transmission of substituent effect are roughly the same.The experimental data have been interpreted by the methods with latent variables: the principal component analysis (PCA), the conjugated deviation analysis (CDA), and the method of projection to latent structures (PLS).The results obtained by these procedures were similar.
- Ludwig, Miroslav,Parik, Patrik,Kulhanek, Jiri
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p. 841 - 850
(2007/10/02)
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