Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase

Benfodda, Zohra; Guillen, F.; Romestand, Bernard; Dahmani, Abdelkader; Blancou, H.

doi:10.1016/j.ejmech.2009.11.052

Cited by 18 publications

(12 citation statements)

References 17 publications

(18 reference statements)

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“…In this context, -alkyl or -alkenyl ,-difluorinated sulfonamides have recently drawn much attention, since the introduction of two fluorine atoms into the carbon atom  to the sulfonamide functionality results in a decrease of the basicity of sulfonamide as well as an increase of lipophilicity [13]. Both of these features have important impacts on biological activity [13][14][15][16]. However, the synthetic methods for the efficient preparation of -alkyl or -alkenyl ,-difluorinated sulfonamides are scarce, except for the two major methods being the electrophilic fluorination [13,17,18] and nucleophilic fluoroalkylation [19].…”

Section: Introductionmentioning

confidence: 98%

Free radical fluoroalkylation of terminal alkenes and alkynes with iododifluoromethanesulfonamides

Zhu

Wang

2011

Sci. China Chem.

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Section: Introductionmentioning

confidence: 98%

Free radical fluoroalkylation of terminal alkenes and alkynes with iododifluoromethanesulfonamides

Zhu

Wang

2011

Sci. China Chem.

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“…Various alcohols (12a and 12p-t) 30,31) were alkylated by methyl 4-(bromomethyl) benzoate 13 with NaH or Ag 2 O, and then hydrolyzed with aqueous LiOH or NaOH to afford the carboxylic acids 14a, and 14p-t. Compounds 14a and 14p-t underwent condensation with sulfonamides 2A-D, and 2F-I [32][33][34] to give 15aA, 15pA-tA, 15rB, 15rC, and 15rF-rH. The methyl ester of 15rD was hydrolyzed with aqueous LiOH to afford 15rE.…”

Section: Chemistrymentioning

confidence: 99%

“…Separately, compound 16 was hydrolyzed and alkylated with 1-bromo-4-bromomethylbenzene in the presence of sodium methoxide, and then acylated with diethyl oxalate to give 20. Compound 20 was hydrolyzed and underwent condensation with sulfonamide 2K 34) to give 22. Compound 19 was synthesized from compound 17 by the Curtius rearrangement, deprotection of the Boc group with trifluoroacetic acid (TFA), and acylation with ethyl chloroglyoxylate.…”

Section: Chemistrymentioning

confidence: 99%

Novel Non-carboxylate Benzoylsulfonamide-Based Protein Tyrosine Phosphatase 1B Inhibitors with Non-competitive Actions

Morishita

Shoji

Tanaka

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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A novel series of benzoylsulfonamide derivatives were synthesized and biologically evaluated. Among them, 4-(biphenyl-4-ylmethylsulfanylmethyl)-N-(hexane-1-sulfonyl)benzamide (compound 18K) was identified as a protein tyrosine phosphatase 1B (PTP1B) inhibitor with potent and selective inhibitory activity against PTP1B (IC 50 0.25 µM). Compound 18K functioned as a non-competitive inhibitor and bound to the allosteric site of PTP1B. It also showed high oral absorption in mice (the maximum drug concentration (C max ) 45.5 µM at 30 mg/kg), rats (C max 53.6 µM at 30 mg/kg), and beagles (C max 37.8 µM at 10 mg/kg), and significantly reduced plasma glucose levels at 30 mg/kg/d (per os (p.o.)) for one week with no side effects in db/db mice. In conclusion, the substituted benzoylsulfonamide was shown to be a novel scaffold of a noncompetitive and allosteric PTP1B inhibitor, and compound 18K has potential as an efficacious and safe antidiabetic drug as well as a useful tool for investigations of the physiological and pathophysiological effects of allosteric PTP1B inhibition.Key words benzoylsulfonamide; protein tyrosine phosphatase 1B; allosteric inhibitor; non-competitive inhibitor; db/db mouse; Sprague-Dawley rat In various cellular signaling pathways, protein tyrosine kinases (PTKs) mediate the phosphorylation of tyrosine residues in a number of proteins, while protein tyrosine phosphatases (PTPs) de-phosphorylate phosphorylated tyrosine.

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“…Sulfonamides have been demonstrated to possess antibacterial, [1][2][3][4] antifungal, 5 insulin releasing, [6][7][8] carbonic anhydrase inhibitory, [9][10][11][12] hypoglycemic, 13 anesthetic, 14 anti-tumor, 15,16 anti-cancer and anti-inflammatory [17][18][19] activities. Some active sulfonamides as anti-bacterial are also known for their immune modifying effects.…”

Section: Introductionmentioning

confidence: 99%

HETEROAROMATIZATION WITH SULFONAMIDO PHENYL ETHANONE: PART (IV). SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW N-ETHYL-N-METHYLBENZENESULFONAMIDE, 1,3,4-THIADIAZOLE, 1,3,4-THIADIAZINE, 4-OXOTHIAZOLIDINE AND PYRAZOLO[5,1-c][1,2,4]TRIAZINE DERIVATIVES

Abdelall

Bashandy

El_Morsy

2010

Al-Azhar Bulletin of Science

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This article describes the synthesis of some novel sulfonamide having the biologically active, hydrazones 7-11, 1,3,4-thiadiazoles 15-18, 20, 1,3,4-thiadiazine 19, 4-oxothiazolidines 21, 26-29 and pyrazolo[5,1-c][1,2,4]triazine 32 moieties starting with 4-acetyl-N-ethyl-Nmethylbenzenesulfonamide (1). The structure of the newly synthesized compounds was confirmed by elemental analysis, IR, 1 H NMR, and mass spectral data.

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Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase

Cited by 18 publications

References 17 publications

Free radical fluoroalkylation of terminal alkenes and alkynes with iododifluoromethanesulfonamides

Free radical fluoroalkylation of terminal alkenes and alkynes with iododifluoromethanesulfonamides

Novel Non-carboxylate Benzoylsulfonamide-Based Protein Tyrosine Phosphatase 1B Inhibitors with Non-competitive Actions

HETEROAROMATIZATION WITH SULFONAMIDO PHENYL ETHANONE: PART (IV). SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW N-ETHYL-N-METHYLBENZENESULFONAMIDE, 1,3,4-THIADIAZOLE, 1,3,4-THIADIAZINE, 4-OXOTHIAZOLIDINE AND PYRAZOLO[5,1-c][1,2,4]TRIAZINE DERIVATIVES

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