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Anticonvulsant 4-aminobenzenesulfonamide derivatives with branched-alkylamide moieties: X-ray crystallography and inhibition studies of human carbonic anhydrase isoforms I, II, VII, and XIV.

Hen N, Bialer M, Yagen B, Maresca A, Aggarwal M, Robbins AH, McKenna R, Scozzafava A, Supuran CT
J Med Chem 54 3977-81 (2011)
Related entries: 3oy0, 3oyq

Cited: 36 times
EuropePMC logo PMID: 21506569

Abstract

Aromatic amides comprising branched aliphatic carboxylic acids and 4-aminobenzenesulfonamide were evaluated for their inhibition of carbonic anhydrase (CA) isoforms. Of the most anticonvulsant-active compounds (2, 4, 13, 16, and 17), only 13, 16, and 17 were potent inhibitors of CAs VII and XIV. Compounds 9, 14, and 19 inhibited CA II, while 10 and 12 inhibited all isoforms. Structural studies suggest that differences in the active sites' hydrophobicity modulate the affinity of the inhibitors.

Articles - 3oys mentioned but not cited (2)

  1. Insights towards sulfonamide drug specificity in α-carbonic anhydrases. Aggarwal M, Kondeti B, McKenna R. Bioorg. Med. Chem. 21 1526-1533 (2013)
  2. Structural study of the location of the phenyl tail of benzene sulfonamides and the effect on human carbonic anhydrase inhibition. Güzel-Akdemir O, Biswas S, Lastra K, McKenna R, Supuran CT. Bioorg. Med. Chem. 21 6674-6680 (2013)


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  1. Structure-based drug discovery of carbonic anhydrase inhibitors. Supuran CT. J Enzyme Inhib Med Chem 27 759-772 (2012)
  2. How many carbonic anhydrase inhibition mechanisms exist? Supuran CT. J Enzyme Inhib Med Chem 31 345-360 (2016)
  3. Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. De Simone G, Alterio V, Supuran CT. Expert Opin Drug Discov 8 793-810 (2013)
  4. Update on carbonic anhydrase inhibitors: a patent review (2008 - 2011). Aggarwal M, McKenna R. Expert Opin Ther Pat 22 903-915 (2012)
  5. Reconsidering anion inhibitors in the general context of drug design studies of modulators of activity of the classical enzyme carbonic anhydrase. Nocentini A, Angeli A, Carta F, Winum JY, Zalubovskis R, Carradori S, Capasso C, Donald WA, Supuran CT. J Enzyme Inhib Med Chem 36 561-580 (2021)
  6. Insights into Potential Targets for Therapeutic Intervention in Epilepsy. Zavala-Tecuapetla C, Cuellar-Herrera M, Luna-Munguia H. Int J Mol Sci 21 E8573 (2020)
  7. Thermodynamic, kinetic, and structural parameterization of human carbonic anhydrase interactions toward enhanced inhibitor design. Linkuvienė V, Zubrienė A, Manakova E, Petrauskas V, Baranauskienė L, Zakšauskas A, Smirnov A, Gražulis S, Ladbury JE, Matulis D. Q Rev Biophys 51 e10 (2018)
  8. Emerging trends in environmental and industrial applications of marine carbonic anhydrase: a review. Iraninasab S, Sharifian S, Homaei A, Homaee MB, Sharma T, Nadda AK, Kennedy JF, Bilal M, Iqbal HMN. Bioprocess Biosyst Eng 45 431-451 (2022)

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  2. A class of sulfonamide carbonic anhydrase inhibitors with neuropathic pain modulating effects. Carta F, Di Cesare Mannelli L, Pinard M, Ghelardini C, Scozzafava A, McKenna R, Supuran CT. Bioorg. Med. Chem. 23 1828-1840 (2015)
  3. Combining the tail and the ring approaches for obtaining potent and isoform-selective carbonic anhydrase inhibitors: solution and X-ray crystallographic studies. Bozdag M, Ferraroni M, Nuti E, Vullo D, Rossello A, Carta F, Scozzafava A, Supuran CT. Bioorg. Med. Chem. 22 334-340 (2014)
  4. Carbonic anhydrase inhibitors: benzenesulfonamides incorporating cyanoacrylamide moieties are low nanomolar/subnanomolar inhibitors of the tumor-associated isoforms IX and XII. Alafeefy AM, Isik S, Abdel-Aziz HA, Ashour AE, Vullo D, Al-Jaber NA, Supuran CT. Bioorg. Med. Chem. 21 1396-1403 (2013)
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  12. Synthesis and carbonic anhydrase inhibitory properties of novel 1,4-dihydropyrimidinone substituted diarylureas. Celik F, Arslan M, Yavuz E, Demir D, Gençer N. J Enzyme Inhib Med Chem 29 18-22 (2014)
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  14. Inhibition pattern of sulfamide-related compounds in binding to carbonic anhydrase isoforms I, II, VII, XII and XIV. Gavernet L, Gonzalez Funes JL, Palestro PH, Bruno Blanch LE, Estiu GL, Maresca A, Barrios I, Supuran CT. Bioorg. Med. Chem. 21 1410-1418 (2013)
  15. Carbonic anhydrase inhibitors: design, synthesis, and biological evaluation of novel sulfonyl semicarbazide derivatives. Pichake J, Kharkar PS, Ceruso M, Supuran CT, Toraskar MP. ACS Med Chem Lett 5 793-796 (2014)
  16. Effect of incorporating a thiophene tail in the scaffold of acetazolamide on the inhibition of human carbonic anhydrase isoforms I, II, IX and XII. Biswas S, McKenna R, Supuran CT. Bioorg. Med. Chem. Lett. 23 5646-5649 (2013)
  17. The structural comparison between membrane-associated human carbonic anhydrases provides insights into drug design of selective inhibitors. Alterio V, Pan P, Parkkila S, Buonanno M, Supuran CT, Monti SM, De Simone G. Biopolymers 101 769-778 (2014)
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  19. Synthesis and biological profile of new 1,2,3,4-tetrahydroisoquinolines as selective carbonic anhydrase inhibitors. Gitto R, Damiano FM, De Luca L, Ferro S, Vullo D, Supuran CT, Chimirri A. Bioorg. Med. Chem. 19 7003-7007 (2011)
  20. Synthesis and carbonic anhydrase inhibitory properties of 1,3-dicarbonyl derivatives of methylaminobenzene-sulfonamide. Demirci T, Arslan M, Bilen Ç, Demir D, Gençer N, Arslan O. J Enzyme Inhib Med Chem 29 132-136 (2014)
  21. Synthesis and carbonic anhydrase inhibitory properties of tetrazole- and oxadiazole substituted 1,4-dihydropyrimidinone compounds. Celik F, Arslan M, Kaya MO, Yavuz E, Gencer N, Arslan O. Artif Cells Nanomed Biotechnol 42 58-62 (2014)
  22. Synthesis and evaluation of N-heteroarylsubstituted triazolosulfonamides as carbonic anhydrase inhibitors. Balci A, Arslan M, Nixha AR, Bilen C, Ergun A, Gençer N. J Enzyme Inhib Med Chem 30 377-382 (2015)
  23. Lucky Switcheroo: Dramatic Potency and Selectivity Improvement of Imidazoline Inhibitors of Human Carbonic Anhydrase VII. Kalinin S, Kopylov S, Tuccinardi T, Sapegin A, Dar'in D, Angeli A, Supuran CT, Krasavin M. ACS Med Chem Lett 8 1105-1109 (2017)
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  25. Discovery of New 1,1'-Biphenyl-4-sulfonamides as Selective Subnanomolar Human Carbonic Anhydrase II Inhibitors. La Regina G, Puxeddu M, Nalli M, Vullo D, Gratteri P, Supuran CT, Nocentini A, Silvestri R. ACS Med Chem Lett 11 633-637 (2020)
  26. Synthesis and Biological Evaluation of 4-Sulfamoylphenyl/Sulfocoumarin Carboxamides as Selective Inhibitors of Carbonic Anhydrase Isoforms hCA II, IX, and XII. Angapelly S, Angeli A, Khan AJ, Sri Ramya PV, Supuran CT, Arifuddin M. ChemMedChem 13 1165-1171 (2018)


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