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Research Article

Quantitative structure–activity relationship (QSAR) studies on a series of 1,3,4-thiadiazole-2-thione derivatives as tumor-associated carbonic anhydrase IX inhibitors

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Pages 722-729 | Received 08 Apr 2008, Accepted 11 Jul 2008, Published online: 20 Oct 2008

References

  • C Hansch, T Fujita. A method for the correlation of biological activity and chemical structure. J Am Chem Soc 1964;86:1616–1626.
  • B Prosenjit, R Kounal. QSAR of adenosine A3 receptor antagonist 1,2,4-triazolo[4,3-a]quinoxalin-1-one derivatives using chemometric tools. Bioorg Med Chem Lett 2005;15:3737–3743.
  • MV Diudea. QSAR/QSPR studies by molecular descriptors. Hungtington: Nova Science Publishers; 2000.
  • H Kubinyi, G Folkers, VC Martin. 3D QSAR in drug design ligand–protein interaction and molecularity. Amsterdam, The Netherlands: Klawer/ESCOM; 1998.
  • H Kubinyi, G Folkers, YC Martin. 3D QSAR in drug design: Recent advances. Amsterdam, The Netherlands: Klawer/ESCOM; 1998 .
  • J Devilliers. Comparative QSAR. Washington, DC: Taylor & Francis; 1998.
  • J Devillers, AT Balaban. Topological indices and related descriptors in QSAR and QSPR. Amsterdam, The Netherlands: Gordon and Breach Science Publication; 1999.
  • M Karelson. Molecular descriptors in QSAR/QSPR. New York: John Wiley & Sons; 2000.
  • CT Supuran. Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–181.
  • A Scozzafava, A Mastrolorenzo, CT Supuran. Modulation of carbonic anhydrase activity and its applications in therapy. Expert Opin Ther Patents 2004;14:667–702.
  • CT Supuran. Carbonic anhydrases: Catalytic and inhibition mechanisms, distribution and physiological roles. In: CT Supuran, A Scozzafava, J Conway, editors. Carbonic anhydrase—its inhibitors and activators. Boca Raton: CRC; 2004. p 1–23.
  • CT Supuran, D Vullo, G Manole, A Casini, A Scozzafava. Designing of novel carbonic anhydrase inhibitors and activators. Curr Med Chem Cardiovasc Hematol Agents 2004;2:49–68.
  • S Pastorekova, S Parkkila, J Pastorek, CT Supuran. Proceedings of the 6th International Conference on Carbonic Anhydrases. June, 2003. Bratislava, Slovak Republic. J Enz Inhib Med Chem 2004;19:199–291.
  • CT Supuran. Carbonic anhydrase inhibitors in the treatment and prophylaxis of obesity. Expert Opin Ther Patents 2003;13:1545–1550.
  • E Svastova, A Hulikova, M Rafajova, M Zat'ovicova, A Gibadulinova, A Casini, A Cecchi, A Scozzafava, CT Supuran, J Pastorek, S Pastorekova. Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH. FEBS Lett 2004;577:439–445.
  • CT Supuran. Indisulam: An anticancer sulfonamide in clinical development. Expert Opin Invest Drugs 2003;12:283–287.
  • CT Supuran, A Scozzafava, A Casini. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146–189.
  • A Scozzafava, T Owa, A Mastrolorenzo, CT Supuran. Anticancer and antiviral sulfonamides. Curr Med Chem 2003;10:925–953.
  • D Vullo, M Franchi, E Gallori, J Pastorek, A Scozzafava, S Pastorekova, CT Supuran. Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, cancer-associated isozyme IX with anions. J Enz Inhib Med Chem 2003;18:403–406.
  • D Vullo, M Franchi, E Gallori, J Pastorek, A Scozzafava, S Pastorekova, CT Supuran. Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett 2003;13:1005–1009.
  • JY Winum, D Vullo, A Casini, JL Montero, A Scozzafava, CT Supuran. Carbonic anhydrase inhibitors: Inhibition of transmembrane, tumor-associated isozyme IX, and cytosolic isozymes I and II with aliphatic sulfamates. J Med Chem 2003;46:5471–5477.
  • JY Winum, D Vullo, A Casini, JL Montero, A Scozzafava, CT Supuran. Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors. J Med Chem 2003;46:2197–2204.
  • C Potter, AL Harris. Hypoxia inducible carbonic anhydrase IX, marker of tumour hypoxia, survival pathway and therapy target. Cell Cycle 2004;3:164–167.
  • S Pastorekova, A Casini, A Scozzafava, D Vullo, J Pastorek, CT Supuran. Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX. Bioorg Med Chem Lett 2004;14:869–873.
  • M Rafajova, M Zatovicova, R Kettmann, J Pastorek, S Pastorekova. Induction by hypoxia combined with low glucose or low bicarbonate and high posttranslational stability upon reoxygenation contribute to carbonic anhydrase IX expression in cancer cells. Int J Oncol 2004;24:995–1004.
  • N Robertson, C Potter, AL Harris. Role of carbonic anhydrase IX in human tumor cell growth, survival, and invasion. Cancer Res 2004;64:6160–6165.
  • CT Supuran, A Scozzafava, A Casini. Development of sulfonamide carbonic anhydrase inhibitors. In: CT Supuran, A Scozzafava, J Conway, editors. Carbonic anhydrase—its inhibitors and activators. Boca Raton: CRC; 2004. p 67–147.
  • A Casini, J Antel, F Abbate, A Scozzafava, S David, H Waldeck, S Schafer, CT Supuran. Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV. Bioorg Med Chem Lett 2003;13:841–845.
  • L Bonnac, A Innocenti, JY Winum, A Casini, JL Montero, A Scozzafava, V Barragan, CT Supuran. Carbonic anhydrase inhibitors: Aliphatic N-phosphorylated sulfamates—a novel zinc-anchoring group leading to nanomolar inhibitors. J Enz Inhib Med Chem 2004;19:275–278.
  • A Scozzafava, CT Supuran. Hydroxyurea is a carbonic anhydrase inhibitor. Bioorg Med Chem 2003;11:2241–2246.
  • M Abdel-Hamid, A Abdel-Hafez, N El-Koussi, N Mahfouz, A Innocenti, CT Supuran. Design, synthesis, and docking studies of new 1,3,4-thiadiazole-2-thione derivatives with carbonic anhydrase inhibitory activity. Bioorg Med Chem 2007;15:6975–6984.
  • Molecular Operating Environment (MOE 2005.06) version 2006.02, Chemical Computing Group Inc., 1010 Sherbrooke Street West, Suite 910, Montreal, H3A 2R7, Canada.
  • Chem. 3D Ultra version 8.0, Cambridge Software Corporation, USA.
  • LB Kier, LH Hall. Molecular connectivity in structure activity analysis. USA: John Wiley & Sons Inc.; 1984.
  • Molecular Orbital Package (MOPAC) module (CS MOPAC 2000) of Chem. 3D Ultra version 8.0, Cambridge Software Corporation, USA.
  • M Jaiswal, V Khadikar, A Scozzafava, CT Supuran. Carbonic anhydrase inhibitors: The first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett 2004;14:3283–3290. and references therein
  • E Manivannan, S Prasanna. First QSAR report on FSH receptor antagonistic activity: Quantitative investigations on physico-chemical and structural features among 6-amino-4-phenyltetrahydroquinoline derivatives. Bioorg Med Chem Lett 2005;15:4496–4501.
  • B Narasimhan, M Kumari, N Jain, A Dhake, C Sundaravelan. Correlation of antibacterial activity of some N-[5-(2-furanyl)-2-methyl-4-oxo-4H-thieno[2,3-d]pyrimidin-3-yl]-carboxamide and 3-substituted-5-(2-furanyl)-2-methyl-3H-thieno[2,3-d]pyrimidin-4-ones with topological indices using Hansch analysis. Bioorg Med Chem Lett 2006;16:4951–4958. and references therein
  • G Melagraki, A Afantitis, H Sarimveis, O Igglessi-Markopoulou, CT Supuran. QSAR study on para-substituted aromatic sulfonamides as carbonic anhydrase II inhibitors using topological information indices. Bioorg Med Chem 2006;14:1108–1114.

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