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Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII.
Bioorg Med Chem. 2015 Oct 15; 23(20):6573-80.BM

Abstract

By using a multi component reaction system (MCR), nitro acridine sulfonamides were obtained from cyclic-1,3-diketones, 4-aminobenzene sulfonamide and aromatic aldehydes. Some novel acridine bis-sulfonamides 6a-l were then synthesized by the reaction between sulfonyl chlorides and the novel amino-acridine sulfonamides 5a and 5b, obtained by reduction of nitro-acridine sulfonamide derivatives 4a and 4b. The newly synthesized compounds were investigated as inhibitors of 4 human carbonic anhydrase isoforms (hCA, EC 4.2.1.1). Several of the compounds showed low micromolar inhibition against the medically relevant isoforms hCA I, II, IX, and XII.

Authors+Show Affiliations

Chemistry Department, Faculty of Arts and Science, Dumlupınar University, 43100 Kütahya, Turkey.Chemistry Department, Faculty of Arts and Science, Dumlupınar University, 43100 Kütahya, Turkey.Chemistry Department, Faculty of Arts and Science, Dumlupınar University, 43100 Kütahya, Turkey.Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche e Nutraceutiche, 50019 Sesto Fiorentino (Florence), Italy.Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche e Nutraceutiche, 50019 Sesto Fiorentino (Florence), Italy. Electronic address: claudiu.supuran@unifi.it.Biochemistry Department, Faculty of Arts and Science, Dumlupınar University, 43100 Kütahya, Turkey. Electronic address: muharrem.kaya@dpu.edu.tr.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26422787

Citation

Esirden, İbrahim, et al. "Synthesis of Novel Acridine Bis-sulfonamides With Effective Inhibitory Activity Against the Carbonic Anhydrase Isoforms I, II, IX and XII." Bioorganic & Medicinal Chemistry, vol. 23, no. 20, 2015, pp. 6573-80.
Esirden İ, Ulus R, Aday B, et al. Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII. Bioorg Med Chem. 2015;23(20):6573-80.
Esirden, İ., Ulus, R., Aday, B., Tanç, M., Supuran, C. T., & Kaya, M. (2015). Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII. Bioorganic & Medicinal Chemistry, 23(20), 6573-80. https://doi.org/10.1016/j.bmc.2015.09.022
Esirden İ, et al. Synthesis of Novel Acridine Bis-sulfonamides With Effective Inhibitory Activity Against the Carbonic Anhydrase Isoforms I, II, IX and XII. Bioorg Med Chem. 2015 Oct 15;23(20):6573-80. PubMed PMID: 26422787.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII. AU - Esirden,İbrahim, AU - Ulus,Ramazan, AU - Aday,Burak, AU - Tanç,Muhammet, AU - Supuran,Claudiu T, AU - Kaya,Muharrem, Y1 - 2015/09/15/ PY - 2015/07/20/received PY - 2015/09/10/revised PY - 2015/09/14/accepted PY - 2015/10/1/entrez PY - 2015/10/1/pubmed PY - 2016/4/27/medline KW - Acridine KW - Carbonic anhydrase KW - Enzyme inhibition KW - Isoforms CA I, II, IX and VII KW - Sulfonamide SP - 6573 EP - 80 JF - Bioorganic & medicinal chemistry JO - Bioorg. Med. Chem. VL - 23 IS - 20 N2 - By using a multi component reaction system (MCR), nitro acridine sulfonamides were obtained from cyclic-1,3-diketones, 4-aminobenzene sulfonamide and aromatic aldehydes. Some novel acridine bis-sulfonamides 6a-l were then synthesized by the reaction between sulfonyl chlorides and the novel amino-acridine sulfonamides 5a and 5b, obtained by reduction of nitro-acridine sulfonamide derivatives 4a and 4b. The newly synthesized compounds were investigated as inhibitors of 4 human carbonic anhydrase isoforms (hCA, EC 4.2.1.1). Several of the compounds showed low micromolar inhibition against the medically relevant isoforms hCA I, II, IX, and XII. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/26422787/Synthesis_of_novel_acridine_bis_sulfonamides_with_effective_inhibitory_activity_against_the_carbonic_anhydrase_isoforms_I_II_IX_and_XII_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(15)30047-X DB - PRIME DP - Unbound Medicine ER -