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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.

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Authors+Show Affiliations

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

MeSH

Antigens, NeoplasmCarbonic Anhydrase ICarbonic Anhydrase IICarbonic Anhydrase IXCarbonic Anhydrase InhibitorsCarbonic AnhydrasesDose-Response Relationship, DrugHumansMolecular StructureStructure-Activity Relationship

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 -

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