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Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors.
Bioorg Med Chem. 2017 06 15; 25(12):3093-3097.BM

Abstract

A series of sixteen novel aromatic and heterocyclic bis-sulfonamide Schiff bases were prepared by conjugation of well known aromatic and heterocyclic aminosulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitor pharmacophores with aromatic and heterocyclic bis-aldehydes. The obtained bis-sulfonamide Schiff bases were investigated as inhibitors of four selected human (h) CA isoforms, hCA I, hCA II, hCA VII and hCA IX. Most of the newly synthesized compounds showed a good inhibitory profile against isoforms hCA II and hCA IX, also showing moderate selectivity against hCA I and VII. Several efficient lead compounds were identified among this bis-sulfonamide Schiff bases with low nanomolar to sub-nanomolar activity against hCA II (Kis ranging between 0.4 and 861.1nM) and IX (Kis between 0.5 and 933.6nM). Since hCA II and hCA IX are important drug targets (antiglaucoma and anti-tumor agents), these isoform-selective inhibitors may be considered of interest for various biomedical applications.

Authors+Show Affiliations

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Adiyaman University, 02040 Adiyaman, Turkey. Electronic address: akocaksuleyman@gmail.com.Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Adiyaman University, 02040 Adiyaman, Turkey.Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino (Florence), Italy.Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Adiyaman University, 02040 Adiyaman, Turkey.Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Adiyaman University, 02040 Adiyaman, Turkey.Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino (Florence), Italy. Electronic address: claudiu.supuran@unifi.it.

Pub Type(s)

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

Language

eng

PubMed ID

28400084

Citation

Akocak, Suleyman, et al. "Synthesis and Biological Evaluation of Novel Aromatic and Heterocyclic Bis-sulfonamide Schiff Bases as Carbonic Anhydrase I, II, VII and IX Inhibitors." Bioorganic & Medicinal Chemistry, vol. 25, no. 12, 2017, pp. 3093-3097.
Akocak S, Lolak N, Nocentini A, et al. Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors. Bioorg Med Chem. 2017;25(12):3093-3097.
Akocak, S., Lolak, N., Nocentini, A., Karakoc, G., Tufan, A., & Supuran, C. T. (2017). Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors. Bioorganic & Medicinal Chemistry, 25(12), 3093-3097. https://doi.org/10.1016/j.bmc.2017.03.063
Akocak S, et al. Synthesis and Biological Evaluation of Novel Aromatic and Heterocyclic Bis-sulfonamide Schiff Bases as Carbonic Anhydrase I, II, VII and IX Inhibitors. Bioorg Med Chem. 2017 06 15;25(12):3093-3097. PubMed PMID: 28400084.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors. AU - Akocak,Suleyman, AU - Lolak,Nabih, AU - Nocentini,Alessio, AU - Karakoc,Gulcin, AU - Tufan,Anzel, AU - Supuran,Claudiu T, Y1 - 2017/03/31/ PY - 2017/03/08/received PY - 2017/03/27/revised PY - 2017/03/29/accepted PY - 2017/4/13/pubmed PY - 2017/8/2/medline PY - 2017/4/13/entrez KW - Bis-sulfonamide KW - Carbonic anhydrase KW - Isoform-selective inhibitor KW - Schiff base SP - 3093 EP - 3097 JF - Bioorganic & medicinal chemistry JO - Bioorg. Med. Chem. VL - 25 IS - 12 N2 - A series of sixteen novel aromatic and heterocyclic bis-sulfonamide Schiff bases were prepared by conjugation of well known aromatic and heterocyclic aminosulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitor pharmacophores with aromatic and heterocyclic bis-aldehydes. The obtained bis-sulfonamide Schiff bases were investigated as inhibitors of four selected human (h) CA isoforms, hCA I, hCA II, hCA VII and hCA IX. Most of the newly synthesized compounds showed a good inhibitory profile against isoforms hCA II and hCA IX, also showing moderate selectivity against hCA I and VII. Several efficient lead compounds were identified among this bis-sulfonamide Schiff bases with low nanomolar to sub-nanomolar activity against hCA II (Kis ranging between 0.4 and 861.1nM) and IX (Kis between 0.5 and 933.6nM). Since hCA II and hCA IX are important drug targets (antiglaucoma and anti-tumor agents), these isoform-selective inhibitors may be considered of interest for various biomedical applications. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/28400084/Synthesis_and_biological_evaluation_of_novel_aromatic_and_heterocyclic_bis_sulfonamide_Schiff_bases_as_carbonic_anhydrase_I_II_VII_and_IX_inhibitors_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(17)30467-4 DB - PRIME DP - Unbound Medicine ER -