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New aminobenzenesulfonamide-thiourea conjugates: synthesis and carbonic anhydrase inhibition and docking studies.
Eur J Med Chem. 2014 May 06; 78:140-50.EJ

Abstract

A variety of 1-substituted-3-(3-aminosulfonylphenyl)thioureas (3a-k) and two new 1-aroyl-3-(4-aminosulfonylphenyl)thiourea derivatives (5a and 5b) were synthesized by reaction of 3-aminobenzenesulfonamide and 4-aminobenzenesulfonamide respectively with freshly prepared aroyl/heteroaryl isothiocyanates in dry acetonitrile. FTIR, (1)H NMR, (13)C NMR, GC-MS and elemental analyses data confirmed the assigned structures to the synthesized compounds. Further structure of compound (3g) was also confirmed by single crystal XRD analysis. The compounds were investigated as inhibitors of the bovine erythrocyte carbonic anhydrase isoform II (bCA II). The inhibition constants of these compounds against bCA II were in the range 0.011-17.1 μM. Among the evaluated compounds, 1-substituted -3-(3-aminosulfonylphenyl)thiourea derivatives 3h and 5a were the most potent inhibitors with IC50 of 0.052 and 0.011 μM, respectively. In silico docking and molecular dynamics simulation studies were performed against bCA II and human CA II enzymes to rationalize the inhibitory properties of these compounds.

Authors+Show Affiliations

Centre for Advanced Drug Research, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan. Electronic address: aamersaeed@yahoo.com.Department Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany.Department Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany.Department of Bioinformatics, Fraunhofer Institute SCAI, Sankt Augustin, Germany.Centre for Advanced Drug Research, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan; Department of Pharmaceutical Sciences, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan. Electronic address: drjamshed@ciit.net.pk.

Pub Type(s)

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

Language

eng

PubMed ID

24681391

Citation

Zaib, Sumera, et al. "New Aminobenzenesulfonamide-thiourea Conjugates: Synthesis and Carbonic Anhydrase Inhibition and Docking Studies." European Journal of Medicinal Chemistry, vol. 78, 2014, pp. 140-50.
Zaib S, Saeed A, Stolte K, et al. New aminobenzenesulfonamide-thiourea conjugates: synthesis and carbonic anhydrase inhibition and docking studies. Eur J Med Chem. 2014;78:140-50.
Zaib, S., Saeed, A., Stolte, K., Flörke, U., Shahid, M., & Iqbal, J. (2014). New aminobenzenesulfonamide-thiourea conjugates: synthesis and carbonic anhydrase inhibition and docking studies. European Journal of Medicinal Chemistry, 78, 140-50. https://doi.org/10.1016/j.ejmech.2014.03.023
Zaib S, et al. New Aminobenzenesulfonamide-thiourea Conjugates: Synthesis and Carbonic Anhydrase Inhibition and Docking Studies. Eur J Med Chem. 2014 May 6;78:140-50. PubMed PMID: 24681391.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - New aminobenzenesulfonamide-thiourea conjugates: synthesis and carbonic anhydrase inhibition and docking studies. AU - Zaib,Sumera, AU - Saeed,Aamer, AU - Stolte,Karin, AU - Flörke,Ulrich, AU - Shahid,Mohammad, AU - Iqbal,Jamshed, Y1 - 2014/03/12/ PY - 2013/12/25/received PY - 2014/02/16/revised PY - 2014/03/08/accepted PY - 2014/4/1/entrez PY - 2014/4/1/pubmed PY - 2014/12/30/medline KW - 1-Aroyl/heteroaryl-3-(3-aminosulfonylphenyl)thioureas KW - 3-Aminobenzenesulfonamide KW - Carbonic anhydrase KW - Molecular dynamics simulation SP - 140 EP - 50 JF - European journal of medicinal chemistry JO - Eur J Med Chem VL - 78 N2 - A variety of 1-substituted-3-(3-aminosulfonylphenyl)thioureas (3a-k) and two new 1-aroyl-3-(4-aminosulfonylphenyl)thiourea derivatives (5a and 5b) were synthesized by reaction of 3-aminobenzenesulfonamide and 4-aminobenzenesulfonamide respectively with freshly prepared aroyl/heteroaryl isothiocyanates in dry acetonitrile. FTIR, (1)H NMR, (13)C NMR, GC-MS and elemental analyses data confirmed the assigned structures to the synthesized compounds. Further structure of compound (3g) was also confirmed by single crystal XRD analysis. The compounds were investigated as inhibitors of the bovine erythrocyte carbonic anhydrase isoform II (bCA II). The inhibition constants of these compounds against bCA II were in the range 0.011-17.1 μM. Among the evaluated compounds, 1-substituted -3-(3-aminosulfonylphenyl)thiourea derivatives 3h and 5a were the most potent inhibitors with IC50 of 0.052 and 0.011 μM, respectively. In silico docking and molecular dynamics simulation studies were performed against bCA II and human CA II enzymes to rationalize the inhibitory properties of these compounds. SN - 1768-3254 UR - https://www.unboundmedicine.com/medline/citation/24681391/New_aminobenzenesulfonamide_thiourea_conjugates:_synthesis_and_carbonic_anhydrase_inhibition_and_docking_studies_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0223-5234(14)00227-X DB - PRIME DP - Unbound Medicine ER -