Synthesis and bioactivity of several new hetaryl sulfonamides

• Published in: Journal of enzyme inhibition and medicinal chemistry Vol. 32; no. 1; pp. 137 - 145
• Main Authors: Taslimi, Parham, Sujayev, Afsun, Mamedova, Sevgi, Kalın, Pınar, Gulçin, İlhami, Sadeghian, Nastaran, Beydemir, Sukru, Kufrevioglu, O. Irfan, Alwasel, Saleh H., Farzaliyev, Vagif, Mamedov, Sabir
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis 01.01.2017; Taylor & Francis Ltd; Taylor & Francis Group
• Subjects: Acetazolamide; Acetylcholinesterase; Acetylcholinesterase - metabolism; Antibiotics; Antioxidants; aryl sulfonyl chlorides; Biochemistry & Molecular Biology; Biological activity; butyrylcholinesterase; Butyrylcholinesterase - metabolism; carbonic anhydrase; Carbonic Anhydrase Inhibitors - chemical synthesis; Carbonic Anhydrase Inhibitors - pharmacology; Carbonic anhydrases; Carbonic Anhydrases - metabolism; Chemistry, Medicinal; Chloride; Enzymes; Erythrocytes; Food; heterocyclic amines; Humans; Hydrochloric acid; Isoenzymes; Life Sciences & Biomedicine; Original; Pharmaceutical sciences; Pharmacology & Pharmacy; Phenols; Science & Technology; Sulfonamides; Sulfonamides - chemical synthesis; Sulfonamides - pharmacology; Sulfur; Tacrine; butyrylcholinesterase; heterocyclic amines; PHENOLIC-COMPOUNDS; INHIBITORY PROPERTIES; Acetylcholinesterase; CARBONIC-ANHYDRASE ENZYME; ACETYLCHOLINESTERASE INHIBITION; IN-VITRO ANTIOXIDANT; ISOENZYMES HCA I; POLYPHENOL CONTENT; PURIFICATION; carbonic anhydrase; TROUT ONCORHYNCHUS-MYKISS; DERIVATIVES; aryl sulfonyl chlorides
• ISSN: 1475-6366; 1475-6374
• DOI: 10.1080/14756366.2016.1238367

1-(4-Methylsulfonyl)-2-thione-4-aryl-5-Z-6-methyl and oxyalkyl-imidazoles were synthesized from different tetrahydropyrimidinethiones and aryl sulfonyl chloride. These compunds were tested for metal chelating effects and to determine the phrase in which inhibition occured between two physiologically pertinent compunds and carbonic anhydrase (CA) isozymes I and II (hCA I and II), butyrylcholinesterase (BChE) and acetylcholinesterase (AChE). AChE was detected in high concentrations in the brain and red blood cells. BChE is another enzymes that is abundant available in the liver and released into the blood in a soluble form. Newly synthesized hetaryl sulfonamides exhibited impressive inhibition profiles with Ki values in the range of 1.42-6.58 nM against hCA I, 1.72-7.41 nM against hCA II, 0.20-1.14 nM against AChE and 1.55-5.92 nM against BChE. Moreover, acetazolamide showed Ki values of 43.69 ± 6.44 nM against hCA I and 31.67 ± 8.39 nM against hCA II. Additionally, tacrine showed Ki values of 25.75 ± 3.39 nM and 37.82 ± 2.08 against AChE and BChE, respectively.