Synthesis and bioactivity of several new hetaryl sulfonamides

Parham Taslimi,Afsun Sujayev,Sevgi Mamedova,Pınar Kalın,İlhami Gulçin,Nastaran Sadeghian,Sukru Beydemir,O Irfan Kufrevioglu,Saleh H Alwasel,Vagif Farzaliyev,Sabir Mamedov

doi:10.1080/14756366.2016.1238367

Abstract

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.

Highlights

Pyridine thione compounds are the building blocks of drugs that improve cerebral blood flow
It was observed that the reaction of acetamide benzenesulfonyl chloride in the presence of DMSO is connected with chitosan derivatives[7]
The synthesis of 1-(4-methylsulfonyl)-2-thione-4-aryl-5-Z-6-methyl and oxyalkyl-imidazoles is reported in Scheme 1

Summary

Introduction

Pyridine thione compounds are the building blocks of drugs that improve cerebral blood flow (nimodipinum, nifedipinum (calcium channel blockers). The synthesis of new sulfonamides containing bicyclic compounds is relevant, the reaction of aryl sulfonyl chlorides with heterocyclic amines. Studies of aryl sulfonyl chloride reactions with heterocyclic and bicyclic amines are important for both obtaining new sulfonamide compounds and investigating their germicidal and other properties[8].

Results

Conclusion