Abstract
In general, benzothiazole derivatives have attracted great interest due to their pharmaceutical and biological importance. New 2-amino-6-arylbenzothiazoles were synthesized in moderate to excellent yields via Suzuki cross coupling reactions using various aryl boronic acids and aryl boronic acid pinacol esters and the antiurease and nitric oxide (NO) scavenging activity of the products were also examined. The most active compound concerning urease enzyme inhibition was 6-phenylbenzo[d]thiazole-2-amine 3e, with an IC50 value of 26.35 µg/mL. Compound 3c, 6-(4-methoxyphenyl) benzo[d]thiazole-2-amine, exhibited the highest nitric oxide percentage scavenging at 100 µg/mL.
Highlights
IntroductionNowadays the benzothiazole moiety has great scientific importance as it is a weak base heterocyclic compound having numerous biological activities such as anti-inflammatory [1], analgesics [2], antitumor [3], antibacterial [4], antihistamines [5], suchistosomicidal [6] and antivirus properties [7]
We have investigated the Suzuki cross coupling reactions of 2-amino-6-bromobenzothiazole (2) with various aryl boronic acids and esters under optimized heating conditions
There is a very little work on the synthesis of 2-amino-6-aryl benzothiazoles 3a–e so far and limited information has been published on the urease enzyme inhibition and nitric oxide (NO) scavenging activities of 2-amino-6-arylbenzothiazole derivatives. 2-Amino-6-bromobenzothiazole (2) was prepared stirring by 4-bromoaniline with acetic acid (0.011 mol) and potassium thiocynate (0.044 mol) in solution of bromine (0.011 mol) in AcOH
Summary
Nowadays the benzothiazole moiety has great scientific importance as it is a weak base heterocyclic compound having numerous biological activities such as anti-inflammatory [1], analgesics [2], antitumor [3], antibacterial [4], antihistamines [5], suchistosomicidal [6] and antivirus properties [7]. Vicendo and coworkers have synthesized new class of thiol and aminothiol compounds derived from benzothiazole and thiadiazole and checked their ability to scavenge free radical (ABTS.+, .OH, DPPH.). On the basis of QSAR and DFT studies of thiazole and benzothiazole molecules, it has been observed that these compounds are potential antioxidant agents and free radical scavengers [13]. The Suzuki cross coupling reaction has developed as a powerful method in organic synthesis [16]. Piscitelli and coworker reported the treatment of 4-substituated anilines with potassium thiocyanate in the presence of bromine in acetic acid for the synthesis of 6-substituted 2-aminobenzothiazoles and further their Suzuki cross coupling reactions in the presence of Pd(PPh3) under. Suzuki cross coupling chemistry and to investigate the antiurease, NO activity of the products on the basis of previously studied hetroaryl molecules as strong urease inhibitors and NO scavengers
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