Heterocycles Derived from 5‐(2‐Aminothiazol‐4‐yl)‐8‐hydroxyquinoline: Synthesis and Antimicrobial Activity

Abstract

5-(2-Aminothiazol-4-yl)-8-hydroxyquinoline 2 has been synthesized by treating thiourea with 5-chloroacetyl-8-hydroxyquinoline 1. The amine 2 was treated with aromatic aldehydes to furnish schiff bases 6a-c which on treatment with phenyl isothiocyanate gave the corresponding thiazolo-s-triazines 7a-c. Reaction of 2 with phenyl isothiocyanate gave the corresponding aminocarbothiamide derivative 8 which on reaction with malonic acid in acetyl chloride afforded thiobarbituric acid derivative 9. Coupling of 9 with diazonium salt gave the phenyl hydrazono derivative 10. However, reaction of 2 with carbon disulphide and methyl iodide afforded dithiocarbamidate 12 which on treatment with ethylenediamine, o-aminophenol and/or phenylenediamine gave the aminoazolo derivatives 13-15, respectively. Other substituted fused thiazolopyrimidines 16-20 have been also prepared by the reaction of 2 with some selected dicarbonyl reagents. The characterisation of synthesized compounds has been done on the basis of elemental analysis, IR, 1 H-NMR and mass spectral data. All the newly synthesized compounds have been screened for their antimicrobial activities.

Synthesis, Biological Properties, and Molecular Docking Study of Novel 1,2,3-Triazole-8-quinolinol Hybrids

“…29 Nonetheless, some reports indicate that the hybridization of 8-quinolinol with other antibacterial pharmacophores has resulted in increased antibacterial efficacy. 30,31 Theoretical computations constitute one of the most oftenused methodologies nowadays. However, theoretical computations have become more feasible and speedier as technology has advanced.…”

HPLC purification technique: synthesis of unsymmetrical thiobarbituric acids

“…TBAs have gained considerable attention and their biological scaffold such as antimicrobial, antitubercular [14, 15], antifungal [16], antitumor [17], antidiabetic and antibacterial activities [18]. TBAs are good building block to be use in varied organic transformations as precursor [19, 20, 21, 22]. Hence, large number of efforts are being made to find out new routes and methodologies for the synthesis of TBAs [23, 24].…”

Benzo[h]thiazolo[2,3-b]quinazolines by an efficient p-toluenesulfonic acid-catalyzed one-pot two-step tandem reaction

“…In recent years, increasing interest has been focused on synthesis of thiazolopyrimidine and thiazoloquinazoline derivatives owing to their significant biological activities that include antimicrobial [1,2], antiviral [3], antioxidant [4], anticancer [5], antiinflammatory [6], antihypertensive [7], antiparkinsonian [8], anti-human immunodeficiency virus (HIV) [9], and antibiofilm [10] properties. They have also been reported as calcium antagonists [11], group 2 metabotropic glutamate receptor antagonists [12], 5-HT2 receptor antagonists [13,14], and inhibitors of enzymes such as xanthine oxidase [15], acetylcholinesterase [16], and CDC25B phosphatise [17].…”