Abstract
2-amino-4-(4-chloro phenyl)-1,3-thiazole (1) was synthesized by refluxing thiourea with para-chloro phenacyl bromide in absolute methanol. The condensation of amine compound (1) with phenylisothiocyanate in the presence of pyridine will produce 1-(4-(4-chlorophenyl)thiazol-2-yl)-3-phenylthiourea(2), which is upon treatment with 2,4 dinitrophenyl hydrazine by conventional method, afforded 1- ( 4 - ( 4 – chlorophenyl ) thiazol – 2 – yl ) – 3 - phenylhydrazonamide,N' - ( 2 , 4 -dinitrophenyl) ,(3).The characterization of the titled compounds were performed utilizing FTIR spectroscopy, 1HNMR and CHNS elemental analysis, and by measurements of their physical properties. The synthesized compounds had been screened for their, in vitro preliminary antimicrobial activity against three Gram-positive bacteria: (Staph. aureus, Micrococcus luteus and Bacillus subtilis) and three Gram-negative bacteria : (Pseud.aeruginosa, E.coli and Proteus mirabilis) ,and two fungal strains(Candida albicans and Candida glabrata ), using a minimum inhibitory concentration (MIC) of 100 µg\ml of test compound, by well diffusion method.
 The derivatives showed moderate antibacterial activity against Gram-positive Staphylococcus aureus and Bacillus subtilis & high antifungal activity against Candida glabrata and Candida albicans. Computational study was performed to calculate some of thermodynamic parameters by using density functional theory (DFT)
Highlights
Thiazoles are significantly important heterocyclic that represent interesting properties depending on the linked groups to the thiazole[1]. 2-aminothiazoles are a subclass of thiazole family that are of high interest due to their broad biological activity., fungicidal[2], antioxidative [3], analgesic [4], bactericidal [5] and anti-inflammatory
Chemicals used during the synthesis, supplied by hyper- chem/china
Completion of reactions and the purity of compounds were ascertained by thin-layer chromatography (TLC), using Silica gel GF254 precoated Aluminium sheets, Merck (Germany) exposed to UV-254nm light and the eluent used is n-hexane: ethyl acetate (6.0:4.0) for compound [1], n-hexane: ethyl acetate (8.0:2.0)
Summary
Thiazoles are significantly important heterocyclic that represent interesting properties depending on the linked groups to the thiazole[1]. 2-aminothiazoles are a subclass of thiazole family that are of high interest due to their broad biological activity., fungicidal[2], antioxidative [3], analgesic [4], bactericidal [5] and anti-inflammatory [5],anti-HIV [6], antitubercular [7], Thiazole containing N=C=S moiety have been used as antiphychotics [8]and antimalarial [9], and as herbicidal [10] .Thiazoles have broadly been engaged as effective γsecretase inhibitors to hinder Alzheimer’s disease [11] and have a lot of derivations and because of its derivations type have a lot of application in various industries, medical science, and pharmacy.In 1887, Hantzsch et al identified and established molecular structure of thiazoles. In 1889, the first derivation of thiazoles identified by Prop et al and was named 2-amino thiazole [12]. Thiazole and related compounds are called 1 , 3 - azoles ( nitrogen and one other heteroatom in a five – membered ring ). They are isomeric with the 1 , 2 – bazoles , the nitrogen , and sulfur compound being called isothiazole [15]. Iraqi Journal of Pharmaceutical Sciences compounds from readily available reagents is one of the major challenges in organic chemistry. Among the wide variety of heterocycles that have been explored for developing pharmaceutically molecules [16].Our study focuses on derivatization of new molecules starting from the parent nucleus 2-
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