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Synthesis and Biological Evaluation of Sugar Induced Thiazole Derivatives

Md. Mosharef Hossain Bhuiyan
Department of Chemistry, University of Chittagong, Chittagong-4331, Bangladesh

Mohammed M. Matin
Department of Chemistry, University of Chittagong, Chittagong-4331, Bangladesh

A. F. M. Hafizur Rahman
Department of Analytical Chemistry & Environmental Science, Training Institute for Chemical Industries (TICI), Polash, Norsingdi-1611, Bangladesh

Md. Rabiul Alam
Department of Chemistry, Comilla University, Kotbari, Cumilla

Abstract/ Executive Summary:

The starting materials, 2-amino-4-phenylthiazole and 2-amino-4,5,6,7- tetrahydrobenzo[d]thiazole, were prepared by reacting thiourea with acetophenone and cyclohexanone in the presence of iodine under heating on a water bath with occasional stirring, respectively. Reaction of 2-amino-4-phenylthiazole and 2- amino-4,5,6,7-tetrahydrobenzo[d]thiazole with various sugars afforded corresponding N-glycoside derivatives in good yields. The structures of the synthesized N-glycosides derivatives have been established on the basis of their IR and NMR spectral data. The obtained compounds were screened for their antimicrobial activity. Some of them were found to possess significant activities when compared to standard drugs.

Keywords: Aminothiazole, Sugar, N-Glycoside, Antimicrobial activity

Location: In Bangladesh

Start Date:

End Date:

Program Area: Conservation and Biodiversity

Commodity: Sugarcane

Objectives:

To describes the synthesis, characterization and antimicrobial evaluation of some new N-glycosides having substituted thiazole moiety.

Methodology:

Melting points were recorded with Electrothermal melting point apparatus and are uncorrected. Evaporation of solvents was performed under reduced pressure on a Buchi rotary evaporator. Thin-layer chromatography was performed on Kieselgel GF254 and visualization was accomplished by Iodine Flask or UV Lamp. Column chromatography was carried out with silica gel G60 (100-200 mesh). ¹H-NMR (400 MHz) and ¹³C-NMR (100 MHz) spectra were recorded for solutions in deuterioted chloroform CDCl₃ as solvent. Chemical shifts were reported in δ unit (ppm) with reference to TMS as an internal standard. The antibacterial activities of thiazolo sugar derivatives were studied against six bacteria and antifungal activities of the same compounds were also studied against five fungi. For the detection of antibacterial activity, the disc diffusion method was followed. The antifungal activity was assessed by the poisoned food technique. Paper disc of 4 mm in diameter and Petri plate of 100 mm in diameter were used throughout the experiment culture plated were made with sterilized methods NA (45 ºC) and after solidification of agar medium, the test organizations (suspensions) were pressed uniformly over the plate with sterilized glass rod separately. The paper discs after soaking with test chemicals at the rate 10 mg/disc (100 mg/disc) were placed at the center on the inoculated pour plate. A control plate was also maintained in each case with DMF. These were kept for 4 hours at low temperature (4 ºC) and test chemicals diffused from disc to the surrounding medium by this time. The plates were than incubated at (35+2) ºC for the growth of test organisms and were observed at 24 hours intervals for two days. The activity is expressed in terms of diameters of 24 hours intervals for two days. The activity is expressed in terms of diameters of zone of inhibition in mm. Each experiment was reported thrice. The test chemicals (1%) were mixed with sterilized potato dextrose agar (PDA) medium (42 ⁰C) of the rate 100 mg/ml PDA. The medium was poured in a sterilized Petri plate and after solidification, the equal diameter of fungal inoculums block (10 mm mycelial block) was pleased on the center of the Petri plates. Radial growth of fungal colony was measured in mm after 3-5 of incubation at (25+2) ⁰C a control set was maintained in each experimental using only PDA with DMF of 1% as growth medium. Each experiment repeated thrice. The percentage inhibition of mycelial growth of the test fungi was calculated as follows: I = {(C-T)/T} x 100. Where, I = Percentage of inhibition, C = Diameter of the fungal colony in control (DMF), T = Diameter of the fungal colony in treatment.

Source of Information: The Chittagong Univ. J. Sci. 41(1) : 68-84, 2019

Article Link (Online Journal): DOI: https://doi.org/10.3329/cujs.v41i1.51915

Funding Source:

Budget:

Total Budget (Tk.) :

Achievement/Findings:

In this work, we have demonstrated the syntheses of sugar induced N-glycosides with promising antibacterial and antifungal activity. The activity data obtained during the study will be certainly useful to go for further research for drug designing and synthesizing new thiazole derivatives.

Knowledge Management: Journal