Abstract
To combat the antimicrobial and anticancer drug resistance by pathogens and cancerous cells, efforts has been made to study the pharmacological activities of newly synthesized N-(4-(4-bromophenyl)thiazol-2-yl)-2-chloroacetamide derivatives. The molecular structures of the synthesized derivatives were confirmed by their physicochemical properties and spectroanalytical data (NMR, IR and elemental). The synthesized compounds were evaluated for their in vitro antimicrobial activity against bacterial (Gram positive and Gram negative) and fungal species using turbidimetric method and anticancer activity against oestrogen receptor positive human breast adenocarcinoma cancer cell line (MCF7) by Sulforhodamine B (SRB) assay. Molecular docking studies were carried out to study the binding mode of active compounds with receptor using Schrodinger v11.5. The antimicrobial activity results revealed that compounds d1, d2 and d3 have promising antimicrobial activity. Anticancer screening results indicated that compounds d6 and d7 were found to be the most active ones against breast cancer cell line. Furthermore, the molecular docking study demonstrated that compounds d1, d2, d3, d6 and d7 displayed good docking score within binding pocket of the selected PDB ID (1JIJ, 4WMZ and 3ERT) and has the potential to be used as lead compounds for rational drug designing.
Highlights
The indiscriminate use of antimicrobial agents has resulted in microbial resistance which has reached on alarming level [1]
P-bromoacetophenone and thiourea were reacted in the presence of catalyst iodine to afford the intermediate 4-(4-bromophenyl) thiazol-2-amine (Step a, Int-I)
The presence of singlet at 7.4–7.902 δ ppm indicated the CONH connectivity, Scheme 1 For the synthesis of N-(4-(4-bromophenyl)thiazol-2-yl)-2-chloroacetamide derivatives confirming of the presence of amide linkage within the synthesized derivatives
Summary
The indiscriminate use of antimicrobial agents has resulted in microbial resistance which has reached on alarming level [1]. This necessitates the need for discovery and development of new molecules from the natural or synthetic sources with novel mode of action to Sharma et al BMC Chemistry (2019) 13:46. It was found that thiazole ring is essential for the antimicrobial [1] and anticancer [15, 16] activities. The presence of electron withdrawing group as para-aromatic substituent on 1,3-thiazole nucleus and amide linkage within the molecule can be considered as a useful template for antitumor activity [14, 17]. Prajapti et al and Singh et al reported that amino thiazole derivatives with amide linkage exhibit good antibacterial and antifungal activity [12, 18].
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