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. 2019 Apr 23;13(1):60.
doi: 10.1186/s13065-019-0575-x. eCollection 2019 Dec.

4-(4-Bromophenyl)-thiazol-2-amine derivatives: synthesis, biological activity and molecular docking study with ADME profile

Deepika Sharma  1 , Sanjiv Kumar  1 , Balasubramanian Narasimhan  1 , Kalavathy Ramasamy  2   3 , Siong Meng Lim  2   3 , Syed Adnan Ali Shah  2   4 , Vasudevan Mani  5
Affiliations

4-(4-Bromophenyl)-thiazol-2-amine derivatives: synthesis, biological activity and molecular docking study with ADME profile

Deepika Sharma et al. BMC Chem. .

Abstract

In order to overcome the challenges of microbial resistance as well as to improve the effectiveness and selectivity of chemotherapeutic agents against cancer, a novel series of 4-(4-bromophenyl)-thiazol-2-amine derivatives was synthesized and its molecular structures were confirmed by physicochemical and spectral characteristics. The synthesized compounds were further evaluated for their in vitro antimicrobial activity using turbidimetric method and anticancer activity against oestrogen receptor positive human breast adenocarcinoma cancer cell line (MCF7) by Sulforhodamine B (SRB) assay. The antimicrobial activity results revealed that compound p2, p3, p4 and p6 exhibited promising antimicrobial activity that are comparable to standard norfloxacin (antibacterial) and fluconazole (antifungal). Anticancer screening results demonstrated that compound p2 was found to be the most active one against cancer cell line when compared to the rest of the compounds and comparable to the standard drug (5-fluorouracil). The molecular docking study demonstrated that compounds, p2, p3, p4 and p6 displayed good docking score within binding pocket of the selected PDB ID (1JIJ, 4WMZ and 3ERT) and showed promising ADME properties.

Keywords: Anticancer; Antimicrobial; Molecular docking; Synthesis; Thiazole derivatives.

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Conflict of interest statement

The authors declare that they have no competing interests.

Figures

Fig. 1
Fig. 1
Marketed preparation of thiazole nucleus
Fig. 2
Fig. 2
Design of proposed thiazole molecules for antimicrobial and anticancer potential based on literature
Scheme 1
Scheme 1
For the synthesis of 4-(4-bromophenyl)thiazol-2-amine derivatives (p1–p10)
Fig. 3
Fig. 3
Graphical representation of antibacterial activity of synthesized compounds
Fig. 4
Fig. 4
Graphical representation of antifungal activity of synthesized compounds
Fig. 5
Fig. 5
Graphical representation of anticancer activity of synthesized compounds
Fig. 6
Fig. 6
Pictorial presentation (3D) and Ligand interaction diagram (2D) of most active antibacterial compounds (p2, p3 and p4) and standard norfloxacin
Fig. 7
Fig. 7
Pictorial presentation (3D) and ligand interaction diagram (2D) of most active antifungal compounds (p3 and p6) and standard fluconazole
Fig. 8
Fig. 8
Pictorial presentation (3D) and ligand interaction diagram (2D) of most active compound (p2) and standard 5-fluorouracil
Fig. 9
Fig. 9
Structural activity relationship of synthesized thiazole derivatives
See this image and copyright information in PMC

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