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. 2018 Aug 12;12(1):92.
doi: 10.1186/s13065-018-0459-5.

Benzoxazole derivatives: design, synthesis and biological evaluation

Saloni Kakkar  1 , Sumit Tahlan  1 , Siong Meng Lim  2   3 , Kalavathy Ramasamy  2   3 , Vasudevan Mani  4 , Syed Adnan Ali Shah  2   5 , Balasubramanian Narasimhan  6
Affiliations

Benzoxazole derivatives: design, synthesis and biological evaluation

Saloni Kakkar et al. Chem Cent J. .

Abstract

Background: A new series of benzoxazole analogues was synthesized and checked for their in vitro antibacterial, antifungal and anticancer activities.

Results and discussion: The synthesized benzoxazole compounds were confirmed by IR, 1H/13C-NMR, mass and screened for their in vitro antimicrobial activity against Gram-positive bacterium: Bacillus subtilis, four Gram-negative bacteria: Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi and two fungal strains: Candida albicans and Aspergillus niger using tube dilution technique and minimum inhibitory concentration (MIC) was noted in µM and compared to ofloxacin and fluconazole. Human colorectal carcinoma (HCT116) cancer cell line was used for the determination of in vitro anticancer activity (IC50 value) by Sulforhodamine B assay using 5-fluorouracil as standard drug.

Conclusion: The performed study indicated that the compounds 1, 10, 13, 16, 19, 20 and 24 had highest antimicrobial activity with MIC values comparable to ofloxacin and fluconazole and compounds 4, 6, 25 and 26 had best anticancer activity in comparison to 5-fluorouracil.

Keywords: Anticancer; Antimicrobial; Benzoxazole; Characterization; Synthesis.

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Figures

Fig. 1
Fig. 1
Marketed drugs containing benzoxazole
Fig. 2
Fig. 2
Design of benzoxazole molecules for antimicrobial and anticancer potential based on literature
Scheme 1
Scheme 1
Synthesis of 2-(2-((benzo[d]oxazol-2-ylthio)methyl)-1H-benzo[d]imidazol-1-yl)acetohydrazide derivatives
Fig. 3
Fig. 3
Antibacterial screening results against Gram positive and Gram negative species
Fig. 4
Fig. 4
Antifungal screening results against fungal species
Fig. 5
Fig. 5
Structure activity relationship of the synthesized compounds
See this image and copyright information in PMC

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