Benzoxazole derivatives: design, synthesis and biological evaluation

Abstract

BackgroundA new series of benzoxazole analogues was synthesized and checked for their in vitro antibacterial, antifungal and anticancer activities.Results and discussionThe 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.ConclusionThe 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.

Immunomodulatory and immunostimulatory effects of some bisbenzoxazole derivatives on lipopolysaccharide stimulated mammalian macrophages

“…The objective of the study was assessing the possible immunostimulatory and immunomodulatory effects of bisbenzoxazole based RHE 241 and 248 molecules on the unstimulated and LPS stimulated macrophages. Our results overlapped with the previous findings and these unique bisbenzoxazole derivatives significantly and substantially decreased the pro-inflammatory cytokine production by activated macrophages [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45]. This effect was so stark that the cytokine production was completely knockedout in the presence of our molecules.…”

“…This anti-proliferative function is partly due to their similarities to DNA bases [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45]. Benxoxazole derivatives probably interfere the DNA synthesis machinery and prevent cell proliferation in this way [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45]. Due to their strong biological activities benzoxazole derivatives have been suggested as anti-cancer and anti-inflammatory drugs [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45].…”

Cancer Metastasis: The Role of the Extracellular Matrix and the Heparan Sulfate Proteoglycan Perlecan

“…More recently, there has been the exploration of small molecular inhibitors of heparanase, that overcome these limitations, for example benzimidazole and benzoxazole derivatives (258)(259)(260). Benzimidazole and benzoxazole derivates have been long studied in medicinal chemistry (261). Most recent advances in these derivatives include the synthesis of symmetrical analogs that demonstrated superior anti-heparanase activity as compared to non-symmetrical analogs (240), with the ability to not only inhibit heparanase, but also bind and sequester HS interacting growth factors and chemokines that modulate angiogenesis.…”

More Than Resveratrol: New Insights into Stilbene-Based Compounds

“…Similar conclusions can be drawn from the structure−activity relationship (SAR) analysis for indole derivatives and several other aromatic groups [121]. The more interesting bicyclic compounds include benzoxazole derivatives [122]. For many years, the benzoxazole ring has been used in the design of biologically active molecules with the broad spectrum of biological activity, such as antiviral [123], antifungal [122], antibacterial [122] anticancer [122,124,125], and other activities [126].…”