Synthesis of novel chiral oxazolyl carbamates with good antibacterial activities and moderately effective anticancer properties

Background: Chiral oxazolines and chiral amino acids are two important classes of compounds that have been important in various fields and each has a wide range of different applications. Some of these applications are about biological studies such as antibacterial, antifungal and anticancer evaluations.Aim: In this paper, a new pathway for biological studies has been provided by the synthesis of new compounds from the binding of chiral amino oxazolines to chiral amino acids. A series of novel chiral (S, S)-oxazolyl carbamates were synthesized by reaction of (S)-N-protected α-amino acids and (S)-amino oxazolines.Methods: The structures of the novel chiral synthesized compounds were confirmed by spectral data and elemental analysis and then the antibacterial and antifungal activities of them were evaluated in vitro. The cytotoxic activities of these novel chiral oxazolyl carbamates derivatives (A-F) were investigated against one type of cancer cell line (Skove۳) and a non-cancerous cell line (HFF), at ۲۴ and ۷۲ hours after incubation using MTT assay Results: The MIC values shown that, in compounds containing protected phenyl alanine amino acid bonded to valine aminooxazoline and protected leucine amino acid bonded to valine aminooxazoline namely compounds ۵A and ۵B, respectively have a narrow range of antibacterial activity against gram positive bacteria Bacillus subtilis and Staphylococcus aureus. The novelty of the structure, on the one hand, and the structure of similar compounds, on the other, led us to try them again in another test. All compounds had cytotoxic effects on cancerous cell lines (Skove۳) especially on the time of ۷۲ h except the dose of ۰.۱µM, but cytotoxic effects of these compounds on normal cell line (HFF) were very lower except the dose of ۱۰۰۰µM which was toxic to normal cell too.Conclusion: In this study, we tried to introduce a new group of compounds including chiral oxazolines based on chiral amino acids to evaluate their biological effects. The remarkable point is that it is the first time that these compounds have been synthesized.

کلیدواژه ها:

(S ، S)-oxazoline carbamates ، (S)-amino oxazolines ، (S)-N-protected amino acids ، Antibacterial activity ، Anti cancer activities.