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Synthesis and Biological Evaluation of CF3Se‐Substituted α‐Amino Acid Derivatives
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AbstractSeveral CF3Se‐substituted α‐amino acid derivatives, such as (R)‐2‐amino‐3‐((trifluoromethyl)selanyl)propanoates (5 a/6 a), (S)‐2‐amino‐4‐((trifluoromethyl)selanyl)butanoates (5 b/6 b), (2R,3R)‐2‐amino‐3‐((trifluoromethyl)selanyl)butanoates (5 c/6 c), (R)‐2‐((S)‐2‐amino‐3‐phenylpropanamido)‐3‐((trifluoromethyl)selanyl)propanoates (11 a/12 a), and (R)‐2‐(2‐aminoacetamido)‐3‐((trifluoromethyl)selanyl)propanoates (11 b/12 b), were readily synthesized from natural amino acids and [Me4N][SeCF3]. The primary in vitro cytotoxicity assays revealed that compounds 6 a, 11 a and 12 a were more effective cell growth inhibitors than the other tested CF3Se‐substituted derivatives towards MCF‐7, HCT116, and SK‐OV‐3 cells, with their IC50 values being less than 10 μM for MCF‐7 and HCT116 cells. This study indicated the potentials of CF3Se moiety as a pharmaceutically relevant group in the design and synthesis of novel biologically active molecules.
Title: Synthesis and Biological Evaluation of CF3Se‐Substituted α‐Amino Acid Derivatives
Description:
AbstractSeveral CF3Se‐substituted α‐amino acid derivatives, such as (R)‐2‐amino‐3‐((trifluoromethyl)selanyl)propanoates (5 a/6 a), (S)‐2‐amino‐4‐((trifluoromethyl)selanyl)butanoates (5 b/6 b), (2R,3R)‐2‐amino‐3‐((trifluoromethyl)selanyl)butanoates (5 c/6 c), (R)‐2‐((S)‐2‐amino‐3‐phenylpropanamido)‐3‐((trifluoromethyl)selanyl)propanoates (11 a/12 a), and (R)‐2‐(2‐aminoacetamido)‐3‐((trifluoromethyl)selanyl)propanoates (11 b/12 b), were readily synthesized from natural amino acids and [Me4N][SeCF3].
The primary in vitro cytotoxicity assays revealed that compounds 6 a, 11 a and 12 a were more effective cell growth inhibitors than the other tested CF3Se‐substituted derivatives towards MCF‐7, HCT116, and SK‐OV‐3 cells, with their IC50 values being less than 10 μM for MCF‐7 and HCT116 cells.
This study indicated the potentials of CF3Se moiety as a pharmaceutically relevant group in the design and synthesis of novel biologically active molecules.
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