Synthesis and Biological Evaluation of CF<sub>3</sub>Se‐Substituted α‐Amino Acid Derivatives
Zhou‐Zhou Han, Tao Dong, Xiao‐Xia Ming, Fu Kuang, Cheng‐Pan Zhang
Abstract
Abstract Several CF 3 Se‐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 ), (2 R ,3 R )‐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 [Me 4 N][SeCF 3 ]. 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 CF 3 Se‐substituted derivatives towards MCF‐7, HCT116, and SK‐OV‐3 cells, with their IC 50 values being less than 10 μM for MCF‐7 and HCT116 cells. This study indicated the potentials of CF 3 Se moiety as a pharmaceutically relevant group in the design and synthesis of novel biologically active molecules.