Synthesis and anti-aging effect of SR9009 optical isomer
Objective To synthesize and study the anti-aging activity of the optical isomers of SR9009,a nuclear receptor Rev-Erbs agonist.Methods Using 5-nitrothiophene-2-carboxaldehyde,p-chlorobenzaldehyde and(S)-1-Boc-3-aminomethyl pyrrolidine or(R)-1-Boc-3-aminomethyl pyrrolidine as start materials,the optical isomers of SR9009 were synthesized through reductive amination reaction,deprotection of tert-butoxycarbonyl group and amide condensation reaction respectively.And then their anti-aging activities were tested using Caenorhabditis elegans model.Results SR9009 optical isomers were synthesized in four steps,and the total yield of(S)-isomer and(R)-isomer were 54.8%and 49.0%,respectively.In the experiment of C.elegans,(S)-isomer could significantly prolong the average lifespan of C.elegans by 7.8%.Conclusion The optical isomers of SR9009 and their synthetic methods are reported for the first time,and the(S)-isomer has anti-aging activity,which is worthy of further study.
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