Synthesis of chiral ND-322, ND-364 and ND-364 derivatives as selective inhibitors of human gelatinase.

@article{Yan2015SynthesisOC,
  title={Synthesis of chiral ND-322, ND-364 and ND-364 derivatives as selective inhibitors of human gelatinase.},
  author={Yugang Yan and Xueying Chen and Xinying Yang and Jian Zhang and Wenfang Xu and Yingjie Zhang},
  journal={Bioorganic & medicinal chemistry},
  year={2015},
  volume={23 20},
  pages={
          6632-40
        }
}
Compounds 10 (ND-322) and 15 (ND-364) are potent selective inhibitors for gelatinases, matrix metalloproteinase 2 (MMP2) and matrix metalloproteinase 9 (MMP9). However, both of them are racemates. Herein we report facile synthesis of optically active (R)- and (S)-enantiomers of compounds 10 and 15. And the sulfonyl of 15 was transformed to sulfinyl to obtain four epimeric mixtures. All synthesized thiirane-based compounds were evaluated in MMP2 and MMP9 inhibitory assays. Our results indicated… CONTINUE READING