Xiaojun Yao

Publications (3)14.32 Total impact

• Article: Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N,N'-cyclic azomethine imines.

  Liang Hong, Ming Kai, Chongyang Wu, Wangsheng Sun, Gongming Zhu, Guofeng Li, Xiaojun Yao, Rui Wang
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  ABSTRACT: A new chiral bis-phosphoric acid bearing triple axial chirality was synthesized and applied to effect a highly enantioselective 1,3-dipolar cycloaddition reaction between N,N'-azomethine imines and methyleneindolinones for the creation of chiral spiro[pyrazolidin-3,3'-oxindoles] in excellent yields and selectivities. MS experiment and DFT calculation studies prompted us to propose a dual H-bond donor activation mode of bis-phosphoric acid which is different from the traditional phosphoric acid catalysis.
  Chemical Communications 04/2013; · 6.17 Impact Factor
• Article: Asymmetric inverse-electron-demand hetero-Diels-Alder reaction for the construction of bicyclic skeletons with multiple stereocenters by using a bifunctional organocatalytic strategy: an efficient approach to chiral macrolides.

  Xianxing Jiang, Long Wang, Ming Kai, Liping Zhu, Xiaojun Yao, Rui Wang
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  ABSTRACT: We have performed the first bifunctional organocatalytic highly enantioselective inverse-electron-demand hetero-Diels-Alder reaction of cyclic ketones with enones to afford densely functionalized bicyclic skeletons that contain three stereocenters (up 82% yield, 10:1 d.r., and 97% ee). Unlike the previous IEDDAR catalytic strategy, this method features a double HOMO(dienophile)/ LUMO(diene)-activated pathway. Moreover, this process provides a promising method for the construction of enantioenriched macrolides.
  Chemistry 07/2012; 18(36):11465-73. · 5.93 Impact Factor
• Article: A new chiral 2-(ethylthio)-thiazolone analogue shows strong antitumor activities by inducing cancer cell apoptosis and inhibiting angiogenesis.

  Hongjin Song, Ming Kai, Xiaodong Liu, Wen Yin, Qian Zeng, Xiaojun Yao, Rui Wang
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  ABSTRACT: Our initial study showed the potent cytotoxic effects of a series of new chiral 2-(ethylthio)-thiazolone analogues we synthesized. In the present study, we used computer prediction and found that nitro functionality and the modification of substituents R could further improve their activities in the presence of the nitro group. Compound 1s with nitro, naphthyl, ethyl groups, and a chiral center was predicted to be the most effective. We showed that compound 1s could inhibit the growth of five different cancer cell lines in a time-dependent and dose-dependent manner. 1s could induce Hela cell apoptosis by activating the mitochondria apoptotic pathway. In addition, 1s could inhibit the proliferation, migration, tuber formation, and adhesion of human umbilical vein endothelial cells, suggesting its antiangiogenesis effects. Furthermore, we confirmed the in-vivo antitumor effects of 1s on sarcoma S-180-bearing mice. Taken together, chiral 2-(ethylthio)-thiazolone analogue 1s is a promising compound for further anticancer drug development.
  Anti-cancer drugs 05/2012; 23(9):914-22. · 2.23 Impact Factor