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Cai's Laboratory

Qian Cai, Ph.D.,
Principle Investigator

Dr. Qian Cai received his B.S. degree in chemistry from the department of chemistry, Nankai University in 2001 and his Ph.D. degree in Organic Chemistry from Shanghai Insittute of Organic Chemistry, Chinese Academy of Sciences in 2006. He then did his postdoctoral research in Medical School, University of Michigan, Ann Arbor under the supervision of Prof. Dr. Shaomeng Wang. Dr Cai joined GIBH in 2009 as an associate investigator and then was promoted as a principle investigator in the institute of chemical biology in 2010.
Dr Cai’s research is mainly focused on the development of novel synthetic methodology for the synthesis of biologically important heterocyclic compounds, design and synthesis of small molecules for carcer treatment. He has published more than 20 papers in Angew. Chem. Int. Ed., Acc. Chem. Res., J. Med. Chem., Org. Lett., Chem. Commun., Chem.-Eur. J., etc.

Graduate Students: Fengtao Zhou, Jiajie Yan, Xu Yan
Research Assistants: Jianguang Liu, Haoqiang Liang, Dan Liu, Yongtao Gao.

1) Novel Reactions for the synthesis of Heterocyclic Compounds:

2) Construction of Libraries of Anti-Cancer Small Molecule Drugs in Clinic Trails.
In order to offer support for anti-cancer drug discovery, we chose important small molecules under clinical trials for cancer treatment to construct small libraries. Now we have synthesized and collected more than 150 compounds in our libraries, which can be used as positive control in anti-cancer drug discovery. 

1. Zhou, Fengtao; Ding, Ke*; Cai, Qian. * Palladium-Catalyzed Amidation of N-Tosylhydrazones with Isocyanides. Chem. -Eur. J. 2011, chem.201102459.
2. Zhou, Fengtao; Fu, Liangbing; Wei, Jiajia; Ding, Ke; Cai, Qian.* Synthesis of 4-Oxo-indeno[1,2-b]pyrroles through Copper-Catalyzed Tandem Reactions of 1-(2-Haloaryl) enones with Isocyanides. Synthesis, 2011, 3037.
3. Gao, Mingshan; Liu, Xiujie; Wang, Xianyang; Cai, Qian*; Ding, Ke*. Synthesis of 1-Aryl-1H-indazoles via a Ligand-Free Copper-Catalyzed Intramolecular Amination Reaction. Chin. J. Chem. 2011, 29, 1199.
4. Zhou, Fengtao; Liu, Jianguang; Ding, Ke; Liu, Jinsong; Cai, Qian*. Copper-Catalyzed Tandem Reaction of Isocyanides with N-(2-Haloaryl)propiolamides for the Synthesis of Pyrrolo[3,2-c]quinolin-4-ones. J. Org. Chem. 2011, 76, 5346.
5. Cai, Qian; Sun, Haiying; Peng, Yuefeng, Lu, Jianfeng; Nikolovaks-Coleska, Zaneta; McEachern, Donna; Liu, Liu; Qiu, Su; Yang, Chao-Yie; Miller, Rebecca; Yi, Han; Zhang, Tao; Sun, Duxin; Kang, Sanmao; Guo, Ming; Leopold, Lance; Yang, Dajun; Wang, Shaomeng. A Potent and Orally Active Angagonist (SM-406/AT-406) of Multiple Inhibitor of Apoptosis Proteins (IAPs) in Clinical Development for Cancer Treatment. J. Med. Chem. 2011, 54, 2714.
6. Cai, Qian*;Zhou, Fengtao; Xu, Tianfeng; Fu, Liangbing; Ding, Ke*. Copper-Catalyzed Tandem Reactions of 1-(2-Iodoary) -2-yn-1-ones with Isocyanides for the Synthesis of 4-Oxo-indeno[1,2-b]pyrroles. Org. Lett. 2011, 13, 340.
7. Cai, Qian*; Li, Zhengqiu; Wei, Jiajia; Fu, Liangbin; Ha, Chengyong; Pei, Duanqing ; Ding, Ke*. Synthesis of Aza-Fused Polycyclic Quinolines through Copper-Catalyzed Cascade Reactions Org. Lett. 2010, 12, 1500.
8. Li, Zhengqiu; Fu, Liangbing; Wei, Jiajia; Ha, Chengyong; Pei, Duanqing; Cai, Qian*; Ding, Ke*. A Room-Temperature Copper-Catalyzed Cascade Process for Diethyl 2-Aryl-3,4-dihydro-4-oxo-1,1(2H)naphthalenedicarboxylate. Synthesis, 2010, 3289.
9. Cai, Qian*; Li, Zhengqiu; Wei, Jiajia; Ha, Chengyong; Pei, Duanqing ; Ding, Ke. Assembly of Indole-2-Carboxylic Acid Esters through a Ligand-Free Copper-Catalysed Cascade Process. Chem. Commun. 2009,7581.
10. Wang, Deping; Cai, Qian; Ding, Ke. An Efficient Copper-Catalyzed Amination of Aryl Halides by Aqueous Ammonia. Adv. Synth. Catal. 2009, 351, 1722.
11. Cai, Qian; Zhang, Hui; Zou, Benli; Xie, Xiaoan; Zhu, Wei; He, Gang; Wang, Jing; Pan, Xianhua; Chen, Yu; Yuan, Qiliang; Liu, Feng; Lu, Biao; Ma, Dawei. Amino Acid-Promoted Ullmann-type Coupling Reactions and Their Applications in Organic Synthesis. Pure Appl. Chem. 2009, 81, 227.
12. Ma, Dawei; Cai, Qian. Copper/Amino Acid Catalyzed Cross-Couplings of Aryl and Vinyl Halides with Nucleophiles. Acc. Chem. Res. 2008, 41, 1450.
13. Sun, Haiying; Nikolovska-Coleska, Zaneta; Yang, Chao-Yie; Qin, Dongguang; Lu, Jianfeng; Qiu, Su; Bai, Longchuan; Peng, Yuefeng; Cai, Qian; Wang, Shaomeng. Design of Small-Molecule Peptidic and Nonpeptidic Smac Mimetics. Acc. Chem. Res. 2008, 41, 1264.
14. Peng, Yuefeng; Sun, Haiying; Nikolovska-Coleska, Zaneta; Qiu, Su; Yang, Chao-Yie; Lu, Jianfeng; Cai, Qian; Yi, Han; Kang, Sanmao; Yang, Dajun; Wang, Shaomeng. Potent, Orally Bioavailable Diazabicyclic Small-Molecule Mimetics of Second Mitochondria-Derived Activator of Caspases. J. Med. Chem. 2008, 51, 8158.
15. Cai, Qian; Zou, Benli; Ma, Dawei. Mild Ullmann-type biaryl ether formation reaction via Combination of ortho-substituent and ligand effects. Angew. Chem. Int. Ed. 2006, 45, 1276.
16. Cai, Qian; He, Gang; Ma, Dawei. Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives. J. Org. Chem. 2006, 71, 5268.
17. Cai, Qian; Zhu, Wei; Zhang, Hui; Zhang, Yongda; Ma, Dawei. Preparation of N-Aryl compounds by Amino Acid-Promoted Ullmann-Type Coupling Reactions. Synthesis 2005, 03, 496.
18. Zhang, Hui; Cai, Qian; Ma, Dawei. Amino Acid Promoted CuI-Catalyzed C-N Bond Formation between Aryl Halides and Amines or N-Containing Heterocycles. J. Org. Chem. 2005, 70, 5164.
19. Ma, Dawei; Cai, Qian; Xie, Xiaoan. CuI/N,N-Dimethylglycine-Catalyzed Cross-Coupling Reaction of Vinyl Halides with Phenols and its Application to the Assembly of Substituted Benzofurans Cross-Coupling Reaction. Synlett 2005, 11, 1767.
20. Ma, Dawei; Cai, Qian. L-Proline Promoted Ullmann-Type Coupling Reactions of Aryl Iodides with Indoles, Pyrroles, Imidazoles or Pyrazoles. Synlett 2004, 01, 129.
21. Pan, Xianhua; Cai, Qian; Ma, Dawei. CuI/N,N-Dimethylglycine-Catalyzed Coupling Halides with Amides or Carbamates. Org. Lett. 2004, 6, 1809.
22. Ma, Dawei; Cai, Qian. N,N-Dimethyl Glycine-Promoted Ullmann Coupling Reaction of Phenols and Aryl Halides. Org. Lett. 2003, 5, 3799.
23. Ma, Dawei; Cai, Qian; Zhang Hui. Mild Method for Ullmann Coupling Reaction of Amines and Aryl Halides. Org. Lett. 2003, 5, 2453.

1. Wang, Shaomeng; Peng, Yuefeng; Sun, Haiying; Cai, Qian; Nikolovska-coleska, Zaneta; Lv, Jianfeng; Qiu, Su. Preparation of diazo bicyclic conformationally constrained Smac peptide mimetics as inhibitors of IAP proteins and inducers of apoptosis. WO 2008128171.
2. Wang, Shaomeng; Sun, Haiying; Qin, Dongguang; Nikolovska-Coleska, Zaneta; Lv, Jianfeng; Qiu, Su; Peng, Yuefeng; Cai, Qian. Bivalent Smac Mimetics and the Uses Thereof. WO 2007130626.
3. Ma, Dawei; Cai, Qian. Process for preparation of diaryl ethers with amino acid as additive. Faming Zhuanli Shenqing Gongkai Shuomingshu 2003, CN 1462735 A 20031224.
4. Ma, Dawei; Cai, Qian. Copper catalyzed N-Arylation or organic amines with amino acids as catalyst additive. Faming Zhuanli Shenqing Gongkai Shuomingshu 2003, CN 1450049 A 20031022.

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