Major research fields: Methodology development for organic synthesis, medicinal chemistry, and pharmacology

1. Asymmetric synthesis methodology. In recent years, we have carried out systematic studies on the Lewis base catalyzed asymmetric reduction of imines by trichlorosilane for the asymmetric synthesis of chiral amines, for which the development of highly efficient and enantioselective new organocatalysts is our major focus. So far we have successfully developed five new types of catalysts that exhibited excellent enantioselectivities, which not only significantly expanded the categories of Lewis base catalysts, but also rendered the Lewis base catalyzed hydrosilylation a practically useful method with a broad substrate spectrum.

2. Medicinal Chemistry. We have developed a series of new angiotensin II receptor antagonists. Some novel synthetic methods towards the synthesis of nitrogen-containing drug molecules have also been developed using water phase reactions, microwave irradiations, and organocatalyses, etc., some of which have shown promising industrial application potentials.

3. Pharmacology. We are currently investigating the feasibility of developing secreted Wnt antagonists as new therapeutic agents targeting Wnt signaling pathway which has proven to be involved in tumorigenesis. We are also interested in developing novel apoptotic inducers and anticarcinogenic agents for cancer therapy and prevention from naturally occurring and synthetic organic compounds.

Group member introduction:

Professor Sun Jian, Ph.D.

Director of Natural Products Research Center

Chengdu Institute of Biology, Chinese Academy of Sciences

Email: sunjian@cib.ac.cn

Tel.: 86-28-85211220

Fax: 86-28-85222753

B.Sc., Sichuan University, China, 1998-1992

M.Sc., Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, China, 1992-1995

Ph.D., Institute of Chemistry, Chinese Academy of Sciences, China, 1995-1998

Research associate, The Scripps Research Institute, La Jolla, CA, USA, 1998-2001

Staff scientist, Sunesis Pharmaceuticals, Inc., South San Francisco, CA, USA, 2001-2004

Professor Lu Xiaoxia, Ph.D.

Chengdu Institute of Biology, Chinese Academy of Sciences

Email: luxx@cib.ac.cn

Tel.: 86-28-85253276

Fax: 86-28-85253276

B.Sc., Sichuan Normal College, China, 1990-1994

M.Sc., Sichuan University, China, 1994-1997

Ph.D., Sichuan University, China, 1997-2000

Research associate, The University of Hong Kong, Hong Kong, 2000-2004

Associate Professor Tang Yaxiong, Ph.D.

Natural Products Research Center

Chengdu Institute of Biology, Chinese Academy of Sciences

Email: tangyx@cib.ac.cn

Tel.: 86-28-85222768

Fax: 86-28-85222753

Ph.D., Genetics, Sichuan University, China, 2002

Professional experience:

2005-2008, Junior Specialist, University of California Irvine, CA, USA

2004-2005, Postdoctoral research fellow, University of Miami, Miami, USA

2003-2004, Postdoctoral research fellow, Memorial Sloan-Kettering Cancer Center, NY, USA

2000-2002, Research assistant, Institute of Microbiology, Chinese Academy of Sciences, China

1997-1999, Research assistant, Sichuan University, China

1993-1997, Engineer, Zhenjiang Pharmaceutical Corporation, China

Recent publications：

(1) Z. Lei, H. Li, Y. Li, X. Zhang, K, Chen, X. Wang, J. Sun, Z.-J. Shi, “Extrusion of CO from Aryl Ketones: Rhodium (I)-Catalyzed C-C Bond Cleavage Directed by a Pyridine Group”, Angew. Chem. Int. Ed. 2012, 51, 2609-2694.

(2) X. Cai, C. Wang, J. Sun, “Organocatalytic Enantioselective Dipolar [3+2] Cycloaddition of Acetylenic Aldehydes with Nitrones for the Formation of Chiral 4-Isoxazolines”, Adv. Synth. Catal. 2012, 354, 359-363.

(3) C. Wang, F. Xie, N. Suthiwangcharoen, J. Sun, Q. Wang, Tuning the optical properties of BODIPY dye through Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Sci. China Chem. 2012, 55, 125-130.

(4) X. Zhao, Y. Chao, P. Chen, D. Liu, P. Su, X. Cui, J. Sun, Y. Tang, “hRpn13, a newly identified component of 19S particle, regulates the proliferation, differentiation and function in human osteoblast-like cell line MG63”,Journal of Physiology and Biochemistry 2012, 689(1): 115-125, 139.

(5) X. Zhao, Y. Chao, Q. Wan, X. Chen, P. Su, J. Sun, Y. Tang, Flavokawain B induces apoptosis of human oral adenoid cystic cancer ACC-2 cells via up-regulation of Bim and down-regulation of Bcl-2 gene expression. Canadian Journal of Physiology and Pharmacology 2011, 89(12): 875-883.

(6) K. Cheng, T. Fan, J. Sun, “Chiral Phosphoric Acid Catalyzed Enantioselective Allylation of Aldehydes with Allyltrichlorosilane”, Chin. J. Chem. 2011, 29, 1669-1671.

(7) Y. Xiao, C. Wang, Y. Yao, J. Sun, Y.-C. Chen, “Direct Asymmetric Hydrosilylation of Indoles: Combined Lewis Base and Brønsted Acid Activation”, Angew. Chem. Int. Ed. 2011, 50, 10661-10664. Highlighted by SYNFACTS 2011, 12, 1360.

(8) X. Wu, Y. Li, C. Wang, L. Zhou, X. X. Lu, J. Sun, “Chiral Lewis Base Catalyzed Highly Enantioselective Reduction of N-Alkyl β-Enamino Esters with Trichlorosilane and Water”, Chem. Eur. J. 2011, 17, 2846-2848. Highlighted by SYNFACTS 2011, 12, 1360.

(9) Y. Li, K. Cheng, X. X. Lu, J. Sun, “A Facile and Efficient Approach to N-Protected-b-Sulfinylenamines via C-Sulfinylation of Enamides and Enecarbamates”, Adv. Synth. Catal. 2010, 352, 1876-1880.

(10)G. Kaur, C. Wang, J. Sun, Q. Wang, “The synergistic effects of multivalent ligand display and nanotopography on osteogenic differentiation of rat bone marrow stem cells”, Biomaterials 2010, 31, 5813-5824

(11)Z. Wang, Z. Li, X. X. Lu, J. Sun, “Chiral N-formyl amino alcohol as Lewis basic organocatalyst for enantioselective hydrosilylation of ketimines”, Chin. Sci. Bull. 2010, 55, 1726-1728.

(12)P. Wu, D. Lin, X. X. Lu, J. Sun, “Trimethylchlorosilane-promoted aza-Mannich Reaction of enecarbamates and aldimines”, Tetrahedron Lett. 2009, 50, 7249-7251.

(13)D. Lin, K. Cheng, X. X. Lu, J. Sun, “Methyltrichlorosilane/DMSO: A Facile and Highly Efficient Recipe for the Chlorination of Enamides and Enecarbamates”, Synlett 2009, (18), 2961-2964.

(14)P. Wu, Z. Wang, M. Cheng, L. Zhou, J. Sun, “Development of Highly Enantioselective New Lewis Basic N-Formamide Organocatalysts for Hydrosilylation of Imines with an Unprecedented Substrate Profile”, Tetrahedron 2008, 64, 11304-11312.

(15)C. Wang, X. Wu, L. Zhou, J. Sun, “A Highly Enantioselective Organocatalytic Method for Reduction of Aromatic N-Alkyl Ketimines”, Chem. Eur. J. 2008, 14, 8789-8792.

(16)D. Pei, Y. Zhang. S. Wei, M. Wang, J. Sun, “Rationally-Designed S-Chiral Bissulfinamides as Highly Enantioselective Organocatalysts for Reduction of Ketimines”, Adv. Synth. Catal. 2008, 350, 619-623. Highlighted by SYNFACTS 2008, 5, 0531.

(17)P. Wu, J. Sun, “Facile Allylation of N-Boc and N-Cbz Imines with Allyltrichlorosilane Promoted by DMF”, Syn. Commun. 2008, 38, 1003-1010.

(18)L. Zhou, Z. Wang, S. Wei, J. Sun, “Evolution of Chiral Lewis Basic N-Formamide as Highly Effective Organocatalyst for Asymmetric Reduction of Both Ketones and Ketimines with an Unprecedented Substrate Scope”, Chem. Commun. 2007, 2977 - 2979. Highlighted by Nature China.

(19)Z. Wang, S. Wei, C. Wang, J. Sun, “Enantioselective Hydrosilylation of Ketimines Catalyzed by Lewis Basic C₂-Symmetric Chiral Tetraamide”, Tetrahedron: Asymmetry 2007, 18, 705-709.

(20)H. Chen, Y. Wang, S. Wei, J. Sun, “L-Proline Derived Triamine as Highly Stereoselective Organocatalyst for Asymmetric Michael Addition of Cyclohexanone to Nitroolefins”, Tetrahedron: Asymmetry 2007, 18, 1308-1312.

(21)D. Pei, Z. Wang, S. Wei, Y. Zhang, J. Sun, “S-Chiral Sulfinamides as Highly Enantioselective Organocatalysts”, Org. Lett. 2006, 8(25), 5913-5915.Highlighted by SYNFACTS 2008, 5, 0531.

(22)Z. Wang, M. Cheng, P. Wu, S. Wei, J. Sun, “L-Piperazine-2-Carboxylic Acid Derived N-Formamide as Highly Enantioselective Lewis Basic Catalyst for Hydrosilylation of N-Aryl Imines with an Unprecedented Substrate Profile”, Org. Lett. 2006, 8(14), 3045-3048. Highlighted by Organic Chemistry Portal.

(23)Z. Wang, X. Ye, S. Wei, P. Wu, A. Zhang, J. Sun, “A Highly Enantioselective Lewis Basic Organocatalyst for Reduction of N-Aryl Imines with Unprecedented Substrate Spectrum”, Org. Lett. 2006, 8(5), 999-1001. Highlighted by Organic Chemistry Portal.

(24)C. Cheng, J. Sun, C. Wang, Y. Zhang, S. Wei, F. Jiang, Y. Wu, “Protonated N’-benzyl-N’-prolyl Proline Hydrazide as Highly Enantioselective Catalyst for Direct Asymmetric Aldol Reaction”, Chem. Commun. 2006, (2), 215 - 217.

(25)Y. Wang, S. Wei, J. Sun, “cis-4-Pyrrolidin-1-yl-L-Proline: A Highly Stereoselective Organocatalyst for the Direct Aldol Reaction”, Synlett 2006, (19), 3319-3323.

(26)C. Cheng, S. Wei, J. Sun, “Trans-4-Hydroxy-L-Proline Hydrazide-Trifluoroacetic Acid as Highly Stereoselective Organocatalyst for the Asymmetric Direct Aldol Reaction of Cyclohexanone”, Synlett 2006, (15), 2419-2422.

(27)X. Z. Guo, L. Shi, R.Wang, X. X. Liu, B. G. Li,X. X. Lu “Synthesis and biological activities of novel nonpeptide angiotensin II receptor antagonists based on benzimidazole derivatives bearing a heterocyclic ring”, Bioorg. Med. Chem. 2008, 16, 10301–10310。

(28)T. K. Huang, R. Wang, L. Shi,X. X. Lu, “Montmorillonite K-10: An efficient and reusable catalyst for the synthesis of quinoxaline derivatives in water”, Catal. Commun., 2008, 9, 1143–1147.

(29) R. Wang, T. K. Huang, L. Shi, B. G. Li, X. X. Lu, “Heteropoly Acids Catalyzed Direct Mannich Reactions: Three-Component Synthesis of N-Protected β-Amino Ketones”，Synlett 2007, 2197–2200.

(30)R. Wang, B. G. Li, T. K. Huang, L. Shi,X. X. Lu, “NbCl5-Catalyzed One-pot Mannich-type Reaction: Three Component Synthesis of β–Amino Carbonyl Compounds”,Tetrahedron Lett., 2007, 48, 2071–2073.

(31)R. Wang, X. X. Lu, X. Q. Yu, L. Shi, Y. Sun, “Acid-Catalyzed Solvent-Free Synthesis of 2-Arylbenzimidazoles under Microwave Irradiation”, J. Mol. Catal. A: Chem.,2007, 266, 198–201.