Jie Jack Li Research Lab

EDUCATION

 

MIT, Postdoctoral Fellow, 1995-1997, Professor Rick L. Danheiser

Indiana University, Ph.D., 1990-1995, Professor David R. Williams

Nanjing University, M. S., Nanjing, People’s Republic of China, 1984-1987

Nanjing University, B. S., Nanjing, People’s Republic of China, 1979-1983

 

TEACHING EXPERIENCE

 

·        Associate Prof., Organic and Medicinal Chemistry, University of San Francisco, 2013-present.

·        Assistant Prof., Organic Chemistry and Polymer Chemistry, Nanjing Forestry University, 1988-1990.

         Taught Introductory Organic Chemistry with over 100 students each academic year and supervised two Organic Laboratories; Taught        

         Polymer Chemistry for classes with over 100 students.

·        Teaching Assistant, Sophomore Organic Chemistry Laboratories, Indiana University, 1990-1992.

·        Teaching Assistant, Sophomore Organic Chemistry Laboratories, Nanjing University, 1984-1986.

 

INDUSTRIAL EXPERIENCE

 

Bristol-Myers Squibb Company

Sr. Research Investigator II, 2007-2012

Chemical Synthesis Group in Discovery Chemistry:

·        Worked at the interface of medicinal chemistry and process chemistry; scaling up of toxicology batches for drug candidates encompassing

         all therapeutic areas (TAs).  Completed targets in all therapeutic areas by leading a group of six chemists at times; 

·        Improved discovery routes for drug candidates (ECNs-Early Candidate Nominations);

·        Managed a group of eight chemists in BBRC in India for their efforts in prospective syntheses.

 

Pfizer Global Research and Development

Senior Principal Scientist, 1997-2007

·         Medicinal Chemist with more than ten years of experience in Inflammation, CNS, Dermatology, designed and worked on drugs for oral and           dermal applications as well as those crossing blood-brain barrier (BBB); 

·         Project leader since 2002 for teams staffing more than a dozen scientists at some stages of the projects, interacted positively with all                     disciplines including Molecular Biology, Pharmacology, PK/PD, Drug Safety, Patent Lawyers, and Clinical Development; Contributed to

          projects encompassing GPCRs (Smoothened, MCP-1, IL-8, and 5HT6), enzymes (MMPs, broad spectrum and MMP-13 specific), and    

          nuclear hormone receptors (AR and TR);  Significantly impacted TAs’ portfolio with delivery of drug candidates (MMP-13, TR, and AR) and 

          innovative proposals (e.g., HDACi for bipolar disorder and schizophrenia). One of my compounds is in Phase I (TR agonist);

 

PROFESSIONAL ACTIVITIES

 

Founding Executive Editorial Board Member, MedChemPharm24, Thieme: Germany, 2013-present

Volume Editor, Science of Synthesis, Volume 16 Updates, Six-Membered Hetarenes with Two Identical Heteroatoms, 2010-2012.

Expert Analyst and Guest Editor for ChemTracts, Organic Chemistry, 2002-2010

Editor, ARKIVOC, 2003-present

LIFE (Library Ideas and File Enrichment) Committee, 2002-2003, Pfizer

Chairman, Seminar Committee, 2000-2001, Pfizer

American Chemical Society, 1990-present

Ad hoc Referee for: Bioorganic and Medicinal Chemistry; Bioorganic and Medicinal Chemistry Letters; European Journal of Medicinal Chemistry; European Journal of Organic Chemistry ; Journal of American Chemical Society; Journal of Enzyme Inhibition and Medicinal Chemistry; Journal of Medicinal Chemistry; Journal of Natural Products; Journal of Organic Chemistry; MedChemComm; National Science Foundation (NSF); National Institute of Health (NIH); Organic Letters; Oxford University Press; Pathobiology; Romanian Research Council; Springer Verlag; Tetrahedron; Tetrahedron Letters; Wiley-VCH; Wiley

Recognized reviewer, Elsevier, 2014-present

 

AWARDS

 

The ROC Triumph Award, 2011, Bristol-Myers Squibb Company

R&D Star Award, 2011, Bristol-Myers Squibb Company

R&D Star Award, 2010, Bristol-Myers Squibb Company

R&D Star Awards, 2008, Bristol-Myers Squibb Company

Pfizer Employee Recognition Award, 2005

Neurontin Teamwork Award, 2004, Pfizer

Postdoctoral Fellowship, 1995-1997, MIT

Research Assistant, 1992-1995, Indiana University

Teaching Assistant, 1990-1992, Indiana University

Junior Faculty Teaching Award, 1988-1989, Nanjing Forestry University

Outstanding MS Thesis Award, 1988, Nanjing University

First-class Academic Achievement Scholarship, 1982-1983, Nanjing University

 

PUBLICATIONS

 

1.    Rhodium(III)-catalyzed C-H activation/[4+3] annulation of N-phenoxyacetamides and a,b-unsaturated aldehydes: anefficient route to 1,2-

       oxazepines at room temperature, Duan, P. P.; Lan, X.; Chen, Y.; Qian, S. S.; Li, J. J.; Lu, L.; Lu, Y.; Chen, B.; Hong, M.; Zhao, J. Chem.

       Commun. 2014, 50, 12135-12138.

2.    2,5-Bis-(Sulfonyl)pyrazines as Unprecedented Building Blocks and Their SNAr Reactions, Li, J. J.; Wei Meng, Shung Wu, Yong-Jin Wu,

       Jason Guernon, Michael M. Miller, Martin P. Allen, Peter T. Cheng, and Bang-chi Chen, Tetrahedron Lett. 2013, 54, 1938-1942.

3.    AlMe3-Promoted Formation of Amides From Acids and Amines, Li, J.; Subramaniam, K.; Smith, D.; Qiao, J. X.; Li, J. J.; Qian-Cutrone, J.;

       Kadow, J. F.; Vite, G. D.; Chen, B.-C. Org. Lett. 2012, 14, 214-217.

4.    Smoothened Antagonists for Hair Growth Inhibition, Jie Jack Li, Zenquan Wang, Veerabahu Shanmugasundaram, Bioorg. Med. Chem.

       Lett. 2010, 20, 4932-4935.

5.    Thyroid Receptor Agonists for the Treatment of Androgenetic Alopecia Li, J. J.; Mitchell, L. H.; Dow, R. L. Bioorg. Med. Chem.

        Lett. 2010, 20, 306-308.

6.     Rational Design and Synthesis of 4-((1R,2R)-2-Hydroxycyclohexyl)-2(trifluoromethyl)benzonitrile (PF-998425), A Novel, Non-steroidal

        Androgen Receptor Antagonist Devoid of Photo-toxicity for Dermatological Indications, Jie Jack Li, Donna M. Iula, Maria N. Nguyen, Lain-

        Yen Hu, Zhi Wang, Jennifer A. Van Camp, Theodore R. Johnson, William G. Harter, Wen-Song Yue, Mark L. Boys, Daniel Y. Du, Kimberly

        J. Wade, Matthew Carroll, Danielle Dettling, Brian M. Samas, Garrett S. Hoge, Mark J. Lovdahl, Jeffrey Asbill, Mary Ann Meade, Elena

        Spencer, Susan M. Ciotti, and Theresa Krieger-Burke J. Med. Chem. 2008, 51, 7010-7014.

7.     A Synthesis of N-Bridged 5,6-Bicylic Pyridines via A Mild Cyclodehydration Using the Burgess Reagent and Discovery of A Novel

        Carbamylsulfonylation Reaction, Jie Jack Li, James J. Li, Jun Li, Ashok K. Trehan, Henry S. Wong, Subramanian Krishnananthan, Lawrence

        J. Kennedy, Qi Gao, Alicia Ng, Jeffrey A. Robl, Balu Balasubramanian, and Bang-Chi Chen, Org. Lett.2008, 10, 2897-2900.

8.     Quinazolinones as Specific and Orally Active MMP-13 Inhibitors for the Treatment of Osteoarthritis, Li, J. J.; Yue, W.-S.; Ortwine, D. F.;

        Johnson, A. R.; Man, C.-F.; Baragi, V.; Kilgore, K.; Dyer, R. D.; Han, H.-K. J. Med. Chem. 2008, 51, 835-841.

9.     (1R,2S)-4-(2-Cyano-cyclohexyl-oxy)-2-trifluoromethyl-benzonitrile, A Potent Androgen Receptor Antagonist For Stimulating Hair Growth And

        Reducing Sebum Production, Lain-Yen Hu, Daniel Du, Jie Jack Li, et al. Bioorg. Med. Chem. Lett. 2007, 17, 5983-5988.

10.   Synthesis and Biological Evaluation of Amino-Pyridines As Androgen Receptor Antagonists For Stimulating Hair Growth And Reducing

        Sebum Production, Lain-Yen Hu, Huangshu John Lei,  Daniel Du, Theodore R. Johnson, Victor Fedij, Catherine Kostlan, Wen Song Yue,

        Mark Lovdahl, Jie Jack Li, Mathew Carroll, et al. Bioorg. Med. Chem. Lett. 2007, 17, 5693-5697.

11.    Preparation of 4-Aryl-2-Trifluoromethylbenzonitrile Derivatives As Androgen Receptor Antagonists For Topical Suppression of Sebum

         Production, Jennifer A. Van Camp, Lain-Yen Hu, Catherine Kostlan, Bruce Lefker, Jie Li, Lorna Mitchell, Zhi Wang, Wen-Song Yue,

         Matthew Carroll, Danielle Dettling, et al. Bioorg. Med. Chem. Lett. 2007, 17, 5529-5532.

12.    A Practical Buchwald-Hartwig Amination of 2-Bromopyridines with Volatile Amines, Li, J. J.; Wang, Z.; Mitchell, L. H. J. Org.

        Chem. 2007, 72, 3606-3607.

13.    SAR of 2-Amino-3-Heteroaryl-Quinoxalines As Potent, Non-Peptide Il-8 Receptor Antagonists, Jie Jack Li, Wen Song Yue, Bharat K.

         Trivedi, Steven R. Miller, David T. Connor, Bruce D. Roth, Joseph E. Low, David J. Heilig, Stephen Hunt,Kenneth G. Carson, Roberta A.

         Glynn, Qing Ye, Jay R. Luly, Weixing Yang, Shixin Qin Bioorg. Med. Chem. 2003, 11, 3777-3790.

14.    A Concise Synthesis of All Four Possible Benzo[4,5]furopyridines via Palladium-Mediated Reactions, Yue, W. S.; Li, J. J.Org.

         Lett. 2002, 4, 2201-2203.

15.    Stereoselective Synthesis of Syn- And Anti-1,3- And 1,2-Dimethyl Arrays Via Asymmetric Conjugate Additions, Williams, D. R.; Kissel, W.

          S.; Li, Jie Jack; Mullins, R. J. Tetrahedron Lett. 2002, 43, 3723-3727.

16.     Synthesis of Novel 3-Substituted Pyrrolo[2,3-b]quinoxalines via an Intramolecular Heck Reaction on an Aminoquinoxaline Scaffold, Li, J.

          J. J. Org. Chem. 1999, 64, 8425-8427.

17.     Synthesis of 3-Aryl and 3-Heterocyclic Quinoxalin-2-ylamines via Pd-Catalyzed Cross-Coupling Reactions, Li, J. J.; Yue, W. S. Tetrahedron

          Lett. 1999, 40, 4507-4510.

18.      Installation of 12b-Substitueuts onto Indolo[2,3-a]quinolizidin-2-ones and Application to Reserpone Analogue Synthesis, Li, J. J.; Trivedi,               B.K.; Rubin, J. R.; Roth, B. D. Tetrahedron Lett. 1998, 39, 6111-6114.

19.     Diastereoselection in The Conjugate Additions of Organocopper Reagents to N-Enoyoxazolidinones, Williams, D. R.; Kissel, W. S.; Li,

          J.J. Tetrahedron Lett. 1998, 39, 8593-8596.

20.      The Total Synthesis of Myxovirescin A1, Williams, D. R.; Li, J. Tetrahedron Lett. 1994, 35, 5113-5116.

21.      Gel Permeation Chromatography of Water-Soluble Lignosulfonates, Luo, L.; Wu, W.; Li, J.; Yu, S. Chromatography 1992,10, 375-376.

22.      Simultaneous Fermentation of Hemicellulosic Pentoses and Hexoses by Cadida Shehatae, Yu, S.; Luo, L.; Li, J.; Tang, H. Chemistry and

           Industry of Forestry Products 1991, 11, 17-24.

23.      Oxidation of Lignosulfonate to Vanillin, Luo, L.; Li, J.; Yu, S. Chemical Reaction and Engineering Technology 1990, 6, 53-59.

24.      Analysis of Acetic Acid, Furfural, and Ethanol in Spent Sulfite Liquor by Gas Chromatography, Li, J.; Luo, L.; Yu,

           S.Chromatography 1990, 8, 119-120.

25.      Pentose Fermentation of Spent Sulfite Liquor into Ethanol, Yu, S.; Luo, L.; Li, J. Industrial Microbiology 1989, 4, 23-27.

 

PATENTS

 

1.                Li, J.; Robl, J. A.; Li, J. J.; Kennedy, L. J.; Wang, H.; Li, J. J.; Qian, X.; Deshpande, R. P.; Kolla, L.R.; Cann, R. O.; Wei, C.; Galella,

                   M. Triazolopyridine 11-Beta Hydroxysteroid Dehydrogenase Type I Inhibitors. USP 8,119,658 (2012).

2.                Li, J.; Robl, J. A.; Li, J. J.; Kennedy, L. J.; Wang, H.; Li, J. J.; Qian, X.; Deshpande, R. P.; Kolla, L.R.; Cann, R. O.; Wei, C.; Galella,

                   M. Triazolopyridine 11-Beta Hydroxysteroid Dehydrogenase Type I Inhibitors. U.S. Pat. Appl. Publ. (2009), 86 pp. US 2009093516. 

3.                Jie Jack Li, Fused Tetrahydropyridine Derivatives as Inhibitors of Matrix Metalloproteinases, US6869958, May 22, 2004.

4.                Jie Jack Li, Substituted Naphthalene and Quinoline Derivatives as Inhibitors of Matrix Metalloproteinases WO20030803,

                   August 3, 2003.

5.                Gaudilliere, Bernard; Jacobelli, Henry; Kostlan, Catherine; Li, Jie Jack; Yue, Wen-song. Preparation of Oxo Azabicyclic Compounds

                   Such As Pyridopyrimidinones And Quinazolinones As Inhibitors Of Type-13 Matrix Metalloprotease. US6894057, June 8, 2003.

6.                William Harter, Jie Jack Li, Kevon Shuler, Wen-Song Yue; Fused Pyrimidinone Matrix Metalloproteinase InhibitorsWO200264598,

                   August 22, 2002.

7.                Dyer, Richard Dennis; Harter, William Glen; Hicks, James Lester; Johnson, Adam Richard; Li, Jie Jack; Roark, William Howard;

                   Shuler, Kevon Ray. Preparation of Bicyclic Pyrimidine Selective Mmp-13 Matrix Metalloproteinase Inhibitors With Therapeutic

                   Uses. WO200264599, August 22, 2002.

8.                Carson, Kenneth G.; Connor, David Thomas; Li, Jie Jack; Low, Joseph Edwin; Luly, Jay R.; Miller, Steven Robert; Roth, Bruce David;

                   Trivedi, Bharat Kalidas. Preparation of Substituted Quinoxaline Erivatives As Interleukin-8 Receptor Antagonists.WO9942463,

                   August 26, 1999.

9.                Connor, David Thomas; Li, Jie Jack; Low, Joseph Edwin; Miller, Steven Robert; Roth, Bruce David; Trivedi, Bharat Kalidas. 

                   Substituted Quinoxaline Derivatives As Interleukin-8 Receptor Antagonists. WO9942461, August 26, 1999. 

 

REVIEWS AND BOOK CHAPTERS

 

1.               Li, J. J. Chapter 6. Addition, Substitution, and Elimination Reactions in Organic Chemistry for Pharmacy; Renslo, A., ed.;

                  McGraw-Hill: Columbus, OH, 2014, in press.

2.               Li, J. J.; Johnson, A. R. Selective MMP13 Inhibitors, in Medicinal Research Review 2011, 30, 863-894.

3.               Brown, J. M.; Li, J. J.; Sinz, M. W. Antipsychotic Agents in Burger’s Medicinal Chemistry, Drug Discovery and Development, 7thed.,

                  Abraham, D. J.; Rotella, D. P., eds.; Wiley 2010, Vol. 8, pp. 161-218.

4.               1-Amino-4-benzylphthalazines as Orally Bioavailable Smoothened Antagonists With Antitumor Activity; Li,

                  J. J. Chemtracts 2010,23, 5-8. 

5.               Editorial by Li, J. J., Chemtracts 2008, 21(4), vii.

6.               Editorial by Li, J. J., Chemtracts 2008, 21(5), vii.

7.               Rationally Designed High-Affinity 2-Amino-6-Halopurine Heat Shock Protein 90 Inhibitors That Exhibit Potent Antitumor Activity Li,

                  Jie Jack Chemtracts 2007, 20, 262-266. 

8.               Li, J. J. Sommelet reaction, in Name Reactions for Functional Group Transformations, Jie Jack Li, Ed., Wiley: Hoboken, NJ, 2007, 

                  pp. 689-695. 

9.               Li, J. J. Hunsdiecker Reaction; in Name Reactions for Functional Group Transformations, Jie Jack Li, Ed., Wiley: Hoboken, NJ,

                  2007, pp. 623-629. 

10.             Advances in the Development of Methods For The Synthesis Of Neuraminidase Inhibitors For The Treatment Of Influenza [Oseltamivir

                  Phosphate (Tamiflu) and Zanamivir (Relenza)] Johnson, Douglas S.; Li, J. J., in The Art of Drug Synthesis Douglas S. Johnson,

                 Jie Jack Li, Eds., Wiley: Hoboken, NJ, 2007; pp. 95-114.

11.             An Introduction To Palladium Catalysis, Wolfe, John P.; Li, J. J., Tetrahedron Organic Chemistry Series (2007), 26(Palladium in

                  Heterocyclic Chemistry, (2nd Edition), pp.1-35.

12.             Sommelet Reaction, in Name Reactions for Functional Group Transformations, Jie Jack Li, Ed., Wiley: Hoboken, NJ, 2007,

                  pp. 689-695.

13.             Hunsdiecker Reaction, in Name Reactions for Functional Group Transformations, Jie Jack Li, Ed., Wiley: Hoboken, NJ, 2007,

                  pp. 623-629.

14.             Ramberg-Backlund Reaction. in Name Reactions for Functional Group Transformations, Jie Jack Li, Ed., Wiley: Hoboken, NJ, 2007,

                  pp. 386-404.

15.             Wacker-Tsuji Oxidation, in Name Reactions for Functional Group Transformations, Jie Jack Li, Ed., Wiley: Hoboken, NJ, 2007,

                  pp. 309-326.

16.             Wharton Reaction, in Name Reactions for Functional Group Transformations, Jie Jack Li, Ed., Wiley: Hoboken, NJ, 2007, pp.152-158.

17.             Design and Synthesis of 9-Octyl-Benzolactam-V9, A Selective Activator For Protein Kinase Ce and Ch Li, Jie Jack; Mitchell,

                  Lorna H. Chemtracts 2006, 19, 23-27. 

18.             The First Report of Selective Small Molecule Melanocortin-5 Receptor Antagonists Mitchell, Lorna H.; Li,

                  Jie Jack Chemtracts2005, 18, 226-229.

19.             Auwers Flavone Synthesis in Name Reactions in Heterocyclic Chemistry, Jie Jack Li, Ed., Wiley: Hoboken, NJ, 2005, pp.262-265.

20.             Hofmann-Loffler-Freytag Reaction, in Name Reactions in Heterocyclic Chemistry, Jie Jack Li, Ed., Wiley: Hoboken, NJ, 2005,

                  pp. 63-67.

21.             Hoch-Campbell Aziridine Synthesis, in Name Reactions in Heterocyclic Chemistry, Jie Jack Li, Ed., Wiley: Hoboken, NJ, 2005,

                  pp. 22-28.

22.             Corey-Chaykovsky Reaction, in Name Reactions in Heterocyclic Chemistry, Jie Jack Li, Ed., Wiley: Hoboken, NJ, 2005, pp. 2-14.

23.             Discovery of a New Class of Anilinoquinazoline Inhibitors with High Affinity and Specificity for the Tyrosine Kinase Domain of c-Src,

                  Jie Jack Li Chemtracts 2004, 17, 286-292.

24.             Jie Jack Li, 27.12, N-Haloimines, In Science of Synthesis, Houben-Weyl Methods of Molecular Transformations, Houben-Weyl,

                  Georg Thieme: Stuttgart-New York, 2004; Vol. 27, 499-510.

25.             Jie Jack Li, 27.14, Alkylideneazinic Acids and Derivatives, In Science of Synthesis, Houben-Weyl Methods of Molecular        

                  Transformations, Houben-Weyl, Georg Thieme: Stuttgart-New York, 2004; Vol. 27, 581-604.

26.             Jie Jack Li, 27.20, N-Nitroimines and N-Nitrosoimines, In Science of Synthesis, Houben-Weyl Methods of Molecular Transformations,

                  Houben-Weyl, Georg Thieme: Stuttgar -Ne