Medicinal Chemistry
News and Events - 2008


September - November

Professor LaVoie served as a reviewer this summer of National Grant awarded by the Republic of Ireland through the Science Foundation of Ireland.
 
Professor LaVoie was nominated as a reviewer for presentations in Experimental Therapeutics at its National Meeting in 2009 by the Board of the American Association of Cancer Research.
 
Genzyme Corporation files IND for New TOP1-Targeting Drug for Cancer developed in Professor LaVoie’s laboratory.   

Xumu Zhang was awarded the Tech Pioneer Award by Suzhou Industrial Park,  P. R. China.

Professor Longqin Hu served on the 2008 Clinical and Experimental Therapeutics 4 (CET-4) Peer Review Panel for the DOD Breast Cancer Research Program in Reston, Virginia on July 13 – July 15, 2008.

Professor Longqin Hu received a grant from the National Institutes of Health/National Cancer Institute entitled “Homogenous HTS Assays to Screen for Inhibitors of Keap1-Nrf2 Interaction” for the period of 09/25/2008-07/31/2011.

Professor Xumu Zhang received funding from Dow Chemical Company for “Linear Selective Hydroformylation” for the period 9/08-9/10.

Sun, X.; Zhou, L.; Li, W.; Zhang, X. Convenient Divergent Strategy for the Synthesis of TunePhos-Type Chiral Diphosphine Ligands and Their Applications in Highly Enantioselective Ru-Catalyzed Hydrogenations. J. Org. Chem.,  2008, 73, 1143.

Yu, S.; Chie, Y.-M.; Guan, Zheng-hui; Zhang, Xumu. Highly Regioselective Isomerization-Hydroformylation of Internal Olefins to Linear Aldehyde Using Rh Complexes with Tetraphosphorus Ligands. Org. Lett., 2008, 10, 3469. 

Lu, Zheng; Zheng, Suqing; Zhang, Xumu; Lu, Xiyan. An Unexpected Phosphine-Catalyzed [3 + 2] Annulation. Synthesis of Highly Functionalized Cyclopentenes. Org. Lett., 2008, 10, 3267. 

Shang, G.; Zhang, X. Phospholes, phospholenes, phospholanes and phosphinanes. Ed: Boerner, A. in Phosphorus Ligands in Asymmetric Catalysis, 2008, 1, 135. 

Dai, Q.; Li, W.; Zhang, X. Development of a new class of C 1-symmetric bisphosphine ligands for rhodium-catalyzed asymmetric hydrogenation. Tetrahedron, 200864, 6943. 

Chen, J.; Liu, Q.; Zhang, W.; Spinella, S.; Lei, A.; Zhang, X. A Convenient Synthesis and the Asymmetric Hydrogenation of N-Phthaloyl Dehydroamino Acid Esters.  Org. Lett., 2008, 10, 3033. 

Xu, S.; Wang, Z.; Zhang, X.; Zhang, X.,Ding, K. Chiral Bronsted acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones by using aqueous H2O2. Angew. Chem. Int. Ed., 2008, 47, 2840.

Leslie S. Kurtzburg, Traci Battle, Cecile, Rouleau, Rebecca G. Bagley, Naoki, Agata, Min Yao, Steven Schmidt, Stephanie Roth, Jennifer Crawford, Roy Krumbholtz, Reginald Ewesuedo, Xian-Jie Yu, Fei Wang, Edmond J. LaVoie, Beverley A. Teicher, Bone marrow and tumor cell CFU and human xenograft efficacy of non-camptothecin and camptothecin topoiosmerase I inhibitors, Mol. Cancer Ther., 2008, 7, 3212-3222, .
 
Wei Feng, Mavurapu Satyanarayana, Liang Cheng, Angela A. Liu, Yuan-Chin Tsai, Leroy F. Liu and Edmond J. LaVoie, Synthesis of N-substituted 5-[2-(N-alkylamino)ethyl]dibenzo[c,h][1,6]naphthyridines as novel topoisomerase I-targeting antitumor agents, Bioorg. Med. Chem., 2008, 16, 9295-9301.
 
Wei Feng, Mavurapu Satyanarayana, Yuan-Chin Tsai, Angela A. Liu, Leroy F. Liu, and Edmond J. LaVoie,   11-Substituted 2,3-Dimethoxy-8,9-methylenedioxy-benzo[i]phenanthridine Derivatives as Novel Topoisomerase I-Targeting Antitumor Agents, Bioorg. Med. Chem., 2008, 16, 8598-8606.

Auemduan Prawan, Young-Sam Keum, Tin Oo Khor, Siwang Yu, Sujit Nair, Wenge Li, Longqin Hu, and Ah-Ng Tony Kong* Structural Influence of Isothiocyanates on the Antioxidant Response Element (ARE)-Mediated Heme Oxygenase-1 (HO-1) Expression. Pharm. Res., 2008, 25(4), 836-844.

Young-Sam Keum, Peter Pil-Jae Chang, Ki Han Kwon, Xiaoling Yuan, Wenge Li, Longqin Hu, and Ah-Ng Tony Kong* 3-Morpholinopropyl isothiocyanate (3MP-ITC) is a novel synthetic isothiocyanate that strongly induces the antioxidant response element (ARE)-dependent Nrf2-mediated detoxifying/antioxidant enzymes in vitro and in vivo. Carcinogenesis, 2008, 29(3), 594-599.

Professor Longqin Hu was invited to present a talk entitled “Novel Targeted Anticancer Prodrugs of Phosphoramide Mustard” at “Ehrlich II – 2nd World Conference on Magic Bullets” held on October 3 - 5, 2008, Nuremberg, Germany.

Professor Longqin Hu presented a seminar entitled “Novel Anticancer Prodrugs for Reductive and Proteolytic Activation” at Queen Mary, University of London, England, 10/07/2008 and at Cancer Research UK Institute for Cancer Studies, University of Birmingham, England, 10/06/2008.

Professor Xumu Zhang presented a seminar entitled “Advances in Asymmetric Hydrogenation Catalysis,  from Innovative Ligands to  Commercial Manufacture” Beijing,  The 4 th Sino-US Symposium on Organic Chemistry,  June 12, 2008.

Professor Xumu Zhang presented a seminar entitled “Development of Practical Asymmetric Hydrogenation and Hydroformylation Reactions” Organic Reactions & Processes Gordon Conference, Bryant University, Smithfield, RI,  July 14, 2008.

Professor Xumu Zhang presented a seminar entitled “Practical Asymmetric Hydrogenation and Hydroformylation Reactions” Stereochemistry Gordon Conference, Salve Regina University, Newport, RI, July 29, 2008.

Professor Xumu Zhang presented a seminar entitled “Practical Asymmetric Hydrogenation” Organometallic Chemistry Gordon Conference,  Salve Regina University, Newport, RI, July 8, The International Organic and  Pharmaceutical Meeting, Nanjing,  Oct. 15,The 15 th Chinese Organometallic Meeting, Nanjing,  Oct. 22, Beijing Institute of  Technology, Beijing,  Oct. 24, Chiba University,  Tokyo,  Japan, Nov. 4, Nippon Chemical Industrial Co. Ltd,  Tokyo,  Japan, Nov. 5, Tokyo University of Science,  Tokyo,  Japan, Nov. 5, Summit Pharmaceutical ,  Tokyo,  Japan, Nov. 6, Tokyo Institute of Technology ,  Tokyo,  Japan, Nov. 6, and at RIKEN (The Institute of Physical and Chemical Research),  Tokyo,  Japan, Nov. 7, 2008.

John J. Egan, Dilip Wagle, Sara Vasan, Martin Gall, Stanley Bell, and Edmond J. LaVoie, Method for treating glaucoma IC, US Patent 7,432,254, issued October 7, 2008.


August

The Graduate Program in Medicinal Chemistry is happy to welcome three new full-time incoming Ph.D. students:

Congratulations to the following students who recently graduated from the Medicinal Chemistry program:

Professor Longqin Hu served on the 2008 Clinical and Experimental Therapeutics 4 (CET-4) Peer Review Panel for the DOD Breast Cancer Research Program, Reston, VA, July 13-15, 2008.  

Yu Chen and Longqin Hu* Design of anticancer prodrugs for reductive activation. Med. Res. Rev.2008, Published Online: 7 Aug 2008.

Yongying Jiang and Longqin Hu* N-(2,2-Dimethyl-2-(2-nitrophenyl)acetyl)-4-aminocyclophosphamide as a potential bioreductively activated prodrug of phosphoramide mustard. Bioorg. Med. Chem. Lett., 2008, 18(14), 4059-4063.

Mavurapu Satyanarayana, Suzanne G. Rzuczek, Edmond J. LaVoie , Daniel S. Pilch, Angela Liu, Leroy F. Liu and Joseph E. Rice, Ring-Closing Metathesis for the Synthesis of a Highly G-Quadruplex Selective Macrocyclic Hexaoxazole Having Enhanced Cytotoxic Potency, Bioorg. Med. Chem. Lett., 18, 3802-3804, 2008.

Daniel S. Pilch, Christopher M. Barbieri, Suzanne G. Rzuczek, Edmond J. LaVoie and Joseph E. Rice, Targeting human telomeric G-quadruplex DNA with oxazole-containing macrocyclic compounds, Biochimie , 90, 1233-1249, 2008.

Mavurapu Satyanarayana, Wei Feng, Liang Cheng, Angela A. Liu, Yuan-Chin Tsai, Leroy F. Liu, and Edmond J. LaVoie, Syntheses and Biological Evaluation of Topoisomerase I-Targeting Agents Related to 11-[2-N,N-dimethylaminoethyl]-2,3-dimethoxy-8,9-methylenedioxy-11H -isoquino[4,3-c]cinnoline-12-one (ARC-31), Bioorg. Med. Chem., 16, 7824-7831, 2008.

Wei Feng, Mavurapu Satyanarayana, Yuan-Chin Tsai, Angela A. Liu, Leroy F. Liu, and Edmond J. LaVoie, Facile formation of hydrophilic derivatives of 5H -8,9-dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[ c,h][1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates, Bioorg. Med. Chem. Lett 18, 3570-3572, 2008.

Professor Longqin Hu presented a talk entitled “Design of Novel Anticancer Prodrugs for Site-Specific Activation and Delivery in Tumor Tissues” at The 4th Sino-US Chemistry, Professors Conference, June 12-13, 2008, Beijing, China.

Yu Chen, Kumar Pabbisetty , Dimitar Nikolov, and Longqin Hu Design and synthesis of peptidomimetics as potential EphB2 antagonists. Abstracts of Papers, 236 th ACS National Meeting, Philadelphia, PA, United States, August 17-21, 2008, MEDI-351.

Yiyu Ge, Xinghua Wu, Dazhi Zhang, Lin Chen, and Longqin Hu 3-Aminoxypropionate-based linker system for cyclization activation in prodrug design. Abstracts of Papers, 236 th ACS National Meeting, Philadelphia, PA, United States, August 17-21, 2008, MEDI-401.

Xinghua Wu, Yu Chen, and Longqin Hu A novel synthesis of chromogenic/fluorogenic amino acid conjugates of p-nitroaniline and 7-amino-4-methylcoumarin. Abstracts of Papers, 236 th ACS National Meeting, Philadelphia, PA, United States, August 17-21, 2008, ORGN-654.

Suzanne G. Rzuczek, Daniel S. Pilch, Angela Liu, Leroy F. Liu, Edmond J. LaVoie, and Joseph E. Rice Macrocyclic Polyoxazoles As Selective G-Quadruplex Stabilizers, 236th ACS National Meeting & Exposition, August 17-21, 2008, Philadelphia, PA, USA.

Mavurapu Satyanarayana, Suzanne G. Rzuczek, Daniel S. Pilch, Angela A. Liu, Leroy F. Liu, Edmond J. LaVoie, and Joseph E. Rice Ring-Closing Metathesis As An Entry Into Cytotoxic Macrocyclic Polyoxazoles, , 236th ACS National Meeting & Exposition, August 17-21, 2008, Philadelphia, PA, USA.

Wei Feng, Satyanarayana Mavurapu, Yuan-chin Tsai, Angela Liu, Leroy F. Liu, and Edmond J. LaVoie    11- and 12-Substituted 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine Derivatives as Novel Topoisomerase I-Targeting Antitumor Agents, , 236th ACS National Meeting & Exposition, August 17-21, 2008, Philadelphia, PA, USA.

Mavurapu Satyanarayana, Wei Feng, Liang Cheng, Angela A. Liu, Yuan-chin Tsai, Leroy F. Liu, Edmond J. LaVoie, Facile Formation of Hydrophilic Derivatives of 11-[2-(N,N-dimethylamino)-ethyl]-2,3-dimethoxy-8,9-methylenedioxy-11H-isoquino[4,3-c]cinnolin-12-one (ARC-31) and Its 11-Deaza Analog, ARC-111, , 236th ACS National Meeting & Exposition, August 17-21, 2008, Philadelphia, PA, USA.

Edmond J. LaVoie,Introduction to Natural Products Chemistry, Rutgers University International Training Program on Natural Products, New Brunswick, NJ USA August 11-15, 2008.

Edmond J. LaVoie,Biodisposition of Natural Products and GI Distress, Rutgers University International Training Program on Natural Products, New Brunswick NJ, USA, August 11-15, 2008.

LaVoie, E. J., Rice, J. E., Satyanarayana, M. , THERAPEUTIC COMPOUNDS, This application claims priority from U.S. Provisional Application Number 60/953660, filed 2 August 2007, which application is incorporated by reference.

LaVoie, E. J. and Rice, J. E., THERAPEUTIC COMPOUNDS, This application claims priority from U.S. Provisional Application Number 60/953648, filed 2 August 2007, which application is incorporated by reference.

February

Dr. Joseph Rice has been awarded a NCRR Shared Instrumentation Grant (SIG) in the amount of $351,400 for the Purchase of a 400 MHz Multi-Nuclear NMR Spectrometer to be housed in room 307. 

Professor Longqin Hu served on the Targeted Therapeutics 1 (TT-1) Peer Review Panel for the Komen for the Cure Foundation, Alexandria, VA, January 8-9, 2008.

Suzanne G. Rzuczek , Daniel S. Pilch, Edmond J. LaVoie, and Joseph E. Rice, Lysinyl Macrocyclic Hexaoxazoles: Synthesis and Selective G-Quadruplex Stabilizing Properties. Bioorganic and Medicinal Chemistry Letters, 18(3), 913-917, 2008.

Dr. Edmond J. LaVoie has been issued patent #7319105  on 1/15/08 for "Cytotoxic Agents"

January

Professor Xumu Zhang presented a talk at the Southwest Regional American Chemical Society meeting in Lubbock Texas, November 4-7, 2007.