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Ganem wins national award for cancer drug synthesis
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Ganem wins national award for cancer drug synthesis
Ganem wins national award for cancer drug synthesis

Ganem

Bruce Ganem, Cornell's Franz and Elisabeth Roessler Professor of Chemistry and J. Thomas Clark Professor of Entrepreneurship, is the winner of the American Chemical Society's (ACS) 2007 Award for Creative Invention. The award recognizes "the successful application of research in chemistry and/or chemical engineering that contributes to the material prosperity and happiness of people."

Ganem, who specializes in synthetic organic chemistry, solved a crucial problem in the production of paclitaxel, one of the most successful drugs used to treat ovarian, breast and lung cancer and a promising agent in fighting coronary artery disease.

First approved for ovarian cancer in 1992, paclitaxel (sold by BristolMyers Squibb under the brand-name Taxol) was initially extracted from the endangered and slow-growing Pacific yew tree. Major environmental concerns led researchers in France and Florida to devise a way of synthesizing the compound from the less-threatened English yew tree -- but that method involved a lengthy process and relied on a tree whose supply was also limited.

At Cornell, Ganem developed a new method for selectively reducing amide bonds, which are common in proteins, without affecting other reactive chemical bonds. Ganem helped Natural Pharmaceuticals, a Massachusetts start-up company, use that process to convert mixtures of taxanes extracted from the ornamental yew tree -- a prolific, fast-growing cousin of the Pacific and English yews -- into paclitaxel.

Ganem will be featured in Chemical and Engineering News in early 2007 and will be honored at the 233rd ACS National Meeting in Chicago in March.

Ganem joined the Cornell faculty in 1974; he is also active in Cornell's entrepreneurship program and has founded or co-founded several biopharmaceutical companies.

http://www.news.cornell.edu/stories/Sept06/ganem.acs.html

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Bruce  Ganem      

Title: Franz and Elisabeth Roessler Professor and J. Thomas Clark Professor of Entrepreneurship and Personal Enterprise
Office: 330 Baker Laboratory
Phone:          
(outside the University
preceded by 1-607-25)
 
5-7360
Email: bg18@cornell.edu

Educational Background:


PhD, Columbia University, 1972

BA, Harvard University, 1969


Awards:


•Alfred P. Sloan Research Foundation Fellow
•John Simon Guggenheim Memorial Foundation Fellow
•Camille and Henry Dreyfus Teacher-Scholar Award
•Eli Lilly Young Scientist Award
•American Cyanamid Award for the Advancement of the Art and Science of Chemical Synthesis
•Clark Distinguished Teaching Award
•Chemical Manufacturers Association National
•ACS Arthur C. Cope Scholar Award, 1996
•Catalyst Award, 1999


Research Description:



<--Element not supported - Type: 8 Name: #comment--><--Element not supported - Type: 8 Name: #comment-->SOCR
Synthetic Organic Chemistry Rules!


The research in our group focuses on modern applications of synthetic organic chemistry to a wide range of problems of biological interest. For example, we're interested in improving how modern diversity-oriented synthesis can be improved and enhanced. The use of combinatorial chemistry to create vast libraries of small molecules for drug discovery and development depends critically on effective methods for making complex structures in relatively few synthetic steps. Multiple component condensation (MCC) reactions such as the Ugi, Passerini, and Mannich reactions are particularly effective at building functionalized, drug-likes tructures from different families of compounds in a single step. Such processes are quite rare in chemistry (you can count the known MCC reactions on your fingers and toes), and we believe that inventing and developing new ones is an important pursuit in academic chemistry. The figure below depicts just a few of the novel one-pot MCC reactions that have been developed recently by our group to transform simple carbonyl compounds to pharmaceutically interesting structures.



We're also interested in the design and synthesis of small molecule mimics of monosaccharides and other carbohydrate derivatives. Novel photochemistry of heteroaromatics like pyridinium and pyrylium salts in acetonitrile provides a fertile source of interesting reactions that lead to highly functionalized cyclopentanes and cyclopentanone derivatives in one or two operations, as shown below.

Our group has also developed ways to create high densities of polymer brushes anchored on solid supports in a spatially addressable fashion. Such methodology could be used to immobilize organic compounds for controlled drug delivery (say, on drug-eluting cardiac stents) or for combinatorial chemistry and high-throughput screening or trace analyte detection. Such polymer brushes can be synthesized by a surface initiated ring opening metathesis polymerization (ROMP) reaction, and patterned by e-beam lithography, as shown in the AFM image below, for site-specific anchoring of drugs or other biological effectors.


Selected Publications:


G. Zhao, U. C. Deo, B. Ganem, "Selective Fowler Reductions: Asymmetric Total Syntheses of 1sofagomine and Other 1-Azasugars from Methyl Nicotinate," Org. Lett. 2001,        3, 201.      

M. A. Clark,, Q. Wang, B. Ganem, "Oxidation of Bicyclic Oxazolidines: Applications to Glycomimetics and Novel Saccharide Derivatives," Tetrahedron Lett. 2002, 43, 347.      

Q. Xia, B. Ganem, "An Efficient Synthesis of Substituted Prolines by the Selective Reduction and Reductive Cyanation of 2-Pyrrolidones," Tetrahedron Lett. 2002, 43, 1597.      

D. S. Hamilton, Z. Ding, B. Ganem, D. J. Creighton, "Glutathionyl Transferase-Catalyzed Addition of Glutathione to COMC: A New Hypothesis for Antitumor Activity," Org. Lett. 2002,        4, 1209.

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