James McKee PhD
James McKee PhD
Director, Graduate Programs in Chemistry, Biochemistry and Pharmacognosy
Professor of Chemistry
BS (University of Maryland)
PhD (University of Maryland)
Preparation and antibiotic activity of sulfonanilides and sulfones.
The use of the trihalomethyl group to prepare heterocyclic compounds such as hydantoins and iminohydantoins
Currently, my research is focused in two areas, (1) preparation and antibiotic activity of sulfonanilides and sulfones; and (2) the use of the trihalomethyl group to prepare heterocyclic compounds. Sulfonanilides and sulfones were amongst the earliest of the antibiotics and are still proving to be useful today, effectively treating such diseases as leprosy and epilepsy, as well as serving as general purpose antibiotics against all gram positive bacilli and all gram negative cocci. Currently, we are focusing on the development of sulfones and sulfonanilides that may be useful as anti-HIV agents. Unfortunately, the synthesis of these materials often involves multiple steps with low overall yields. We have developed a simple direct synthesis of this class of compounds, and are now concentrating on developing biologically active materials.
The second area of research is concerned with the use of the trihalomethyl group to prepare heterocycles, such as hydantoins and iminohydantoins. Materials of this class, such as dilantin, are potent antiepileptics and are currently used to treat seizures. The use of trihalomethylcarbinols and bidentate nucleophiles makes possible a facile synthesis of a great many interesting members of this class, compounds that would not be easily available by other routes.
Selected Scholarly Activity
“Synthesis of Tetrahydrobenzazepinesulfonamides and Their Rearrangement to Diarylsulfones,” H. Ren , M. Zanger, and J. R. McKee, Syn. Comm., 2006, 36, 355.
“The Synthesis of Iminohydantoins from Trihalomethylcarbinols,” J. A. McKee, J. R. McKee, and M. Zanger, 14th Annual St. Josephs University, Sigma Xi Research Symposium, April 11, 2003.
“The Electrophilic Bromation of Toluene: Determination of the ortho, meta and para Ratios by Quantitative FTIR Spectrometry,” R. Smith IV, J. McKee, and M. Zanger, J. Chem. Ed., 2002, 79, 227.
“A Microscale Synthesis of 2,3-Dibromosuccinic Acid,” J. Tomsho, M. Zanger, and J. McKee, J. Chem Ed., 1999, 76, 73. Small Scale Synthesis: A Laboratory Textbook of Organic Chemistry co-authored with M. Zanger, W.C. Brown Publishers, 1995.
Small Scale Synthesis: A Laboratory Textbook of Organic Chemistry co-authored with M. Zanger, W.C. Brown Publishers, 1995.
|Office location:||Robert McNeil Graduate Study and Research Center Room 201|
|Mailing address:||Box 48|
University of Sciences
600 South 43rd Street
Philadelphia, PA 19104-4495
j [dot] mckee [at] usciences [dot] edu