Dr. Andrew McPhail

Professor of Chemistry

email: atmcph@chem.duke.edu

phone: (919) 660-1552

office: 336 Gross Chem

Lab: Room 380 (919)660-1568

Ph.D. '63, Univ. of Glasgow; Asst. Lect. '61-'64, Univ. of Glasgow; Postdoctoral Res. Assoc. '64-'66, Univ. of Illinois; Lect. in Chemistry, '66-'68; Univ. of Sussex; Assoc. Prof. '68-'73, Prof. '73-, Director, X- Ray Structure Center '84-, Duke Univ.; Adjunct Prof. '83-, School of Pharm., UNC-Chapel Hill.

Research Interests

Physical and Structural Chemistry


Elucidation of molecular structures by single- crystal x-ray analysis has become more routine in recent years with the advent of high-speed computers and commercial data collection facilities so that it now ranks as a competitor to the more conventional spectroscopic methods.

Biologically active compounds, isolated from various sources (e.g. molds, plants, marine organisms), are often obtained in extremely small quantities which preclude the determination of their structures by conventional spectroscopic and chemical methods. For these compounds a single-crystal diffraction study is the most rapid and in some cases the only route to unequivocal determination of the complete structure and stereochemistry. In addition, detailed conformational analysis of such compounds makes an important contribution to our understanding of structure-activity relationships and the solid state conformation may be correlated with that in solution through the use of spectroscopic measurements. Other structural studies in progress involve examination of the detailed molecular geometries of simple heterocycles in crystals and the relationships of the parameters to other physical measurements.

A synthesis program is directed towards the preparation and structural characterization of a novel series of boron-containing analogues of a-amino acids, their peptide derivatives, and metal complexes; several of these compounds have been shown to possess interesting biological activity.



Selected Publications:

Wall, M. E., Wani, M. C., Fullas, F., Oswald, J. B., Brown, D. M., Santisuk, T., Reutrakul, V., McPhail, A. T., Farnsworth, N. R., Pezzuto, J. M., Kinghorn, A. D., and Besterman, J. M., "Plant Antitumor Agents. 31. The Calycopterones, a New Class of Biflavonoids with Novel Cytotoxicity in a Diverse Panel of Human Tumor Cell Lines," J. Med. Chem., 1994, 37, 1465-1470.
Zhang, S., Lee, C. T.-L., Chen, K., Kashiwada, Y., Zhang, D.-C., McPhail, A. T., and Lee, K.-H., "Structure and Stereochemistry of Taxuchin A, a New 11(15->1)Abeo-Taxane Type Diterpene from Taxus Chinensis," J. Chem. Soc., Chem. Commun., 1994, 1561-1562.
Wang, H.-K., Liu, S.-Y., Hwang, K.-M., McPhail, A. T., and Lee, K.-H., "Antitumor agents. 160. The Synthesis of 5-Substituted Camptothecins as Potential Inhibitors of DNA Topoisomerase I," Bioorg. Med. Chem. Lett., 1995, 5, 77-82.
Austin, R. N., Clark, T. J., Dickson, T. E., Killian, C. M., Nile, T. A., Schabacker, D. N., and McPhail, A. T. "Synthesis and Properties of Novel Substituted 4,5,6,7-Tetrahydroindenes and Selected Metal Complexes," J. Organomet. Chem., 1995, 491, 11-18.
Shi, Q., Chen, K., Li, L., Chang, J.-J., Autry, C., Kozuka, M., Konoshima, T., Estes, J. R., Lin, C. M., Hamel, E., McPhail, A. T., McPhail, D. R., and Lee, K.-H., "Antitumor Agents. 154. Cytotoxic and Antimitotic Flavonols from Polanisia dodecandra," J. Nat. Prod., 1995, 58, 475-482.
Zhang, S.-X., Chen, K., Liu, X.-J., Zhang, D.-C., Tao-Wiedmann, T.-W., Leu, S.-L., McPhail, A. T., and Lee, K.-H., "Isolation and Structural Elucidation of Three New Neolignans, Puberulins A, B, and C, from Piper puberulum, as Platelet Activating Receptor Antagonists," J. Nat. Prod., 1995, 58, 540-547.
Mossa, J. S., Muhammad, I., Al-Yahya, M. A., Mirza, H. H., El-Feraly, F. S., and McPhail, A. T., "Five New Modified 6,7-Secolabdane Diterpenoids from Cluytia richardiana," J. Nat. Prod., 1996, 59, 224-231.

Chen, K., Zhang, Y.-L., Li, Z.-L., Shi, Q., Poon, C.-D., Tang, R.-J., McPhail, A. T., and Lee, K.-H., "Structure and Stereochemistry of Pseudolarolide J, a Novel Nortriterpene Lactone from Pseudolarix kaempferi," J. Nat. Prod., 1996, 59, 1200-1202.

Muhammad, I., Mossa, J. S., Al-Yahya, M. A., El-Feraly, F. S., and McPhail, A. T., "Hypoestenone: a Fusicoccane Diterpene Ketone from Hypoestes forskalei," Phytochemistry, 1997, 44, 125-129.

Shi, Q., Verdier-Pinard, P., Brossi, A., Hamel, E., McPhail, A. T. and Lee, K.- H., "Antitumor Agents. 172. Synthesis and Biological Evaluation of Novel Deacetamidothiocolchicin-7-ols and Ester Analogs as Antitubulin Agents," J. Med. Chem., 1997, 40, 961-966.