FEATURED AUTHOR

Norma Dunlap

Professor
Middle Tennessee State University

Norma Dunlap is the author, with Donna Huryn, of Medicinal Chemistry, a textbook that gives an overview of the field of medicinal chemistry. She is a Professor at MTSU, where she teaches and does research in organic synthesis, mainly with undergraduates. In a former life, she was a researcher in drug discovery at Hoffmann-La Roche. A native of Philadelphia, Norma lives in Tennessee with her husband, as well as a dog and cats. She has two sons and a daughter, none of whom are chemists.

Subjects: Chemistry

Biography

Norma Dunlap’s interest in Organic Chemistry dates back to her undergraduate days at Eastern University, a small college near Philadelphia. Although she had an industrial job in Analytical Chemistry for several years post-B.S., she returned to graduate school to further her education in Organic, moving far out west to the University of Wyoming. Her research in organic synthesis there with Dave Watt led to a Post-doctoral fellowship in Amos Smith’s group at the University of Pennsylvania, after which she took a position as a research scientist at Hoffmann-LaRoche. Her work there was as a Medicinal chemist in drug discovery, in anti-bacterial research. After about five years at Roche, life intervened, and she moved with her husband and a new infant to Tennessee, both taking positions at Vanderbilt University. This is where she discovered a previously unknown love of teaching, and also began to develop a course on Medicinal Chemistry. Wanting to teach this from the perspective of a practicing Medicinal chemist, and not finding a suitable undergraduate text for a one-semester survey course, she began to develop what would become the Medicinal Chemistry textbook. After six years of teaching at Vanderbilt, she moved down the road to Middle Tennessee State University, where she is now Professor of chemistry. There, she has been teaching and carrying out research, primarily with undergraduates, since 1998.

Education

Areas of Research / Professional Expertise

Personal Interests

hiking, gardening, tennis

Books

Featured Title

Articles

Antitrypanosomal activity of iridals from Iris domestica

Published: Dec 01, 2016 by Phytochemistry Letters v. 18 p. 44-50
Authors: Anuradha Liyana Pathiranage, Jeannie Moore Stubblefield, Xiaolei Zhou, Jianhua Miao, Anthony L. Newsome, and Norma Dunla

The petroleum ether extract of Iris domestica (Belamcanda chinensis) has been evaluated for activity against Trypanosoma brucei. Bioassay-guided fractionation led to the isolation of four known iridals as the active components. Chemical modification of these isolates afforded novel stable derivatives that maintained bioactivity. This is the first known report of the antitrypanosomal activity of these compounds.

Synthesis and evaluation of ether-linked dimers of demethylepipodophyllotoxin

Published: Dec 15, 2014 by Bioorg. & Med. Chem. Letters 2014, 24, 5627-5629
Authors: N. Dunlap, T. L. J. Salyard, A. L. Pathiranage, J. Stubblefield, S. L. Pitts, R. E. Ashley, N. Osheroff

A series of novel ether-linked dimers of demethylepipodophyllotoxin are topoisomerase II poisons that exhibit higher levels of double-stranded versus single-stranded DNA cleavage than their corresponding monomers. The dimers also have higher levels of tumor cell cytotoxicity than the monomers, lending support to the two-drug model for interaction of demethylepipodophyllotoxins with human topoisomerase IIα.

Synthesis of cyclocaric acid A and comparison to material from Cyclocarya paliurus

Published: Nov 26, 2014 by J. Nat. Prod. 2014, 77, 2566-2569
Authors: M. E. Wright, J. Byrd, C. He and N. Dunlap

Components previously reported from Cyclocarya paliurus include the oleananes cyclocaric acid A and cyclocaric acid B, with cyclocaric acid A possessing an oxetane ring. Isolation of cyclocaric acid A from the plant extract and comparison to the literature report show that the compound originally reported as cyclocaric acid A is, in fact, hederagenin. Independent synthesis of the oxetane proved this to be true, and indicate that cyclocaric acid A may not actually be a natural product.

Synthesis of nitrocyclopropyl peptidomimetics

Published: Nov 27, 2013 by Tetrahedron Lett. 2013, 54, 6596-6598
Authors: N. K. Dunlap, J. Basham, M. Wright, K. Smith, O. Chapa, J. Huang, W. Shelton, Y. Yatsky

Nitrocyclopropanation of amino-acid derived enones has led to a series of cyclopropyl peptidomimetics suitable for further elaboration to compounds with the potential for biological activity.

Three-step synthesis of cyclopropyl peptidomimetics

Published: Aug 24, 2011 by Org. Lett. 2011, 13, 4879-4881
Authors: N. Dunlap, K. R. Lankford, A. L. Pathiranage, J. Taylor, N. Reddy, D. Gouger, P. Singer, K. Griffin and J. Reibenspies

An efficient approach to novel cyclopropyl peptidomimetics has been developed. The synthetic route involves a cyclopropanation using ethyl (dimethylsulfuranylidene)acetate (EDSA) as the key step and affords a cyclopropyl peptidomimetic core in three steps from protected amino acid Weinreb amides.

A Concise Synthesis of Enantiomers of 4-Aminobutane-1,2,3-triol

Published: Apr 04, 2008 by J. Org. Chem. 2008, 73, 2928-2930
Authors: N. K. Dunlap, J. Drake, A. Ward, T.L.J. Salyard and L. Martin

A very efficient synthesis of (2R,3S) and (2S,3R)-4-aminobutane-1,2,3-triol has been developed using either d- or l-glucose as the starting material. A key step is the one-pot conversion of an aldehyde to an amide, the scope of which has been extended to include other carbohydrate-derived aldehydes.

Substituents on Etoposide that Interact with Human Topoisomerase IIα in the Binary Enzyme-Drug Complex: Contributions to Etoposide Binding and Activity

Published: Mar 21, 2008 by Biochemistry 2008, 47, 4501-4509
Authors: R. P. Bender, M. J. Jablonsky, M. Shadid, I. Romaine, N. Dunlap, C. Anklin, D. E. Graves and N. Osheroff

The present study used DNA cleavage assays, saturation transfer difference [1H] NMR spectroscopy, and enzyme−drug binding studies to further define interactions between etoposide and human topoisomerase IIα. Etoposide and three derivatives that lacked the C4 sugar were analyzed.

Synthesis of a Highly Reactive 1,1-Dicyanomethylene-1-dethiacephalosporin

Published: Oct 27, 1992 by Tetrahedron Letters 1992, 6103
Authors: N. K. Dunlap, M. Dezube, D. D. Keith and M. Weigele

Synthesis of the 1,1-dicyanomethylene-1-dethiacephalosporin 1a is described. Substitution of the dicyanomethylene moiety for sulfur at position 1 of the cephem nucleus resulted in a highly reactive β-lactam antibacterial.

Dual-Action Penems and Carbapenems

Published: May 20, 1992 by J. Med. Chem. 1992, 35, 1828
Authors: A. J. Corraz, S. L. Dax, N. K. Dunlap, N. H. Georgopapadakou, D. D. Keith, D. L. Pruess, P. L. Rossman, R. Then, J. Unow

The antibacterial activity of quinolones occurs as a consequence of interaction with bacterial DNA gyrase, while beta lactams act via inhibition of peptidoglycan transpeptidase(s). By combining the two into a novel molecular hybrid, the result is inhibition of DNA replication and cell wall assembly.