Abstract

In the proposed research, the chemistry of reactive electrophiles will be studied. This work involves both synthetic methodology development and mechanistic studies. In the development of new electrophilic synthetic methods, we will seek to apply the new chemistry to the preparation of biologically active compounds, including anti-depressant, anti-epileptic, analgesic, anti-psychotic, and anti-cancer drugs. The proposed research will lead to new methods for the preparation of commercial drugs, possibly leading to the more economical production of drugs. In the mechanistic studies, our work will provide insights to a variety of electrophilic reactions. Some of these mechanistic studies are directly related to biological systems, including NAD+ reduction, peptide cleavage reactions, acetylcholine chemistry, and electron transfer processes.

Public Health Relevance

Project Narrative This project will examine chemical structures and chemical reactions related to a number of important biochemical processes. The studies will also strive to invent new methodologies for the preparation of pharmaceutical substances.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Academic Research Enhancement Awards (AREA) (R15)
Project #
1R15GM085736-01A1
Application #
7646116
Study Section
Synthetic and Biological Chemistry A Study Section (SBCA)
Program Officer
Fabian, Miles
Project Start
2009-04-01
Project End
2013-03-31
Budget Start
2009-04-01
Budget End
2013-03-31
Support Year
1
Fiscal Year
2009
Total Cost
$217,500
Indirect Cost

  Institution

Name
Northern Illinois University
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
001745512
City
De Kalb
State
IL
Country
United States
Zip Code
60115

  Publications

Naredla, Rajasekhar Reddy; Klumpp, Douglas A (2013) Preparation of sulfonamides from N-silylamines. Tetrahedron Lett 54:5945-5947
Naredla, Rajasekhar Reddy; Raja, Erum K; Klumpp, Douglas A (2013) Preparation of Aryl-Susbstituted 2-Oxyindoles by Superelectrophilic Chemistry. Tetrahedron Lett 54:3245-3247
Naredla, Rajasekhar Reddy; Klumpp, Douglas A (2013) Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes. Tetrahedron 69:2137-2141
Tracy, Adam F; Abbott, Matthew P; Klumpp, Douglas A (2013) SUPERACID-PROMOTED HYDROXYALKYLATION OF 1,2-INDANDIONES. Synth Commun 43:2171-2177
Naredla, Rajasekhar Reddy; Klumpp, Douglas A (2013) Contemporary carbocation chemistry: applications in organic synthesis. Chem Rev 113:6905-48
Nilsson Lill, Sten O; Naredla, Rajasekhar Reddy; Zielinski, Matthew E et al. (2013) Dicationic ring-opening reactions of trans-2-phenylcyclopropylamine·HCl: electrophilic cleavage of the distal (C2-C3) bond of cyclopropanes. J Org Chem 78:8922-6
Zielinski, Matthew; Tracy, Adam F; Klumpp, Douglas A (2012) Utilization of the hydroxyalkylation reaction to prepare bis(benzocrown ethers). Tetrahedron Lett 53:1701-1704
Raja, Erum K; DeSchepper, Daniel J; Lill, Sten O Nilsson et al. (2012) Friedel-Crafts acylation with amides. J Org Chem 77:5788-93
Naredla, Rajasekhar Reddy; Klumpp, Douglas A (2012) Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine. Tetrahedron Lett 53:4779-4781
Kethe, Anila; Li, Ang; Klumpp, Douglas A (2012) Ring closing and opening reactions leading to aza-polycyclic aromatic compounds. Tetrahedron 68:3357-3360

Showing the most recent 10 out of 17 publications