"Synthesis, hepatotoxic evaluation and antipyretic activity of nitrate " by Madhurima Das, Surjyadipta Bhattacharjee et al.

Faculty Publications

Title

Synthesis, hepatotoxic evaluation and antipyretic activity of nitrate ester analogs of the acetaminophen derivative SCP-1

Authors

Madhurima Das, Department of Chemistry, University of New Orleans, New Orleans, LA 71048 USA.
Surjyadipta Bhattacharjee, Neuroscience Center of Excellence, Louisiana State University Health Science Center, New Orleans, LA 70112, USA.
Frank R. Fronczek, Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
Nicolas G. Bazan, Neuroscience Center of Excellence, Louisiana State University Health Science Center, New Orleans, LA 70112, USA.
Mark L. Trudell, Department of Chemistry, University of New Orleans, New Orleans, LA 71048 USA. Electronic address: mtrudell@uno.edu.

Document Type

Article

Publication Date

12-15-2018

Abstract

A series of nitrate ester analogues of the acetaminophen derivative SCP-1 were prepared by triflic acid catalyzed O-acylation of SCP-1 with chloroalkanoyl chlorides followed by nitration with silver nitrate. The chloroesters and corresponding nitrate esters were obtained in high yields. Preliminary hepatotoxicity studies revealed nitrate esters 5b (MD-38) and 5c (MD-39) to be well tolerated by human hepatocytes and had little effect on the three cytochrome P450 enzymes tested (CYP3A4, CYP2E1 and CYP2D6). In addition, the nitrate ester 5c (MD-39) exhibited antipyretic activity similar to acetaminophen.

Publication Source (Journal or Book title)

Bioorganic & medicinal chemistry letters

First Page

3798

Last Page

3801

Recommended Citation

Das, M., Bhattacharjee, S., Fronczek, F. R., Bazan, N. G., & Trudell, M. L. (2018). Synthesis, hepatotoxic evaluation and antipyretic activity of nitrate ester analogs of the acetaminophen derivative SCP-1. Bioorganic & medicinal chemistry letters, 28 (23-24), 3798-3801. https://doi.org/10.1016/j.bmcl.2018.09.020

This document is currently not available here.

COinS