Synthesis of “neoprofen”, a rigidified analogue of ibuprofen, exemplifying synthetic methodology for altering the 3-D topology of pharmaceutical substances

Ron R. Ramsubhag; Chelsea L. Massaro; Christina M. Dadich; Andrew J. Janeczek; Tung T. Hoang; Elizabeth A. Mazzio; Suresh Eyunni; Karam F. A. Soliman; Gregory B. Dudley

doi:10.1039/C6OB01351A

Synthesis of “neoprofen”, a rigidified analogue of ibuprofen, exemplifying synthetic methodology for altering the 3-D topology of pharmaceutical substances

Ron R. Ramsubhag,^a Chelsea L. Massaro,^a Christina M. Dadich,^a Andrew J. Janeczek,^a Tung T. Hoang,^a Elizabeth A. Mazzio,^b Suresh Eyunni,^b Karam F. A. Soliman^b and Gregory B. Dudley*^a^c

Author affiliations

* Corresponding authors

^a Department of Chemistry and Biochemistry, Florida State University, Tallahassee, USA
E-mail: gdudley@chem.fsu.edu

^b College of Pharmacy and Pharmaceutical Sciences, Florida Agricultural and Mechanical University, Tallahassee, USA

^c C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, USA

Abstract

3,3-Dimethylcyclopentanes (neopentylenes) are ubiquitous in Nature but largely absent from synthetic pharmaceutical libraries. Neopentylenes define a hydrophobic and rigid 3-D topology with distinct molecular pharmacology, as exemplified here with two neopentylene-fused analogues of the synthetic anti-inflammatory drug, ibuprofen.

This article is part of the themed collection: Contemporary Synthetic Chemistry in Drug Discovery

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Publication details

The article was received on 22 Jun 2016, accepted on 01 Aug 2016 and first published on 01 Aug 2016

Article type: Communication

DOI: 10.1039/C6OB01351A

Citation: Org. Biomol. Chem., 2016,14, 7855-7858

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Synthesis of “neoprofen”, a rigidified analogue of ibuprofen, exemplifying synthetic methodology for altering the 3-D topology of pharmaceutical substances

R. R. Ramsubhag, C. L. Massaro, C. M. Dadich, A. J. Janeczek, T. T. Hoang, E. A. Mazzio, S. Eyunni, K. F. A. Soliman and G. B. Dudley, Org. Biomol. Chem., 2016, 14, 7855
DOI: 10.1039/C6OB01351A
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Ron R. Ramsubhag

Chelsea L. Massaro

Christina M. Dadich

Andrew J. Janeczek

Tung T. Hoang

Elizabeth A. Mazzio

Suresh Eyunni

Karam F. A. Soliman

Gregory B. Dudley

Organic & Biomolecular Chemistry

Synthesis of “neoprofen”, a rigidified analogue of ibuprofen, exemplifying synthetic methodology for altering the 3-D topology of pharmaceutical substances

Abstract

Supplementary files

Publication details

Synthesis of “neoprofen”, a rigidified analogue of ibuprofen, exemplifying synthetic methodology for altering the 3-D topology of pharmaceutical substances

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