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*^ac

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* Corresponding authors

^a Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA
E-mail: gdudley@chem.fsu.edu

^b College of Pharmacy and Pharmaceutical Sciences, Florida Agricultural and Mechanical University, Tallahassee, Florida 32307, USA

^c C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, 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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https://doi.org/10.1039/C6OB01351A

Submitted

22 Jun 2016

Accepted

01 Aug 2016

First published

01 Aug 2016

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

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Communication

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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†

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

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