title: Synthesis of "neoprofen", a rigidified analogue of ibuprofen, exemplifying synthetic methodology for altering the 3-D topology of pharmaceutical substances.
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.
authors: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA. gdudley@chem.fsu.edu.
authors: Ron R
authors: RR
authors: Ramsubhag
authors: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA. gdudley@chem.fsu.edu.
authors: Chelsea L
authors: CL
authors: Massaro
authors: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA. gdudley@chem.fsu.edu.
authors: Christina M
authors: CM
authors: Dadich
authors: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA. gdudley@chem.fsu.edu.
authors: Andrew J
authors: AJ
authors: Janeczek
authors: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA. gdudley@chem.fsu.edu.
authors: Tung T
authors: TT
authors: Hoang
authors: College of Pharmacy and Pharmaceutical Sciences, Florida Agricultural and Mechanical University, Tallahassee, Florida 32307, USA.
authors: Elizabeth A
authors: EA
authors: Mazzio
authors: College of Pharmacy and Pharmaceutical Sciences, Florida Agricultural and Mechanical University, Tallahassee, Florida 32307, USA.
authors: Suresh
authors: S
authors: Eyunni
authors: College of Pharmacy and Pharmaceutical Sciences, Florida Agricultural and Mechanical University, Tallahassee, Florida 32307, USA.
authors: Karam F A
authors: KF
authors: Soliman
authors: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA. gdudley@chem.fsu.edu and C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
authors: Gregory B
authors: GB
authors: Dudley
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051546:Cyclooxygenase 2 / Q000378:metabolism; D052246:Cyclooxygenase 2 Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007052:Ibuprofen / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D052246:Cyclooxygenase 2 Inhibitors; D051546:Cyclooxygenase 2; D007052:Ibuprofen