1,3-Diarylcycloalkanopyrazoles and diphenyl hydrazides as selective inhibitors of cyclooxygenase-2

Z Sui; J Guan; M P Ferro; K McCoy; M P Wachter; W V Murray; M Singer; M Steber; D M Ritchie; D C Argentieri

doi:10.1016/s0960-894x(00)00041-x

1,3-Diarylcycloalkanopyrazoles and diphenyl hydrazides as selective inhibitors of cyclooxygenase-2

Bioorg Med Chem Lett. 2000 Mar 20;10(6):601-4. doi: 10.1016/s0960-894x(00)00041-x.

Authors

Z Sui¹, J Guan, M P Ferro, K McCoy, M P Wachter, W V Murray, M Singer, M Steber, D M Ritchie, D C Argentieri

Affiliation

¹ The R.W. Johnson Pharmaceutical Research Institute, Raritan, NJ 08869, USA.

PMID: 10741562
DOI: 10.1016/s0960-894x(00)00041-x

Abstract

Novel 1,3-diarylcycloalkanopyrazoles 1, and diphenyl hydrazides 2 were identified as selective inhibitors of cyclooxygenase-2. The 1,3-diaryl substitution pattern of the pyrazole ring in 1 differentiates these compounds from most of the known selective COX-2 inhibitors that contain two aryl rings at the adjacent positions on a heterocyclic or a phenyl ring. Similarly, the two phenyl rings in 2 are also separated by three atoms. SAR of both phenyl rings in 1 and 2, and the aliphatic ring in 1 will be discussed.

MeSH terms

Azides / chemical synthesis*
Azides / pharmacology
Cyclooxygenase 1
Cyclooxygenase 2
Cyclooxygenase 2 Inhibitors
Cyclooxygenase Inhibitors / chemical synthesis*
Cyclooxygenase Inhibitors / pharmacology
Humans
Isoenzymes / drug effects*
Membrane Proteins
Prostaglandin-Endoperoxide Synthases / drug effects*
Pyrazoles / chemical synthesis*
Pyrazoles / pharmacology
Structure-Activity Relationship

Substances

Azides
Cyclooxygenase 2 Inhibitors
Cyclooxygenase Inhibitors
Isoenzymes
Membrane Proteins
Pyrazoles
Cyclooxygenase 1
Cyclooxygenase 2
PTGS1 protein, human
PTGS2 protein, human
Prostaglandin-Endoperoxide Synthases