Synthesis of 3-phenylpyrazolo[4,3-b]pyridines via a convenient synthesis of 4-amino-3-arylpyrazoles and SAR of corticotropin-releasing factor receptor type-1 antagonists

Keith Wilcoxen; Charles Q Huang; James R McCarthy; Dimitri E Grigoriadis; Chen Chen

doi:10.1016/s0960-894x(03)00621-8

Synthesis of 3-phenylpyrazolo[4,3-b]pyridines via a convenient synthesis of 4-amino-3-arylpyrazoles and SAR of corticotropin-releasing factor receptor type-1 antagonists

Bioorg Med Chem Lett. 2003 Oct 6;13(19):3367-70. doi: 10.1016/s0960-894x(03)00621-8.

Authors

Keith Wilcoxen¹, Charles Q Huang, James R McCarthy, Dimitri E Grigoriadis, Chen Chen

Affiliation

¹ Department of Medicinal Chemistry, Neurocrine Biosciences, Inc., 10555 Science Center Drive, San Diego, CA 92121, USA.

PMID: 12951127
DOI: 10.1016/s0960-894x(03)00621-8

Abstract

3-Phenylpyrazolo[4,3-b]pyridines were synthesized via a cyclization of 4-amino-3-phenylpyrazoles 11-13 with ethyl acetoacetate. These compounds were found to be potent CRF(1) antagonists. The 2-alkylpyrazolo[4,3-b]pyridines were more polar but less active than the corresponding 1-alkyl-isomers.

MeSH terms

Humans
Pyrazoles / chemical synthesis*
Pyrazoles / pharmacology
Pyridines / chemical synthesis*
Pyridines / pharmacology
Receptors, Corticotropin-Releasing Hormone / antagonists & inhibitors*
Receptors, Corticotropin-Releasing Hormone / metabolism
Structure-Activity Relationship

Substances

Pyrazoles
Pyridines
Receptors, Corticotropin-Releasing Hormone
CRF receptor type 1