Allosteric Activation of α7 Nicotinic Acetylcholine Receptors by Novel 2-Arylamino-thiazole-5-carboxylic Acid Amide Derivatives for the Improvement of Cognitive Deficits in Mice

J Med Chem. 2024 Apr 25;67(8):6344-6364. doi: 10.1021/acs.jmedchem.3c02323. Epub 2024 Feb 23.

Abstract

Enhancing α7 nAChR function serves as a therapeutic strategy for cognitive disorders. Here, we report the synthesis and evaluation of 2-arylamino-thiazole-5-carboxylic acid amide derivatives 6-9 that as positive allosteric modulators (PAMs) activate human α7 nAChR current expressed in Xenopus ooctyes. Among the 4-amino derivatives, a representative atypical type I PAM 6p exhibits potent activation of α7 current with an EC50 of 1.3 μM and the maximum activation effect on the current over 48-fold in the presence of acetylcholine (100 μM). The structure-activity relationship (SAR) analysis reveals that the 4-amino group is crucial for the allosteric activation of α7 currents by compound 6p as the substitution of 4-methyl group results in its conversion to compound 7b (EC50 = 2.1 μM; max effect: 58-fold) characterized as a typical type I PAM. Furthermore, both 6p and 7b are able to rescue auditory gating deficits in mouse schizophrenia-like model of acoustic startle prepulse inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allosteric Regulation / drug effects
  • Amides / chemical synthesis
  • Amides / chemistry
  • Amides / pharmacology
  • Animals
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology
  • Cognitive Dysfunction / drug therapy
  • Cognitive Dysfunction / metabolism
  • Humans
  • Male
  • Mice
  • Structure-Activity Relationship
  • Thiazoles* / chemical synthesis
  • Thiazoles* / chemistry
  • Thiazoles* / pharmacology
  • Thiazoles* / therapeutic use
  • Xenopus laevis
  • alpha7 Nicotinic Acetylcholine Receptor* / agonists
  • alpha7 Nicotinic Acetylcholine Receptor* / metabolism

Substances

  • alpha7 Nicotinic Acetylcholine Receptor
  • Thiazoles
  • Carboxylic Acids
  • Amides