Synthesis and SAR of analogs of the M1 allosteric agonist TBPB. Part II: Amides, sulfonamides and ureas--the effect of capping the distal basic piperidine nitrogen.

Miller NR, Daniels RN, Bridges TM, Brady AE, Conn PJ, Lindsley CW
Bioorg Med Chem Lett. 2008 18 (20): 5443-7

PMID: 18829311 · PMCID: PMC3177607 · DOI:10.1016/j.bmcl.2008.09.032

This letter describes the further synthesis and SAR, developed through an iterative analog library approach, of analogs of the highly selective M1 allosteric agonist TBPB by deletion of the distal basic piperidine nitrogen by the formation of amides, sulfonamides and ureas. Despite the large change in basicity and topology, M1 selectivity was maintained.

MeSH Terms (15)

Allosteric Regulation Allosteric Site Amides Benzimidazoles Chemistry, Pharmaceutical Dose-Response Relationship, Drug Drug Design Humans Models, Chemical Nitrogen Piperidines Receptor, Muscarinic M1 Structure-Activity Relationship Sulfonamides Urea

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