Chemistry:A-85380

From HandWiki

A-85380 is a chemical compound that acts as a potent and selective agonist of nicotinic acetylcholine receptors (nAChRs), particularly the α4β2 subtype. It has been primarily used in scientific research to explore the structure and function of neuronal nAChRs and their role in neurodegenerative diseases, addiction, and cognition.[1][2]

Synthesis

A-85380 synthesis:[3]

The Mitsunobu reaction between (S)-1-Boc-2-azetidinemethanol [161511-85-9] (1) and 3-hydroxypyridine [109-00-2] (2) gives Tert-butyl (2S)-2-(pyridin-3-yloxymethyl)azetidine-1-carboxylate, PC10801571 (3). Acid deprotection of the urethane completed the synthesis of A-85380 (4).

See also

References

  1. "A-85380 [3-(2(S)-azetidinylmethoxy) pyridine]: in vitro pharmacological properties of a novel, high affinity alpha 4 beta 2 nicotinic acetylcholine receptor ligand". Neuropharmacology 35 (6): 725–734. June 1996. doi:10.1016/0028-3908(96)84644-2. PMID 8887981. 
  2. "A-85380: a pharmacological probe for the preclinical and clinical investigation of the alphabeta neuronal nicotinic acetylcholine receptor". CNS Drug Reviews 12 (2): 100–112. June 2006. doi:10.1111/j.1527-3458.2006.00100.x. PMID 16958984. 
  3. "Novel 3-Pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors". Journal of Medicinal Chemistry 39 (4): 817–825. February 1996. doi:10.1021/jm9506884. PMID 8632405.