HOMEPRODUCTSCOMPANYCONTACTFAQResearchDictionaryPharmaSign Up FREE or Login

6-Methyl-6-azabicyclo[3.2.1]octan-3 alpha-ol 2,2-diphenylpropionate (azaprophen), a highly potent antimuscarinic agent.

Abstract
The synthesis and antimuscarinic properties of 6-methyl-6-azabicyclo[3.2.1]octan-3 alpha-ol 2,2-diphenylpropionate (1, azaprophen) are described. Azaprophen is 50 times more potent than atropine as an antimuscarinic agent as measured by the inhibition of acetylcholine-induced contraction of guinea pig ileum and is more than 1000 times better than atropine in its ability to block alpha-amylase release from pancreatic acini cells induced by carbachol. In addition, azaprophen is 27 times more potent than atropine as an inhibitor of binding of [N-methyl-3H]scopolamine to muscarinic receptors, with human IMR-30 neuroblastoma cells. The potencies of azaprophen and atropine in altering operant behavior were similar. The structural features of 1 are compared to the standard anticholinergic drugs atropine and quinuclidinyl benzilate by using energy calculations and molecular modelling studies. A modification of the pharmacophore model hypothesis for cholinergic agents is suggested.
AuthorsF I Carroll, P Abraham, K Parham, R C Griffith, A Ahmad, M M Richard, F N Padilla, J M Witkin, P K Chiang
JournalJournal of medicinal chemistry (J Med Chem) Vol. 30 Issue 5 Pg. 805-9 (May 1987) ISSN: 0022-2623 [Print] United States
PMID3494849 (Publication Type: Comparative Study, Journal Article)
Chemical References
  • Phenylpropionates
  • Receptors, Muscarinic
  • Tropanes
  • azaprophen
  • Carbachol
  • Scopolamine
  • alpha-Amylases
  • Acetylcholine
Topics
  • Acetylcholine (pharmacology)
  • Animals
  • Behavior, Animal (drug effects)
  • Carbachol (pharmacology)
  • Cell Line
  • Chemical Phenomena
  • Chemistry
  • Guinea Pigs
  • Humans
  • Male
  • Molecular Conformation
  • Muscle Contraction (drug effects)
  • Neuroblastoma (metabolism)
  • Pancreas (drug effects, enzymology)
  • Phenylpropionates (chemical synthesis, pharmacology)
  • Rats
  • Rats, Inbred Strains
  • Receptors, Muscarinic (drug effects)
  • Scopolamine (metabolism)
  • Tropanes (chemical synthesis, pharmacology)
  • alpha-Amylases (metabolism)

Join CureHunter, for free Research Interface BASIC access!

Take advantage of free CureHunter research engine access to explore the best drug and treatment options for any disease. Find out why thousands of doctors, pharma researchers and patient activists around the world use CureHunter every day.
Realize the full power of the drug-disease research graph!


Choose Username:
Email:
Password:
Verify Password:
Enter Code Shown: