Molecular requirements of the active site of cholinergic receptors XV: Synthesis and biological activity of 2,3-dehydrodeoxamuscarone and 2,3-dehydrodeoxamuscarines.
To elucidate the molecular requirements of the active sites of cholinergic receptors, 3-methyl-4-oxo-1-(N,N-dimethylaminomethyl)cyclopent-2-ene methiodide (2,3-dehydrodeoxamuscarone) and cis- and trans-3-methyl-4-hydroxy-1-(N,N-dimethylaminomethyl)cyclopent-2-ene methiodides (cis- and trans-dehydrodeoxamuscarines) were synthesized and tested. The results, compared with those of the corresponding oxygenated compounds, seem to indicate the 2,3-dehydrodeoxamuscarines and muscarine bind at the same site while 2,3-dehydrodeoxamuscarone interacts with the site normally occupied by muscarone. Furthermore, the previously suggested hypothesis that the unpolar site might somehow incorporate that of muscarone was considered.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000494:pharmacology; D006168:Guinea Pigs; D066298:In Vitro Techniques; D010277:Parasympathomimetics / Q000138:chemical synthesis*; D011898:Ranidae; D011950:Receptors, Cholinergic / Q000187:drug effects*; D013329:Structure-Activity Relationship
D003517:Cyclopentanes; D010277:Parasympathomimetics; D011950:Receptors, Cholinergic; C030550:2,3-dehydrodeoxamuscarine; C030551:2,3-dehydrodeoxamuscarone