Rogers, Gary A.; Parsons, Stanley M.; Anderson, D. C.; Nilsson, Lena M.; Bahr, Ben A.; Kornreich, Wayne D.; Kaufman, Rose; Jacobs, Robert S.; Kirtman, Bernard published the artcile< Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogs of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol)>, Electric Literature of 112-63-0, the main research area is vesamicol analog preparation acetylcholine blocking; phenylpiperidinocychlohexanol analog preparation; piperidinocyclohexanol; structure activity vesamicol analog acetylcholine blocking.
Eighty-four analogs, e.g., I [R = (un)substituted Ph, cyclohexyl, PhCH2, Ph(CH2)3] and derivatives of the acetylcholine storage-blocking drug trans-2-4(4-phenylpiperidino)cyclohexanol (vesamicol) were synthesized, and their potencies were evaluated with the acetylcholine active-transport assay utilizing purified synaptic vesicles from Torpedo elec. organ. The parent drug exhibits enantioselectivity, with (-)-vesamicol being 25-fold more potent than (+)-vesamicol. The mol. structure and absolute configuration of (+)-vesamicol were determined by x-ray crystallog. The absolute configuration of (-)-vesamicol is (1R,2R). Structure-activity evidence indicates that (-)-vesamicol does not act as an acetylcholine analog. Alterations to all three rings can have large effects on potency. Unexpectedly, analogs locking the alc. and ammonium groups trans-diequatorial or trans-diaxial both exhibit good potency. A potent benzovesamicol family was discovered that is suitable for facile elaboration of the sort useful in affinity labeling and affinity chromatog. applications. A good correlation was found between potencies as assessed by the acetylcholine transport assay and LD50 values in mouse.
Journal of Medicinal Chemistry published new progress about Cholinergic receptors Role: RCT (Reactant), RACT (Reactant or Reagent). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Electric Literature of 112-63-0.
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