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Paper for the Opened-Experiment of Medicinal Chemistry. ——Structure-Activity Study of β-Adrenergic Blockers and Laboratory Synthesis of Practolol. 68k JiDi Class Gracie L.C.
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——Structure-Activity Study of β-Adrenergic Blockers and Laboratory Synthesis of Practolol
68k JiDi Class
Abstract： The main content of the opened-experiment of medicinal chemistry is the design of a certain compound withβ-Adrenergic Blocking activity based on the study of its structure - activity relationship . Practolol, one compound in point, which is reported to have certain degree of β1-receptor selectivity and intrinsic sympathomimetic activity is chosen to be synthesized. This paper describes the decision making process in choosing object compound and the detailed laboratory procedure as well as discussion and analysis of problems arisen in the lab work.
Keywords :β-Adrenergic Blockers Structure-Activity Practolol Laboratory Synthesis
Figure.1:the similarity in the spatial relationship of the two typical structures
Figure2.the consistence in spatial configuration of the two structures
Aqueous solution is most stable at PH6(protected from light)
Raw Materials: 4-acetamidophenol (impure), epichlorohydrin, isopropylamine
Other Reagent: glacial acetate acid, alcohol absolute, activated charcoal
Apparatus for reflux: three-necked boiling flask(250ml,500ml), mechanical stirrer, iron rings, clamps, reflux condenser,
Apparatus for vacuum filtration: Buchner funnel, suction flask, water aspirator
Apparatus for distillation: distilling flask, condenser, distillation adapter, water aspirator
Others: beakers (several ), stirring rod, drying tube, infrared light, filter paper, boiling stones
Problem arose in the first step of the synthesis of Acebutolol :
（Ⅱ）(a kind of phenyl ester )
Descriptions in literature: The starting material were heated together under reflux until a solution formed. This solution was cooled and treated with water. The benzene layer was separated and the aqueous layer was again extracted with benzene. The extracts were dried and evaporated to dryness under reduced pressure to give (Ⅱ) as an off-white solid.
The actual phenomenon: After heating under reflux for 1 hour, the reaction mixture separated into two layers with the lower phase as kind of oil. The situation continued during the whole reflux process.