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1 - benzyl-4 - methoxycarbonyl fentanyl Synthesis and comparative molecular field analysis

Author: WuQiangSan
Tutor: HuWenXiang
School: Capital Normal University
Course: Physical and chemical
Keywords: Powerful analgesics Fentanyl 4 - methoxy - carbonyl fentanyl Vulcanization Orthogonal experiment
CLC: TQ463
Type: Master's thesis
Year: 2008
Downloads: 61
Quote: 0
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Abstract


As early as in the early 1960s , the Belgians Janssen et al first reported a new potent analgesic fentanyl , after the study of this class of drugs has caused a great deal of concern . Fentanyl is a the famous efficient narcotic analgesics , pain intensity , fast-acting and short duration . The four substituted fentanyl derivatives , such as 4 - methoxycarbonyl fentanyl and 4 - methoxymethyl fentanyl is one of analgesic activity of one of the strongest type , wherein the card fentanyl analgesia activity of morphine 10,031 times . From such derivatives developed Sufentanil and Alfentanil has been applied to clinical stability analgesia and anesthesia , and little effect on the cardiovascular system , widely used in heart surgery . Firstly, the use of computer-aided drug design means fentanyl class of compounds , the of three quantitative relationship study (3D-QSAR) structure-activity relationships , research methods using comparative molecular field analysis (CoMFA) method ; using GALAHAD completed of anticonvulsant drugs pharmacophore search and three quantitative structure-activity relationship studies based on search pharmacophore ; 1 - benzyl 4 - piperidone as raw materials under the guidance of reference after the addition, hydrolysis , hydrolysis, esterification , acylation again synthesized a series of compounds of fentanyl ; during the experiment , the experimental conditions were optimized , so that the reaction yield increased threefold ; also used by microwave catalyzed orthogonal experiment method to improve the synthesis of 1 - benzyl-4 - methoxycarbonyl - anilino- piperidine reaction steps , the conventional reaction yield from 55.6 % to 79% , the reaction time from 72 hours shortened to 1.5 hours ; addition , after groping several experimental conditions , P 2 S 5 card fentanyl sulfide .

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Production of organic compounds in drug
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