14-烷氧基吗啡喃的合成与生物学评价。3. 对环丙胺相关化合物的深入研究。
Synthesis and biological evaluation of 14-alkoxymorphinans. 3. Extensive study on cyprodime-related compounds.
作者信息
Schmidhammer H, Smith C F, Erlach D, Koch M, Krassnig R, Schwetz W, Wechner C
机构信息
Institute of Organic and Pharmaceutical Chemistry, University of Innsbruck, Austria.
出版信息
J Med Chem. 1990 Apr;33(4):1200-6. doi: 10.1021/jm00166a018.
A series of cyprodime-related compounds (2, 4-12, and 26) has been synthesized and evaluated for opioid agonist and antagonist activity with the mouse vas deferens and guinea pig ileum preparations. None of the changes to cyprodime, including the introduction of a 3-OMe group, increasing and decreasing the size of or completely removing the substituent in position 4, replacing the N-cyclopropylmethyl group with an N-allyl group, or replacing the 14-OMe with an 14-OEt substituent, resulted in an improved mu antagonist profile and most were detrimental either in terms of mu selectivity and potency or increased agonist activity. Increasing the length of the substituent in position 4 resulted in a compound (6a) with a very similar profile to that of cyprodime.
已合成了一系列与环丙吗啉相关的化合物（2、4 - 12和26），并使用小鼠输精管和豚鼠回肠标本对其阿片样物质激动剂和拮抗剂活性进行了评估。对环丙吗啉所做的任何改变，包括引入3 - OMe基团、增大或减小4位取代基的大小或完全去除该取代基、用N - 烯丙基取代N - 环丙基甲基基团或用14 - OEt取代14 - OMe，均未产生改善的μ拮抗剂特征，并且大多数在μ选择性和效力方面或增加的激动剂活性方面是有害的。增加4位取代基的长度得到了一种化合物（6a），其特征与环丙吗啉非常相似。
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