摘要
本文应用INDO波函数计算了三个芬太尼类化合物的分子静电势,酰胺氧原子周围均存在一个势阱很深的宽广的负电势区域,是最重要的负电中心,哌啶环4-位引入甲氧甲基后,增加了新的负电势区域,哌啶环1-位芳环周围具有宽广的正电势区域,哌啶氮原子和酰胺氮原子附近存在较小的负电势区域。基于计算出的静电势推测了三个化合物的镇痛作用的可能机理及药物结构与毒性的关系。
The molecular electrostatic potentials of fentanyl, 4-methoxymethyl-fentanyl and sufentanil have been calculated from INDO wave functions. For all the three compounds there is an extensive and deep negative potential well near the amide oxgyen, which is the most important negative electrostatic center. A new additional negative potential field, which is generated by the introduced 4-methoxymethyl group of piperidyl ring, may be the key factor for increasing the analgesic activity of 4-methoxymethyl-fentanyl and sufentanil. The positive potential field around the thiophene group is wider than that around the corresponding phenyl group. The negative potential field, generated by the piperidyl nitrogen and surrounded by pesitive potential regions, may be related to the analgesic activity, while the negative potential field near the amido nitrogen perhaps be related to the toxicity.
出处
《化学学报》
SCIE
CAS
CSCD
北大核心
1990年第7期660-665,共6页
Acta Chimica Sinica
