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Citation: Chen Chang-Ying, Li Yu-Lin, Lian Hong-Shou, Chen Ji-Sheng. Studies on Action of 4-Substituent in Fentanyl Derivatives[J]. Acta Physico-Chimica Sinica, ;1990, 6(01): 17-22. doi: 10.3866/PKU.WHXB19900104 shu

Studies on Action of 4-Substituent in Fentanyl Derivatives

1.
Institute of Pharmaceutical Chemistry,PLA,Beijing

Received Date: 28 March 1988
Available Online: 15 February 1990

The electronic structures and conformations of non-polar-substituted 4-n-propyl-fentanyl and polar substituted 4-methoxymethyl-fentanyl and 4-methoxycarbonyl-fentanyl were investigated by the method of quantum mechanics. The results showed that the cause of effect of 4-substituent on biological activity not that change of conformations but that electronic factors. The 4-non-polar-substituents have not con-tribution upon increase of activity. The 4-polar-substituents form new additional negative electronic region, which may be the main assistant site interacting with receptor, the additional negative electrostatic potential region may interact with receptor at a new site or the site in common with amide oxygen. It is no doubt that the additional negative electrostatic potential field generated by the 4-polar-substituent dramatically increases the analgesic activity of the fentanyl derivatives.
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