Investigation of phenolic bioisosterism in opiates: 3-sulfonamido analogues of naltrexone and oxymorphone

被引：19

作者：

McCurdy, CR ^{[1
]}

Jones, RM ^{[1
]}

Portoghese, PS ^{[1
]}

机构：

[1] Univ Minnesota, Coll Pharm, Dept Med Chem, Minneapolis, MN 55455 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 06期

关键词：

D O I：

10.1021/ol005561+

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The phenolic hydroxy group of opiate-derived ligands is of known importance for biological activity. On the basis of its putative role as a hydrogen-bonding donor in the interaction with opioid receptors, it was replaced with a sulfonamide group because of their similar pK(a) values. The first thebaine-derived 3-amino (8a, 8b) and subsequent sulfonamide analogues (10a, 10b) were synthesized from naltrexone (la) and oxymorphone (1b) in a linear nine-step synthesis. The sulfonamides were tested in vitro and found inactive.

引用

页码：819 / 821

页数：3

共 8 条

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[2]

Substituted (pyridylmethoxy)naphthalenes as potent and orally active 5-lipoxygenase inhibitors: Synthesis, biological profile, and pharmacokinetics of L-739,010 [J].