期刊
ORGANIC LETTERS
卷 2, 期 6, 页码 819-821出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol005561+
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资金
- NIDA NIH HHS [DA01533, T32DA07234] Funding Source: Medline
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.
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