Bioisosterism: Interchange of 4-OH to 4-NH2 in vanillin or homovanillin ring of capsaicinoids
- 1 April 1999
- journal article
- research article
- Published by Springer Nature in Archives of Pharmacal Research
- Vol. 22 (2) , 184-188
- https://doi.org/10.1007/bf02976544
Abstract
A series of 4-amino Capsaicin analogs15, 17 and19 were prepared to investigate the bioisosteric effect of 4-amino group, and all these compounds exhibited moderate or weak potency from their analgesic test. From our previous results and others, 4-hydroxyl group, as well as 3-methoxy substituent could be crucial for high analgesic activity. This biological result also shows that the activity is sensitive to alkyl chain length in hydrophobic region and the phenylacetic amides19 are more active than the corresponding urea derivatives17.Keywords
This publication has 7 references indexed in Scilit:
- Homovanillic amide derivatives as capsaicin analogs and their analgesic activityArchives of Pharmacal Research, 1997
- Synthesis of homovanillic amide derivatives and their analgesic activityArchives of Pharmacal Research, 1996
- Analogues of Capsaicin with Agonist Activity as Novel Analgesic Agents: Structure−Activity Studies. 4. Potent, Orally Active AnalgesicsJournal of Medicinal Chemistry, 1996
- Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 1. The aromatic "A-region"Journal of Medicinal Chemistry, 1993
- The neuropharmacology of capsaicin: review of some recent observations.Pharmacological Reviews, 1986
- Propane-1,3-dithiol: A selective reagent for the efficient reduction of alkyl and aryl azides to aminesTetrahedron Letters, 1978