New aporphinoid 5-HT2A and α1A antagonists via structural manipulations of nantenine.
Sandeep Chaudhary, Shashikanth Ponnala, Onica Legendre, Junior A Gonzales, Hernan Navarro, Wayne W Harding
Bioorganic & Medicinal Chemistry August 18, 2011 DOI: 10.1016/j.bmc.2011.08.019 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | Serotonin |
| Keywords | Aporphines Receptors, adrenergic, alpha-1 Receptor, serotonin, 5-ht2a Structure-activity relationship |
| Key points | Alkyl substitution at C1 of nantenine yields selective 5-HT(2A) antagonists, while N6 alkyl substitution yields selective alpha(1A) antagonists. C2 alkyloxy analogs are generally alpha(1A)-selective, and the C3 bromo analog 15 is reported as one of the most potent aporphinoid 5-HT(2A) antagonists known. |
Abstract
A series of C1, C2, C3 and N6 analogs of nantenine (2) was synthesized and evaluated in 5-HT(2A) and α(1A) receptor functional assays. Alkyl substitution of the C1 and N6 methyl groups of nantenine provided selective 5-HT(2A) and α(1A) antagonists, respectively. The C2 alkyloxy analogs studied were generally selective for α(1A) versus 5-HT(2A). The C3 bromo analog 15 is one of the most potent aporphinoid 5-HT(2A) antagonists known presently.
Citations in the library
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