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A series of cis- and trans-fused hexahydroindeno[2,1-c]pyridines have been prepared and evaluated for affinity and selectivity at the 5-HT(1A) subtype of the serotonin receptor. Using molecular modeling studies we predicted that the 5-methoxy-trans-fused members of this class would exhibit affinity for this site. In agreement with these predictions, trans-5-methoxy-N-propyl- 2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-c]pyridine (6a) demonstrated moderate affinity and high selectivity for the 5-HT(1A) binding site, whereas the cis- fused isomer 5a demonstrated virtually no affinity at this site. Additional trans-fused analogs from this series, where the nitrogen was substituted with a variety of alkylene imide containing appendages, demonstrated high (0.60- 51 nM) affinity and excellent selectivity for the 5-HT(1A) site. Certain of these analogs, independent of ring-fusion stereochemistry, also demonstrated high affinity for the 5-HT2 binding site.
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Reference：
Piperidine – Wikipedia,
Piperidine | C5H19846N – PubChem