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Tetrahydropyridinylindole

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Tetrahydropyridinylindoles (THPIs) are a group of chemical compounds related to the tryptamines.[1] They can be subdivided into 3-(1,2,5,6-tetrahydropyridin-4-yl)indoles (4-THPIs or simply THPIs) and 3-(1,2,5,6-tetrahydropyridin-3-yl)indoles (3-THPIs).[1][2] 3-THPIs are cyclized tryptamines and include RS134-49, RU-28253, and NEtPhOH-THPI, whereas 4-THPIs are not technically tryptamines but are closely related, with examples including THPI, RU-24969 (5-MeO-THPI), EMD-386088, MTHPI, tepirindole (RU-27592), Lu 35-138, and LY-367265. Tetrahydropyridinylindoles of both of the preceding groups are known to act as serotonin receptor modulators.[3][4][5][6][7]

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References

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  1. 1 2 Cornfield, L. J. (1990). Characterization of structure-activity relationships for serotonin receptors coupled to adenylate cyclase. The University of Arizona. http://hdl.handle.net/10150/185101 "The work discussed in this chapter extends the previous study by examining relationships between structure and intrinsic activity at 5-HT1A receptors in a larger series of tetrahydropyridinyl analogs, specifically 3-(1,2,5,6-tetrahydropyridin-4-yl)indoles (4-THPI) and 3-(1,2,5,6-tetrahydropyridin-3-yl)indoles (3-THPI). [...]"
  2. ↑ Dahlgren, T.; Dean, R.L.; Gharat, L.A.; Johansson, A.M.; Lambert, G.; Li, H.B.; Nelson, D.L.; Yang, Y.; Martin, A.R. (1995). "Synthesis and serotonin receptor binding properties of 5-substituted 3-(1′,2′,5′,6′-tetrahydropyridin-3′-yl) indoles". Bioorganic & Medicinal Chemistry Letters. 5 (24): 2963–2968. doi:10.1016/0960-894X(95)00534-8. Retrieved 5 October 2026.
  3. ↑ Taylor EW, Nikam S, Weck B, Martin A, Nelson D (October 1987). "Relative selectivity of some conformationally constrained tryptamine analogs at 5-HT1, 5-HT1A and 5-HT2 recognition sites". Life Sci. 41 (16): 1961–1969. doi:10.1016/0024-3205(87)90749-1. PMID 3657392.
  4. ↑ Agarwal A, Pearson PP, Taylor EW, Li HB, Dahlgren T, Herslöf M, Yang Y, Lambert G, Nelson DL, Regan JW (December 1993). "Three-dimensional quantitative structure-activity relationships of 5-HT receptor binding data for tetrahydropyridinylindole derivatives: a comparison of the Hansch and CoMFA methods". J Med Chem. 36 (25): 4006–14. doi:10.1021/jm00077a003. PMID 8258822.
  5. ↑ Bojarski AJ (2006). "Pharmacophore models for metabotropic 5-HT receptor ligands". Curr Top Med Chem. 6 (18): 2005–26. doi:10.2174/156802606778522186. PMID 17017971.
  6. ↑ Kitson SL (2007). "5-hydroxytryptamine (5-HT) receptor ligands". Curr Pharm Des. 13 (25): 2621–2637. doi:10.2174/138161207781663000. PMID 17897004.
  7. ↑ Wróbel MZ, Chodkowski A, Siwek A, Satała G, Bojarski AJ, Dawidowski M (October 2024). "Design and Synthesis of Potential Multi-Target Antidepressants: Exploration of 1-(4-(7-Azaindole)-3,6-dihydropyridin-1-yl)alkyl-3-(1H-indol-3-yl)pyrrolidine-2,5-dione Derivatives with Affinity for the Serotonin Transporter". Int J Mol Sci. 25 (20) 11276. doi:10.3390/ijms252011276. PMC 11508649. PMID 39457057.


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