Deekonda2016

Deekonda2016
Identifiers
	IUPAC name N-[[1-[[(5S)-5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl]methyl]piperidin-2-yl]methyl]-N-phenylpropanamide;
CAS Number	1849034-34-9 ;
PubChem CID	127037397;
ChemSpider	58920549;
ChEMBL	ChEMBL3753293;
Chemical and physical data
Formula	C26H34N2O2
Molar mass	406.570 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=O)N(CC1CCCCN1CC2=CC3=C(C=C2)[C@H](CCC3)O)C4=CC=CC=C4;
	InChI InChI=1S/C26H34N2O2/c1-2-26(30)28(22-10-4-3-5-11-22)19-23-12-6-7-16-27(23)18-20-14-15-24-21(17-20)9-8-13-25(24)29/h3-5,10-11,14-15,17,23,25,29H,2,6-9,12-13,16,18-19H2,1H3/t23?,25-/m0/s1; Key:MSWKQEUSFJHFAI-YNMFNDETSA-N;

Deekonda2016 is a piperidine-based opioid analgesic compound, developed through modification of the fentanyl scaffold and with similar potency to fentanyl. It was designed as a mixed μ/δ opioid agonist but is much more selective for the μ-opioid receptor, with a binding affinity of 4 nM.^[1]^[2]^[3]^[4]

References

^ Deekonda S, Wugalter L, Kulkarni V, Rankin D, Largent-Milnes TM, Davis P, et al. (September 2015). "Discovery of 5-substituted tetrahydronaphthalen-2yl-methyl with N-phenyl-N-(piperidin-4-yl)propionamide derivatives as potent opioid receptor ligands". Bioorganic & Medicinal Chemistry. 23 (18): 6185–6194. doi:10.1016/j.bmc.2015.07.071. PMC 4642887. PMID 26299827.
^ Deekonda S, Rankin D, Davis P, Lai J, Vanderah TW, Porecca F, et al. (January 2016). "Design synthesis and structure-activity relationship of 5-substituted (tetrahydronaphthalen-2yl)methyl with N-phenyl-N-(piperidin-2-yl)propionamide derivatives as opioid ligands". Bioorganic & Medicinal Chemistry. 24 (2): 85–91. doi:10.1016/j.bmc.2015.11.030. PMC 4873254. PMID 26712115.
^ Lipiński PF, Kosson P, Matalińska J, Roszkowski P, Czarnocki Z, Jarończyk M, et al. (February 2019). "Fentanyl Family at the Mu-Opioid Receptor: Uniform Assessment of Binding and Computational Analysis". Molecules. 24 (4): 740. doi:10.3390/molecules24040740. PMC 6412969. PMID 30791394.
^ Wu Z, Hruby VJ (October 2019). "Toward a Universal μ-Agonist Template for Template-Based Alignment Modeling of Opioid Ligands". ACS Omega. 4 (17): 17457–17476. doi:10.1021/acsomega.9b02244. PMC 6812133. PMID 31656918.

[1] Deekonda S, Wugalter L, Kulkarni V, Rankin D, Largent-Milnes TM, Davis P, et al. (September 2015). "Discovery of 5-substituted tetrahydronaphthalen-2yl-methyl with N-phenyl-N-(piperidin-4-yl)propionamide derivatives as potent opioid receptor ligands". Bioorganic & Medicinal Chemistry. 23 (18): 6185–6194. doi:10.1016/j.bmc.2015.07.071. PMC 4642887. PMID 26299827.

[2] Deekonda S, Rankin D, Davis P, Lai J, Vanderah TW, Porecca F, et al. (January 2016). "Design synthesis and structure-activity relationship of 5-substituted (tetrahydronaphthalen-2yl)methyl with N-phenyl-N-(piperidin-2-yl)propionamide derivatives as opioid ligands". Bioorganic & Medicinal Chemistry. 24 (2): 85–91. doi:10.1016/j.bmc.2015.11.030. PMC 4873254. PMID 26712115.

[3] Lipiński PF, Kosson P, Matalińska J, Roszkowski P, Czarnocki Z, Jarończyk M, et al. (February 2019). "Fentanyl Family at the Mu-Opioid Receptor: Uniform Assessment of Binding and Computational Analysis". Molecules. 24 (4): 740. doi:10.3390/molecules24040740. PMC 6412969. PMID 30791394.

[4] Wu Z, Hruby VJ (October 2019). "Toward a Universal μ-Agonist Template for Template-Based Alignment Modeling of Opioid Ligands". ACS Omega. 4 (17): 17457–17476. doi:10.1021/acsomega.9b02244. PMC 6812133. PMID 31656918.

[1]

[2]

[3]

[4]

See also

References