BU09059

BU09059
Identifiers
	IUPAC name ethyl 2-{[(3R)-7-hydroxy-1,2,3,4-tetrahydroisoquinolin-3-yl]formamido}-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoate;
CAS Number	1541206-05-6;
PubChem CID	134817175;
Chemical and physical data
Formula	C28H37N3O5
Molar mass	495.620 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC(=O)C(CN1CC[C@](C)([C@@H](C)C1)c2cccc(O)c2)NC(=O)[C@H]3Cc4ccc(O)cc4CN3;
	InChI InChI=1S/C28H37N3O5/c1-4-36-27(35)25(30-26(34)24-13-19-8-9-23(33)12-20(19)15-29-24)17-31-11-10-28(3,18(2)16-31)21-6-5-7-22(32)14-21/h5-9,12,14,18,24-25,29,32-33H,4,10-11,13,15-17H2,1-3H3,(H,30,34)/t18-,24+,25?,28+/m0/s1; Key:RKGRJMYCISUSNK-XTNINKNLSA-N;

BU09059 is a potent, selective, short-acting (non-"inactivating") antagonist of the κ-opioid receptor (KOR).^[1]^[2] It was derived from the irreversible (long-acting) KOR antagonist JDTic in search of an antagonist with a reversible profile of inactivation of the KOR that could be used with less concern to treat psychiatric disorders.^[1]^[2] In addition to its reversibility, BU09059 is much more selective for the KOR than JDTic, showing 15-fold and 616-fold preference for the KOR over the μ- and δ-opioid receptors (K_i = 1.72 nM, 26.5 nM, and 1060 nM, respectively).^[1]

References

^ ^a ^b ^c Casal-Dominguez JJ, Furkert D, Ostovar M, Teintang L, Clark MJ, Traynor JR, et al. (March 2014). "Characterization of BU09059: a novel potent selective κ-receptor antagonist". ACS Chemical Neuroscience. 5 (3): 177–84. doi:10.1021/cn4001507. PMC 3963132. PMID 24410326.
^ ^a ^b Urbano M, Guerrero M, Rosen H, Roberts E (May 2014). "Antagonists of the kappa opioid receptor". Bioorganic & Medicinal Chemistry Letters. 24 (9): 2021–32. doi:10.1016/j.bmcl.2014.03.040. PMID 24690494.

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[Casal-DominguezFurkert2014-1] Casal-Dominguez JJ, Furkert D, Ostovar M, Teintang L, Clark MJ, Traynor JR, et al. (March 2014). "Characterization of BU09059: a novel potent selective κ-receptor antagonist". ACS Chemical Neuroscience. 5 (3): 177–84. doi:10.1021/cn4001507. PMC 3963132. PMID 24410326.

[UrbanoGuerrero2014-2] Urbano M, Guerrero M, Rosen H, Roberts E (May 2014). "Antagonists of the kappa opioid receptor". Bioorganic & Medicinal Chemistry Letters. 24 (9): 2021–32. doi:10.1016/j.bmcl.2014.03.040. PMID 24690494.

[1]

[2]

Identifiers

IUPAC name ethyl 2-{[(3R)-7-hydroxy-1,2,3,4-tetrahydroisoquinolin-3-yl]formamido}-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoate
CAS Number	1541206-05-6
PubChem CID	134817175
Chemical and physical data
Formula	C₂₈H₃₇N₃O₅
Molar mass	495.620 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCOC(=O)C(CN1CC[C@](C)([C@@H](C)C1)c2cccc(O)c2)NC(=O)[C@H]3Cc4ccc(O)cc4CN3
InChI InChI=1S/C28H37N3O5/c1-4-36-27(35)25(30-26(34)24-13-19-8-9-23(33)12-20(19)15-29-24)17-31-11-10-28(3,18(2)16-31)21-6-5-7-22(32)14-21/h5-9,12,14,18,24-25,29,32-33H,4,10-11,13,15-17H2,1-3H3,(H,30,34)/t18-,24+,25?,28+/m0/s1 Key:RKGRJMYCISUSNK-XTNINKNLSA-N

BU09059

See also

References