SCH-202,596

SCH-202,596
Clinical data
ATC code	none;
Identifiers
	IUPAC name methyl (2S)-5,7-dichloro-5'-methoxy-6-methyl-3,3'-dioxo-4-([(1R,4R,5R,6S)-4,5,6-trihydroxy-2-methoxycarbonyl-1-cyclohex-2-enyl]oxy)spiro[1-benzofuran-2,6'-cyclohexa-1,4-diene]-1'-carboxylate;
CAS Number	196615-89-1;
PubChem CID	11758032;
IUPHAR/BPS	6128;
ChemSpider	9932733;
CompTox Dashboard (EPA)	DTXSID401032022 ;
Chemical and physical data
Formula	C25H22Cl2O12
Molar mass	585.34 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OC)\C4=C\[C@@H](O)[C@@H](O)[C@H](O)[C@@H]4Oc2c(Cl)c(c(Cl)c1O[C@@]3(C(=O)c12)C(/C(=O)OC)=C\C(=O)\C=C3\OC)C;
	InChI InChI=1S/C25H22Cl2O12/c1-8-15(26)20(38-19-10(23(33)36-3)7-12(29)17(30)18(19)31)14-21(16(8)27)39-25(22(14)32)11(24(34)37-4)5-9(28)6-13(25)35-2/h5-7,12,17-19,29-31H,1-4H3/t12-,17-,18+,19-,25+/m1/s1; Key:LNGFWDFUPRZMJI-VEHFIHCQSA-N;

SCH-202,596 is a natural product which is a metabolite derived from an Aspergillus fungus. It acts as a selective non-peptide antagonist for the receptor GAL-1, which is usually activated by the neuropeptide galanin. SCH-202,596 is used for scientific research into this still little characterised receptor subtype.^[1]^[2]

References

^ Min C, Mierzwa R, Truumees I, King A, Sapidou E, Barrabee E, et al. (September 1997). "A new fungal metabolite, Sch 202596, with inhibitory activity in the galanin receptor GALR1 assay". Tetrahedron Letters. 38 (35): 6111–4. doi:10.1016/S0040-4039(97)01385-3.
^ Katoh T, Ohmori O, Iwasaki K, Inoue M (February 2002). "Synthetic studies on Sch 202596, an antagonist of the galanin receptor subtype GalR1: an efficient synthesis of (±)-geodin, the spirocoumaranone part of Sch 202596". Tetrahedron. 58 (7): 1289–99. doi:10.1016/S0040-4020(01)01250-9.

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[1] Min C, Mierzwa R, Truumees I, King A, Sapidou E, Barrabee E, et al. (September 1997). "A new fungal metabolite, Sch 202596, with inhibitory activity in the galanin receptor GALR1 assay". Tetrahedron Letters. 38 (35): 6111–4. doi:10.1016/S0040-4039(97)01385-3.

[2] Katoh T, Ohmori O, Iwasaki K, Inoue M (February 2002). "Synthetic studies on Sch 202596, an antagonist of the galanin receptor subtype GalR1: an efficient synthesis of (±)-geodin, the spirocoumaranone part of Sch 202596". Tetrahedron. 58 (7): 1289–99. doi:10.1016/S0040-4020(01)01250-9.

[1]

[2]

Clinical data

ATC code	none
Identifiers
IUPAC name methyl (2S)-5,7-dichloro-5'-methoxy-6-methyl-3,3'-dioxo-4-([(1R,4R,5R,6S)-4,5,6-trihydroxy-2-methoxycarbonyl-1-cyclohex-2-enyl]oxy)spiro[1-benzofuran-2,6'-cyclohexa-1,4-diene]-1'-carboxylate
CAS Number	196615-89-1
PubChem CID	11758032
IUPHAR/BPS	6128
ChemSpider	9932733
CompTox Dashboard (EPA)	DTXSID401032022
Chemical and physical data
Formula	C₂₅H₂₂Cl₂O₁₂
Molar mass	585.34 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(OC)\C4=C\[C@@H](O)[C@@H](O)[C@H](O)[C@@H]4Oc2c(Cl)c(c(Cl)c1O[C@@]3(C(=O)c12)C(/C(=O)OC)=C\C(=O)\C=C3\OC)C
InChI InChI=1S/C25H22Cl2O12/c1-8-15(26)20(38-19-10(23(33)36-3)7-12(29)17(30)18(19)31)14-21(16(8)27)39-25(22(14)32)11(24(34)37-4)5-9(28)6-13(25)35-2/h5-7,12,17-19,29-31H,1-4H3/t12-,17-,18+,19-,25+/m1/s1 Key:LNGFWDFUPRZMJI-VEHFIHCQSA-N