CBM 301940

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CBM 301940
Category Enzyme inhibitors
Catalog number BBF-04521
CAS 902146-11-6
Molecular Weight 422.32
Molecular Formula C15H20F6N2O5
Purity ≥98%

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Description

Malonyl-CoA decarboxylase (MCD) is found from bacteria to humans, which has important roles in regulating fatty acid metabolism and food intake. CBM 301940 is a potent malonyl-CoA decarboxylase (MCD) inhibitor with IC50 of 23 nM. It suppresses malonyl-CoA degradation and fatty acid oxidation in isolated rat hearts, leading to secondary increase in glucose oxidation.

Specification

Synonyms (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester; CBM301940; CBM-301940
Storage Store at -20°C
IUPAC Name tert-butyl 3-[[5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4,5-dihydro-1,2-oxazole-3-carbonyl]amino]butanoate
Canonical SMILES CC(NC(C1=NOC(C(C(F)(F)F)(O)C(F)(F)F)C1)=O)CC(OC(C)(C)(C)=O
InChI InChI=1S/C15H20F6N2O5/c1-7(5-10(24)27-12(2,3)4)22-11(25)8-6-9(28-23-8)13(26,14(16,17)18)15(19,20)21/h7,9,26H,5-6H2,1-4H3,(H,22,25)
InChI Key SBPVPWWNQIKSKL-UHFFFAOYSA-N

Properties

Appearance Off-white Solid
Density 1.4±0.1 g/cm3
Solubility Soluble in DMSO (100 mM), Ethanol (100 mM)

Reference Reading

1. Discovery of potent and orally available malonyl-CoA decarboxylase inhibitors as cardioprotective agents
Rick Barr, Masahiro Nishimoto, Thomas Arrhenius, Yujin Huang, Eoin O'leary, Larry Liu, Richard Penuliar, Alex M Nadzan, Miguel Barbosa, Jason R B Dyck, Gary D Lopaschuk, Guang Yang, Jie-Fei Cheng J Med Chem . 2006 Jul 13;49(14):4055-8. doi: 10.1021/jm0605029.
Discovery of 5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4,5-dihydroisoxazole-3-carboxamides as a new class of malonyl-coenzyme A decarboxylase (MCD) inhibitors is described. tert-Butyl 3-(5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4,5-dihydroisoxazole-3-carboxamido)butanoate (5, CBM-301940) exhibited excellent potency and in vivo PK/ADME properties. It is the most powerful stimulant of glucose oxidation reported to date in isolated working rat hearts. Compound 5 improved the cardiac efficiency and function in a rat heart global ischemia/reperfusion model, suggesting MCD inhibitors may be useful for the treatment of ischemic heart diseases.

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