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371942-69-7

371942-69-7 Structure

371942-69-7 Structure
IdentificationBack Directory
[Name]

6-Amino-N-[3-[4-(4-morpholinyl)pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl]phenyl]-3-pyridinecarboxamide
[CAS]

371942-69-7
[Synonyms]

CS-335
YM 201636
YM201636 HCl
YM201636, >=98%
YM201636/YM-201636
6-amino-N-(3-(4-morpholinopyrido[3,,2,:4,5]furo[3,2-d]pyrimidin-2-yl)phenyl)nicotinamide
3-Pyridinecarboxamide, 6-amino-N-[3-[4-(4-morpholinyl)pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-
6-amino-N-(3-(4-morpholinopyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl)phenyl)nicotinamide hydrochloride
6-Amino-N-[3-[4-(4-morpholinyl)pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl]phenyl]-3-pyridinecarboxamide
3-Pyridinecarboxamide, 6-amino-N-[3-[4-(4-morpholinyl)pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl]phenyl]-
6-Amino-N-[3-[4-(4-morpholinyl)pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl]phenyl]-3-pyridinecarboxamide USP/EP/BP
YM 201636 6-Amino-N-[3-[4-(4-morpholinyl)pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl]phenyl]-3-pyridinecarboxamide
6-Amino-N-[3-[4-(4-morpholinyl)pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl]phenyl]-3-pyridinecarboxamide YM201636
[Molecular Formula]

C25H21N7O3
[MDL Number]

MFCD16038303
[MOL File]

371942-69-7.mol
[Molecular Weight]

467.48
Chemical PropertiesBack Directory
[Melting point ]

>226°C (dec.)
[density ]

1.446
[storage temp. ]

-20°C Freezer
[solubility ]

DMSO (Slightly), Methanol (Very Slightly)
[form ]

Solid
[color ]

Pale Beige to Light Beige
[InChIKey]

YBPIBGNBHHGLEB-UHFFFAOYSA-N
[SMILES]

N6(CCOCC6)c1nc(nc4c1[o]c5ncccc54)c2cc(ccc2)NC(=O)c3cnc(cc3)N
[CAS DataBase Reference]

371942-69-7
Safety DataBack Directory
[WGK Germany ]

WGK 1
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

YM 201636 is a phosphatidylinositol phosphate kinase PIP5KIII (PIKfyve) inhibitor and significantly reduces the survival of primary mouse hippocampal neurons in culture. YM-201636 treatment increases the level of the autophagosomal marker protein LC3-II.
[Definition]

ChEBI: 6-amino-N-[3-[4-(4-morpholinyl)-2-pyrido[2,3]furo[2,4-b]pyrimidinyl]phenyl]-3-pyridinecarboxamide is an aromatic amide.
[General Description]

A cell-permeable pyridofuropyrimidine compound that selectively inhibits mammalian type III PtdInsP kinase (IC50 = 33 nM and >5 μM using murine PIKfyve and yeast Fab1, respectively), while exhibiting much reduced activity against p110α (IC50 = 3.3 μM) and little activity against type IIγ PtdInsP kinase even at concentrations as high as 10 μM. Shown to block serum-induced PtdIns(3,5)P2 production in NIH3T3 cells (80% inhibition at 800 nM) and disrupt cellular endosomal transport in a reversible manner.
[Biological Activity]

ym201636 is a potent, selective and cell-permeable inhibitor of mammalian class iii phosphatidylinositol phosphate kinase pikfyve with ic50 value of 33nm [1].the pyridofuropyrimidine compound, ym201636, is a small-molecule inhibitor of pikfyve. in the in vitro assay, it inhibits pikfyve with ic50 value of 33nm and shows no inhibition of yeast orthologue of pikfyve. it inhibits ptdins3p p110α and type iα ptdinsp kinase with ic50 values of 3μm and > 2μm, respectively. the type iiγ ptdinsp kinase is found to be insensitive to ym201636. in serum-starved nih3t3 cells, ym201636 inhibits ptdins (3, 5) p2 production by 80% at concentration of 800nm. acute treatment of ym201636 to mefs, mdck, mcf10a, cos7 and nih3t3 cells causes the formation of large vesicular structures. besides that, ym201636 is also found to reduce the akt phosphorylation and glut4 cell surface translocation through inhibiting the insulin-dependent class i pi 3k activation [1, 2].
[IC 50]

PIKfyve: 33 nM (IC50); p110α: 3.3 μM (IC50); Autophagy
[storage]

Store at -20°C
[References]

[1] jefferies h b j, cooke f t, jat p, et al. a selective pikfyve inhibitor blocks ptdins (3, 5) p2 production and disrupts endomembrane transport and retroviral budding. embo reports, 2008, 9(2): 164-170.
[2] ikonomov o c, sbrissa d, shisheva a. ym201636, an inhibitor of retroviral budding and pikfyve-catalyzed ptdins (3, 5) p2synthesis, halts glucose entry by insulin in adipocytes. biochemical and biophysical research communications, 2009, 382(3): 566-570.
Spectrum DetailBack Directory
[Spectrum Detail]

6-Amino-N-[3-[4-(4-morpholinyl)pyrido[3',2':4,5]furo[3,2-d]pyrimidin-2-yl]phenyl]-3-pyridinecarboxamide(371942-69-7)1HNMR
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