Roscovitine (R)-2-((6-(苄基氨基)-9-异丙基-9H-嘌呤-2-基)氨基)丁-1-醇

CAS 186692-46-6 MFCD02266401

化学结构图

186692-46-6
SMILES: CC[C@H](CO)Nc1nc(NCc2ccccc2)c2ncn(C(C)C)c2n1

化学属性

Mol. FormulaC19H26N6O
Mol. Weight354
Density1.3
Boiling Point577.5
Melting Point106-107
Appearance Solid powder
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical NameRoscovitine
Synonym 2-(R)-[[9-(1-Methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-1-butanol 6-(Benzylamino)-2(R)-[[1-(hydroxymethyl)propyl]amino]-9-isopropylpurine CYC202; CYC202; CYC 202; R-Roscovitine; Roscovitin; Roscovitine; Seliciclib.
MDL NumberMFCD02266401
PubChem Substance ID24278682
CAS Number186692-46-6
Chemical Name Translation(R)-2-((6-(苄基氨基)-9-异丙基-9H-嘌呤-2-基)氨基)丁-1-醇
FormulaC19H26N6O
IUPAC Name(R)-2-((6-(benzylamino)-9-isopropyl-9H-purin-2-yl)amino)butan-1-ol
InChIKeyBTIHMVBBUGXLCJ-OAHLLOKOSA-N
InChIInChI=1S/C19H26N6O/c1-4-15(11-26)22-19-23-17(20-10-14-8-6-5-7-9-14)16-18(24-19)25(12-21-16)13(2)3/h5-9,12-13,15,26H,4,10-11H2,1-3H3,(H2,20,22,23,24)/t15-/m1/s1
Canonical SMILESCC[C@@H](NC1=NC(NCC2=CC=CC=C2)=C3N=CN(C(C)C)C3=N1)CO
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分类

  • {SA} A to C, Antitumor Agents, Apoptosis and Cell Cycle, Bioactive Small Molecules, Biochemicals and Reagents, Cancer Research, Cell Biology, Cell Cycle Proteins and Antibodies, Cell Cycle Regulators, Cell Signaling and Neuroscience, Cyclin Dependent Kinases, Cyclin-Dependent Kinase (CDK), Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, Kinase/Phosphatase Biology, R, Serine/Threonine Kinase Biology, Serine/Threonine Kinase Inhibitors
  • {SNA} A to C, Antitumor Agents, Apoptosis and Cell Cycle, Bioactive Small Molecules, Biochemicals and Reagents,
  • {SNA} A to C,

产品应用

  • Seliciclib, also known as roscovitine and CYC202, is a n orally bioavailable, small-molecule cyclin-dependent kinase (CDK) inhibitor with potential proapoptotic and antineoplastic activities. Seliciclib primarily inhibits CDK2/E, CDK2/A, CDK7 and CDK9 by competing for their ATP binding sites, leading to a disruption of cell cycle progression. In addition, this agent appears to interfere with CDK-mediated phosphorylation of the carboxy-terminal domain of RNA polymerase II, inhibiting RNA polymerase II-dependent transcription, which may result in the down-regulation of antiapoptotic proteins such as induced myeloid leukemia cell differentiation protein Mcl-1.

相关文献及参考

  • DeAzevado, W.F., et al., Inhibition of cyclin-dependent kinases by purine analogues: crystal structure of human cdk2 complexed with roscovitine. Eur. J. Biochem. 243 , 518-526, (1997) 摘要
  • Chen, M.C., et al., Involvement Of CAMP In Nerve Growth Factor-triggered P35/Cdk5 Activation And Differentiation In PC12 Cells. Am. J. Physiol. Cell Physiol. 299 , C516-27, (2010) 摘要
  • Merck 14 ,10240

安全信息

WGK Germany3
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
GHS Symbol
Safety Statements
Precautionary statements
Storage condition Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

系列性分类


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