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Roscovitine

Roscovitine structure

CAS No:
186692-46-6
Formula:
C19H26N6O
Chemical Name:
Roscovitine
Synonyms:
1-Butanol,2-[[9-(1-methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-,(2R)-;1-Butanol,2-[[9-(1-methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-,(R)-;(2R)-2-[[9-(1-Methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-1-butanol;Roscovitine;CYC 202;R-Roscovitine;Seliciclib;2-(R)-(1-Ethyl-2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine;Roscovitin;(R)-Roscovitine;(2R)-2-[[6-(Benzylamino)-9-propan-2-ylpurin-2-yl]amino]butan-1-ol
Categories:
Biochemical Engineering > Inhibitors

Description

Roscovitine is a potent and selective CDKs inhibitor with IC50s of 0.2 μM, 0.65 μM, and 0.7 μM for CDK5, Cdc2, and CDK2, respectively.

Seliciclib is 2,6-Diaminopurine carrying benzylamino, (2R)-1-hydroxybutan-2-yl and isopropyl substituents at C-6, C-2-N and N-9 respectively. It is an experimental drug candidate in the family of pharmacological cyclin-dependent kinase (CDK) inhibitors. It has a role as an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor and an antiviral drug.|R-roscovitine (Seliciclib or CYC202) is a cyclin-dependent kinase (CDK) inhibitor that preferentially inhibits multiple enzyme targets including CDK2, CDK7 and CDK9, which alter the growth phase of treated cells. Developed by Cyclacel, seliciclib is being researched for the treatment of non-small cell lung cancer (NSCLC), leukemia, HIV infection, herpes simplex infection, and the mechanisms of chronic inflammation disorders.|Seliciclib is an orally available small molecule and cyclin-dependent kinase (CDK) inhibitor with potential apoptotic and antineoplastic activity. CDKs, serine/threonine kinases that play an important role in cell cycle regulation, are overexpressed in various malignancies. Seliciclib primarily inhibits CDK 2, 7, and 9 by competing for the ATP binding sites on these kinases, leading to a disruption of cell cycle progression. In addition, this agent seems to interfere with CDK-mediated phosphorylation of the carboxy-terminal domain of RNA polymerase II, thereby inhibiting RNA polymerase II-dependent transcription. This may lead to the down-regulation of anti-apoptotic factors, such as myeloid cell leukemia sequence 1 (Mcl-1), a protein crucial for the survival of a range of tumor cell types. The down-regulation of anti-apoptotic factors may lead to an induction of apoptosis, thereby further contributing to seliciclib's antiproliferative effects.|A purine derivative and competitive inhibitor of CYCLIN-DEPENDENT KINASES that has therapeutic potential as an antineoplastic and antiviral agent.

Roscovitine Basic Attributes

Molecular Weight：

354.45

Exact Mass：

354.45

UNII：

0ES1C2KQ94

NSC Number：

701554

DSSTox ID：

DTXSID20171928

NCI Thesaurus Code：

C62783

HScode：

2933990090

Characteristics

PSA：

87.9

XLogP3：

3.2

Appearance：

White to off-white solid.

Density：

1.3±0.1 g/cm3

Melting Point：

106-108 °C

Boiling Point：

577.5ºC at 760 mmHg

Flash Point：

303.1±32.9 °C

Refractive Index：

1.643

Storage Conditions：

−20°C

Vapor Pressure：

3.52E-14mmHg at 25°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

22-24/25

Drug Information

Drug Indication：

Investigated for use/treatment in breast cancer, lung cancer, lymphoma (unspecified), multiple myeloma, leukemia (lymphoid), and cancer/tumors (unspecified).

MeSH：

Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

MeSH Entry Terms：

(2R)-2-((6-benzylamino-9-(propan-2-yl)-9h-purin-2-yl)amino)butan-1-ol

Roscovitine Use and Manufacturing

Roscovitine is a potent and selective inhibitor of cyclin-dependent kinases (CDKs). Roscovitine has been found to produce apoptosis in treated cancerous cells of non-small cell lung cancer (NSCLC) and other cancers. Studies show that Roscovitine displays increased anti-mitotic activity at the G1/S and G2/M phases of the cell cycle. Roscovitine maybe useful in the treatment of non-small cell lung cancer (NSCLC), leukemia, HIV infection, herpes simplex infection, and the mechanisms of chronic inflammation disorders.

Computed Properties

Molecular Weight:354.4
XLogP3:3.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:8
Exact Mass:354.21680947
Monoisotopic Mass:354.21680947
Topological Polar Surface Area:87.9
Heavy Atom Count:26
Complexity:417
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Roscovitine(Seliciclib,CYC202)

CAS No.: 186692-46-6

Content: 99%

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