Seliciclib

Base Information

• Chemical Name: Seliciclib
• CAS No.: 186692-46-6
• Molecular Formula: C19H26N6O
• Molecular Weight: 354.455
• Hs Code.: 29335990
• NSC Number: 701554
• UNII: 0ES1C2KQ94
• DSSTox Substance ID: DTXSID20171928
• Nikkaji Number: J823.057I
• Wikipedia: Seliciclib
• Wikidata: Q3494619
• NCI Thesaurus Code: C62783
• Pharos Ligand ID: LJZK33X2C6LP
• Metabolomics Workbench ID: 123527
• ChEMBL ID: CHEMBL14762
• Mol file: 186692-46-6.mol

Synonyms:(2R)-2-((6-benzylamino-9-(propan-2-yl)-9h-purin-2-yl)amino)butan-1-ol;2-(1-ethyl-2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine;CYC 202;CYC-202;CYC202;R roscovitine;R-roscovitine;roscovitine;Seliciclib

Chemical Property of Seliciclib

Chemical Property:

• Appearance/Colour: White to off-white solid.
• Vapor Pressure: 3.52E-14mmHg at 25°C
• Melting Point: 106～107℃
• Refractive Index: 1.643
• Boiling Point: 577.5 °C at 760 mmHg
• PKA: 14.56±0.10(Predicted)
• Flash Point: 303.1 °C
• PSA: 87.89000
• Density: 1.25 g/cm³
• LogP: 3.34810
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 10 mg/ml, with warming) or in Ethanol (up to 10 mg/ml).
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 354.21680947
• Heavy Atom Count: 26
• Complexity: 417

Purity/Quality:

99% ^*data from raw suppliers

Roscovitine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(CO)NC1=NC(=C2C(=N1)N(C=N2)C(C)C)NCC3=CC=CC=C3
• Isomeric SMILES: CC[C@H](CO)NC1=NC(=C2C(=N1)N(C=N2)C(C)C)NCC3=CC=CC=C3
• Recent ClinicalTrials: Multicenter Study of Seliciclib (R-roscovitine) for Cushing Disease
• Recent EU Clinical Trials: A Phase II, dose ranging, multicenter, double-blind, placebo controlled study to evaluate safety and efficacy of (R)-roscovitine in subjects with Cystic Fibrosis, homozygous for the F508del-CFTR mutation and chronically infected with Pseudomonas aeruginosa, a study involving 36 CF patients (24 treated, 12 controls).
• Description: Roscovitine (186692-46-6) is a potent and selective inhibitor of cyclin-dependent kinases displaying higher potency and selectivity compared to olomoucine. ?p34 cdc2 IC50 = 0.2 μM.? Also inhibits p33cdk2 and p33cdk5.1? Anti-angiogenic.2 Prevents PPARg S273 phosphorylation, promoting browning of white adipose tissue.3 Enhances peripheral nerve regrowth.4
• Uses: 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 c ancer (NSCLC), leukemia, HIV infection, herpes simplex infection, and the mechanisms of chronic inflammation disorders. 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.

Technology Process of Seliciclib

There total 6 articles about Seliciclib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

N-benzyl-2-fluoro-9-isopropyl-purin-6-amine (482615-52-1) + (2R)-2-aminobutan-1-ol (5856-63-3) → roscovitine (186692-46-6,186692-45-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; butan-1-ol; at 140 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.08.051

Reference yield: 89.0%

(2R)-2-aminobutan-1-ol (5856-63-3) + 2-chloro-6-phenylmethylamino-9-iso-propylpurine (186692-41-1) → roscovitine (186692-46-6,186692-45-5)

Guidance literature:

at 160 ℃; for 8h; Inert atmosphere; Large scale reaction;

DOI:10.1021/op800284k

Reference yield:

N6-benzyl-2-chloroadenine (39639-47-9) → roscovitine (186692-46-6,186692-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / K₂CO₃ / dimethylsulfoxide

2: 62 percent / 3 h / 155 - 160 °C

With potassium carbonate; In dimethyl sulfoxide;

DOI:10.1021/jm960666x

upstream raw materials:

(2R)-2-aminobutan-1-ol

2-chloro-6-phenylmethylamino-9-iso-propylpurine

N⁶-benzyl-2-chloroadenine

N-benzyl-2-fluoro-9H-purin-6-amine

Downstream raw materials:

(2R)-2-[[6-benzylamino-9-isopropyl-9H-purin-2-yl]amino]butyl 4-(nitrooxy)-butanoate

Refernces

• 1、 Oumata, Nassima,Ferandin, Yoan,Meijer, Laurent,Galons, Herve. "Practical synthesis of roscovitine and CR8". experimental part. p. 641 - 644. Retrieved 2010/04/22.
• 2、 Wang, Shudong,McClue, Steven J.,Ferguson, John R.,Hull, Jonathan D.,Stokes, Steven,Parsons, Simon,Westwood, Robert,Fischer, Peter M.. "Synthesis and configuration of the cyclin-dependent kinase inhibitor roscovitine and its enantiomer". . p. 2891 - 2894. Retrieved 2007/10/03.