10240. Seliciclib

Nomenclature

CAS number: 186692-46-6
(2R)-2-[[9-(1-Methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-1-butanol; 2-(R)-(1-ethyl-2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine; roscovitine; CYC-202.
C19H26N6O; mol wt 354.45.
C 64.38%, H 7.39%, N 23.71%, O 4.51%.

Description and references

Cyclin-dependent kinase (CDK) inhibitor. Prepn: L. Meijer et al., WO 9720842 (1997 to CNRS); eidem, US 6316456 (2001 to CNRS; Inst. Exp. Bot. Acad. Sci. Czech Repub.); L. Havlicek et al., J. Med. Chem. 40, 408 (1997) DOI PubMed. Synthesis and crystal structure: S. Wang et al., Tetrahedron: Asymmetry 12, 2891 (2001) DOI. CDK inhibition: W. F. De Azevedo et al., Eur. J. Biochem. 243, 518 (1998) DOI PubMed; and cellular effects: L. Meijer et al., ibid. 527 DOI PubMed. LC/MS/MS determn in plasma and urine: M. Vita et al., J. Chromatogr. B 817, 303 (2005) DOI PubMed. Protein binding and stability in plasma: eidem, ibid. 821, 75 (2005) DOI PubMed. Metabolism and pharmacokinetics in mice: B. P. Nutley et al., Mol. Cancer Ther. 4, 125 (2005) PubMed. Clinical evaluation in patients with solid tumors: C. Benson et al., Br. J. Cancer 96, 29 (2007) DOI PubMed.

Chemical structure

Properties

Crystals from chloroform/ethyl ether, mp 102-104°; [α]D 34.6° (c = 0.43 in chloroform) (Havlicek). Also reported as colorless crystalline solid from ethyl acetate/hexane, mp 106-108°; [α]D20 +56.3° (c = 0.56 in chloroform) (Wang). pKa 4.4.

Derivative

(2S)-Form.

Nomenclature

CAS number: 186692-45-5

Properties

Crystals from chloroform/ethyl ether, mp 118-120°; [α]D +35.3° (c = 0.57 in chloroform) (Havlicek). Also reported as colorless crystalline solid from ethyl acetate/hexane, mp 108-109°. [α]D20 56.3° (c = 0.56 in chloroform) (Wang).

Derivative

(±)-Form.

Nomenclature

CAS number: 186692-44-4

Properties

Crystals from chloroform/ethyl ether, mp 137-139°.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Cyclin-dependent Kinase Inhibitors