(R)-Roscovitine, CYC-202, Seliciclib, -Drug Synthesis Database

【结构式】

【药物名称】(R)-Roscovitine, CYC-202, Seliciclib

【化学名称】6-(Benzylamino)-2-[1(R)-(hydroxymethyl)propylamino]-9-isopropylpurine

【CA登记号】186692-46-6

【分子式】C₁₉H₂₆N₆O

【分子量】354.45867

【开发单位】CNRS (Originator), Institute of Cancer Research (Originator), Cyclacel (Licensee)

【药理作用】Breast Cancer Therapy, Lung Cancer Therapy, Nephritis, Agents for, Non-Small Cell Lung Cancer Therapy, Oncolytic Drugs, RENAL-UROLOGIC DRUGS, Treatment of Renal Diseases, Apoptosis Inducers, CDK1 Inhibitors, CDK2 Inhibitors, CDK7 Inhibitors, CDK9 Inhibitors, ERK2 Inhibitors, Inhibitors of Signal Transduction Pathways

合成路线1

Condensation of 2,6-dichloropurine (I) with benzylamine (II) in boiling butanol afforded 6-(benzylamino)-2-chloropurine (III), which was subsequently alkylated at the 9-N with isopropyl bromide (IV), yielding purine (V). The 2-chloro group was finally displaced with (R)-2-amino-1-butanol (VI) in a sealed tube at 160 C to provide the title compound.

参考文献中间体

【1】 Wang, S.; et al.; Synthesis and configuration of the cyclin-dependent kinase inhibitor roscovitine and its enantiomer. Tetrahedron Asymmetry 2001, 12, 20, 2891.
【2】 Havlicek, L.; et al.; Cytokinin-derived cyclin-dependent kinase inhibitors: Synthesis and cdc2 inhibitory activity of olomoucine and related compounds. J Med Chem 1997, 40, 4, 408.
【3】 Meijer, L.; Bisagni, E.; Legraverend, M. (CNRS (Centre National de la Recherche Scientifique)); Novel purine derivs. having, in particular, antiproliferative properties, and biological uses thereof. EP 0874847; FR 2741881; JP 2000501408; US 2002049218; US 6316456; WO 9720842 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	25254	2,6-dichloro-9H-purine	5451-40-1	C₅H₂Cl₂N₄	详情	详情
(II)	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情
(III)	36315	N-benzyl-2-chloro-9H-purin-6-amine; N-benzyl-N-(2-chloro-9H-purin-6-yl)amine		C₁₂H₁₀ClN₅	详情	详情
(IV)	32658	2-bromopropane	75-26-3	C₃H₇Br	详情	详情
(V)	36316	N-benzyl-2-chloro-9-isopropyl-9H-purin-6-amine; N-benzyl-N-(2-chloro-9-isopropyl-9H-purin-6-yl)amine		C₁₅H₁₆ClN₅	详情	详情
(VI)	48572	(S)-(+)-2-Amino-1-butanol; L-(+)-2-Amino-1-butanol; (S)-2-Amino-1-butanol	5856-62-2	C₄H₁₁NO	详情	详情

Extended Information