CPFPX, -Drug Synthesis Database

【结构式】

【药物名称】CPFPX

【化学名称】8-Cyclopentyl-3-(3-fluoropropyl)-1-propyl-3,7-dihydro-1Hpurine- 2,6-dione

【CA登记号】

【分子式】C₁₆H₂₃FN₄O₂

【分子量】322.38571

【开发单位】Forschungszentrum Jülich; Ruprecht-Karls Universit?t Heidelberg, Heidelberg (DE); University of South Florida, Tampa, FL (US)

【药理作用】DIAGNOSTIC AGENTS

合成路线1 合成路线2

合成路线1

The cyclization of N-benzyl-N'-propylurea (I) with cyanacetic acid (II) in hot acetic anhydride gives 6-amino-1-benzyl-3-propyluracil (III), which is nitrosated with NaNO2/acetic acid and reduced with sodium dithionite to yield 5,6-diamino-1-benzyl-3-propyluracil (IV). The cyclization of (IV) with cyclopentylcarbonyl chloride (V) by means of NaOH in refluxing ethanol affords 3-benzyl-8-cyclopentyl-1-propylxanthine (VI), which is acylated with pivaloyl chloride (VII)/Na2CO3 in DMF giving the expected 7-acyl derivative (VIII). The debenzylation of (VIII) by hydrogenation over Pd/C as usual yields 8-cyclopentyl-7-pivaloyl-1-propylxanthine (IX), which is condensed with 1-bromo-3-fluoropropane (X) by means of Na2CO3 in DMF to afford 8-cyclopentyl-3-(3-fluoropropyl)-7-pivaloyl-1-propylxanthine (XI). Finally, this compound is deprotected with NaOH in DMSO/water.

参考文献中间体

【1】 Holschbach, M.H.; et al.; A1 adenosine receptor antagonists as ligands for positron emission tomography (PET) and single-photon emission tomography (SPET). J Med Chem 1998, 41, 4, 555.

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)	19803	N-benzyl-N'-propylurea		C₁₁H₁₆N₂O	详情	详情
(II)	12591	Cyanoacetic Acid; 2-Cyanoacetic acid	372-09-8	C₃H₃NO₂	详情	详情
(III)	19805	6-amino-1-benzyl-3-propyl-2,4(1H,3H)-pyrimidinedione		C₁₄H₁₇N₃O₂	详情	详情
(IV)	19806	5,6-diamino-1-benzyl-3-propyl-2,4(1H,3H)-pyrimidinedione		C₁₄H₁₈N₄O₂	详情	详情
(V)	19807	1,4-cyclopentadiene-1-carbonyl chloride		C₆H₅ClO	详情	详情
(VI)	19808	3-benzyl-8-cyclopentyl-1-propyl-3,7-dihydro-1H-purine-2,6-dione		C₂₀H₂₄N₄O₂	详情	详情
(VII)	13597	2,2-Dimethylpropanoyl chloride; Pivaloyl chloride	3282-30-2	C₅H₉ClO	详情	详情
(VIII)	19810	3-benzyl-8-cyclopentyl-7-(2,2-dimethylpropanoyl)-1-propyl-3,7-dihydro-1H-purine-2,6-dione		C₂₅H₃₂N₄O₃	详情	详情
(IX)	19811	8-cyclopentyl-7-(2,2-dimethylpropanoyl)-1-propyl-3,7-dihydro-1H-purine-2,6-dione		C₁₈H₂₆N₄O₃	详情	详情
(X)	19812	1-bromo-3-fluoropropane	352-91-0	C₃H₆BrF	详情	详情
(XI)	19813	8-Cyclopentyl-3-(3-fluoropropyl)-7-pivaloyl-1-propylxanthine		C₂₁H₃₁FN₄O₃	详情	详情

合成路线2

The reaction of 8-cyclopentyl-3-(3-hydroxypropyl)-1-propylxanthine (I) with Ts-Cl and TEA gives the corresponding tosylate (II), which is then radiolabeled by means of 18FK and Kryptofix to provide the target radiolabeled compound.

参考文献中间体

【1】 Morikawa, K.; Koizumi, M.; Endo, K.; Yono, T.; Mitusui, H.; Akamatsu, K.; Honda, H.; Synthesis and antitumor activity of platinum complexes (I). 106th Annu Meet Pharm Soc Jpn (Chiba) 1986, Abstr. 4E 10-2.

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)	58260	[8-cyclopentyl-3-(3-hydroxypropyl)-2,6-dioxo-1-propyl-1,2,3,6-tetrahydro-7H-purin-7-yl]methyl pivalate		C₂₂H₃₄N₄O₅	详情	详情
(II)	58261	[8-cyclopentyl-3-(3-{[(4-methylphenyl)sulfonyl]oxy}propyl)-2,6-dioxo-1-propyl-1,2,3,6-tetrahydro-7H-purin-7-yl]methyl pivalate		C₂₉H₄₀N₄O₇S	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)