Decitabine, Dezocitidine, AzadC, DAC, NSC-127716, Dacogen, -Drug Synthesis Database

【结构式】

【药物名称】Decitabine, Dezocitidine, AzadC, DAC, NSC-127716, Dacogen

【化学名称】5-Aza-2'-deoxycytidine
　　　　　　4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one

【CA登记号】2353-33-5

【分子式】C₈H₁₂N₄O₄

【分子量】228.20924

【开发单位】SuperGen (Orphan Drug), Pharmachemie (Originator), SuperGen (Licensee), Cancer Research UK (Codevelopment)

【药理作用】Antianemics, Colorectal Cancer Therapy, HEMATOLOGIC DRUGS, Hematopoiesis Disorders Therapy, Leukemia Therapy, Lung Cancer Therapy, Melanoma Therapy, Multiple Myeloma Therapy, Myelodysplastic Syndrome Therapy, Myeloid Leukemia Therapy, Non-Small Cell Lung Cancer Therapy, Oncolytic Drugs, Ovarian Cancer Therapy, Renal Cancer Therapy, Sickle Cell Anemia, Agents for, Solid Tumors Therapy, Antimetabolites, DNA Methyltransferase Inhibitors

合成路线1 合成路线2

合成路线1

参考文献中间体

【1】 BerrHattar J, Jiricny J. 1986. An improved syntbesis of 2'-deoxy5-azacytidine by condensation of an 9-flu-orenylmethoxycarbonyl-protected sug:ar onto the silylated base. J Org Chem, 51r 3211 --3213

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	66254	(3S,5S)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3-ol	C₆H₁₂O₄	详情	详情
(II)	66255	((2S,4S)-2-((((9H-fluoren-9-yl)peroxy)carbonyl)oxy)-4-methoxycyclopentyl)methyl 9H-fluoren-9-yl carbonoperoxoate	C₃₅H₃₀O₉	详情	详情
(III)	66256	((1R,4R)-2-((((9H-fluoren-9-yl)peroxy)carbonyl)oxy)-4-chlorocyclopentyl)methyl 9H-fluoren-9-yl carbonoperoxoate	C₃₄H₂₇ClO₈	详情	详情
(IV)	11626	N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-1,3,5-triazin-2-amine; N-(Trimethylsilyl)-N-[4-[(trimethylsilyl)oxy]-1,3,5-triazin-2-yl]amine	C₉H₂₀N₄OSi₂	详情	详情
(V)	66257	((2R,4R)-2-((((9H-fluoren-9-yl)peroxy)carbonyl)oxy)-4-(4-amino-2-oxo-1,3,5-triazin-1(2H)-yl)cyclopentyl)methyl 9H-fluoren-9-yl carbonoperoxoate	C₃₇H₃₀N₄O₉	详情	详情
(VI)	66142		C₃₇H₃₀N₄O₉	详情	详情

合成路线2

By condensation of silylated dihydro-s-triazine with deoxyribosyl chloride, catalyzed by SnCl4.

参考文献中间体

【1】 Piskala, A.; Synackova, M.; Tomankova, H.; Fiedler, P.; Zizkovsky; Direct synthesis of 5-azapyridine 2'-deoxyribonucleosides. Hydrolysis of 5-aza-2'-deoxycytidine. Nucl Acid Res 1978, 54, 109-13.
【2】 Vrijhof, W.P.; De Vos, D.; DECITABINE. Drugs Fut 1990, 15, 1, 19.

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)	11625	(2R,3S,5S)-5-Chloro-2-(methoxymethyl)tetrahydro-3-furanyl methyl ether; (2R,3S,5S)-5-Chloro-3-methoxy-2-(methoxymethyl)tetrahydrofuran		C₇H₁₃ClO₃	详情	详情
(II)	11626	N-(Trimethylsilyl)-4-[(trimethylsilyl)oxy]-1,3,5-triazin-2-amine; N-(Trimethylsilyl)-N-[4-[(trimethylsilyl)oxy]-1,3,5-triazin-2-yl]amine		C₉H₂₀N₄OSi₂	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)