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氮杂胞苷的合成工艺研究 被引量：4

Improved synthesis of azacytidine
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摘要 以氰基胍和甲酸为原料,经成盐、环合反应得到5-氮杂胞嘧啶,5-氮杂胞嘧啶经硅烷化保护后,与乙酰化的核糖成苷,再脱保护基得到氮杂胞苷。目标化合物的结构经1H-NMR、MS谱数据确证,总收率为26.6%。该工艺路线优化了反应条件、简化了操作、提高了收率。 Cyanoguanidine and acetylated β-D-ribose were used as starting materials to give target compound via salt formation, cyclization, silylation, coupling reaction and deprotection. The target compound was characterized by ^1H-NMR, MS spectra and the total yield was 26.6 %. The synthetic conditions were optimized and the total yield was increased.
作者 郭刚 杨千姣 赵力挥 刘丹 赵临襄
机构地区 沈阳药科大学制药工程学院
出处 《中国药物化学杂志》 CAS CSCD 2008年第5期377-378,383,共3页 Chinese Journal of Medicinal Chemistry
基金 国家自然科学基金海外青年学者合作研究基金项目(30328030)
关键词 工艺改进 化学合成 氮杂胞苷 氰基胍 process improvement chemical synthesis azacytidine cyanoguanidine
分类号 TQ463 [化学工程—制药化工]
  • 相关文献

参考文献9

  • 1WINKLEY M W, ROBONS R K. Direct glycosylation of 1,3, 5-triazinones. A new approach to the synthesis of the nucleoside antibiotic 5-azacytidine(4-amino-1-β- D-ribofuranosyl-1, 3, 5-triazin-2-one )and rented derivatives[J] .J Org Chem, 1970, 35(2) :491 - 495.
  • 2PISLALA A. Nucleic acid components and their analogues. Cl. Synthesis of 5-azacytosine(4-amino-1, 2- dihydro-1, 3, 5-triazin-2-one) and its methyl derivatives[J]. Collection Czechoslov Chem Commun, 1967, 32(11) :3966 - 3976.
  • 3NIEDBALLA U, VORBRUGGEN H. A general synthesis of N-glycoside. V. Synthesis of 5-azacytidines [J].J Org Chem, 1974, 39(25) :3672 - 3674.
  • 4HARTENSTEIN R, FRIDOVICH I. Amidinourea formate, a precursor of 2-amino-4-hydroxyl-s-triazine [J] .J Org Chem, 1967, 32(5) : 1653 - 1654.
  • 5张文生,申艳红,刘启宾,冯峰,渠桂荣.5-氮杂胞嘧啶的合成研究[J].武汉大学学报（理学版）,2003,49(4):454-456. 被引量：2
  • 6HANNA N B, ZAJICEK J, PISKALA A. 6-Methyl-5- azactidine-synthesis, conformational properties and biological activity. A comparision of molecular conformation with 5-azacytidine [ J ]. Nueleosides Nucleotides, 1997,16(1/2) : 129 - 144.
  • 7LIN K T, MOMPARLER R L, RIVARD G. High-performance liquid chromatographic analysis of chemical stability of 5-aza-2'-deoxycytidine[J]. J Pharm Sci, 1981, 70(11) : 1228 - 1232.
  • 8VORBRUGGEN H, HOFLE G. On the mechanism of nucleoside synthesis[J]. Chem Ber, 1981, 114:1256 - 1268.
  • 9DUMITRU I, ANN A, PETE B. Synthesis of 5-azacytidine: US, 7038038[P], 2006 - 03 - 02.

二级参考文献10

  • 1Hakimelahi G H, Zarrinehzad M, Jarrahpour A A, et al. Ring Open Analogues of Adenine Nucleosode.Aminoacyl Derivatives of Cyclo- and Acyclo-Nucleo-sides [J]. Helvetica Chimica,1987,70(1): 219-231.
  • 2Wu G H, Mitra K A. Synthesis of Acyclovir Ganciclovir and Their Prodangs: A Review[J]. Synthesis,2000,3: 329-351.
  • 3Boryski J, Golankiewicz B. A Facile Synthesis of 9-(1,3-Dihydroxy-2-Propoxymethyl) Guanosine (Ganciclovir) from Guanosine [J]. Synthesis, 1999, 4: 625-628.
  • 4Morris J R, Perter H W, Balzarini J, et al. Nucleic Acid Related Compounds, 47. Synthesis and Biological Activities of Pyrimidine and Purine "Acyclic" Nucleoside Analogues [J]. J Med Chem, 1984, 27: 1486-1492.
  • 5Nair V, Nuesca Zoraida M. Isodideoxy Nucleosides: A Conceptually New Class of Nucl-Eoside Antiviral Agents [J]. J Am Chem Soc , 1992, 114: 7951-7953.
  • 6George B, S. Welliky V. 2-Chloroadenine and 2-Chloroadenosine [J]. J Org Chem, 1958, 23: 125-126.
  • 7Vesely J, Cihak A. High-frequency Induction in Vivo of Mouse Leukemia in AKR Strain by 5-Azacytidine and 5-Iodo-2-Deoxyuridine [J]. Experientia, 1973,29(9): 1132-1133.
  • 8Piskala A. Nucleic Acid Components and Their Analogues. CI. Synthesis of Dihydro-1,3,5- Triazin-2-One and Its Derivatives [J]. Collection Czechslov Chem Commun, 1976, 32 : 3966-3976.
  • 9Niedballa U, Vobr H. A General Synthesis of N-glycosides V.Synthesis of 5-Azacytidines [J].J Org Chem, 1974,39(25) : 3762-3764.
  • 10Pankiewicz K W . Fluorinated Nucleosides [J]. Carbohydrate Res, 2000, 327 : 87-105.

共引文献1

同被引文献73

  • 1祝丽华,陈茜,徐云峰,范举正.1,3,5-三-苯甲酰基-2-去氧-2-氟-β-D-核糖的合成[J].华西药学杂志,2005,20(3):207-210. 被引量：5
  • 2余建鑫,张万年,姚建忠,宋云龙,盛春泉.抗肿瘤药物卡培他滨的合成工艺改进[J].中国药物化学杂志,2005,15(3):173-175. 被引量：21
  • 3杨晓,朱珠,单秀英.治疗骨髓发育不良综合征新药——阿扎胞苷[J].中国药学杂志,2006,41(9):717-718. 被引量：3
  • 4杨薇,陈银海,崔恒宓.地西他滨和5-阿扎胞苷在癌症研究及临床上的应用[J].中国药学杂志,2006,41(21):1601-1605. 被引量：5
  • 5Yang Xiaojing, Lay F, Han Han, et al. Targeting DNA methy- lation for epigenetie therapy[J]. Trends in Phatmaeologieal Sci- ences,2010,31 (11) :536-546.
  • 6Limontav M, Colombo T, Damia G, et a l. Cytotoxic activity and mechanism of action of 5-aza-2deoxycytidine in human CMLcells[J]. Leukemia Research, 1993,17(11) : 977-982.
  • 7Zielinski W S, Sprinzl M. Chemical synthesis of 5-azacytidine nucleotides and preparation of tRNAs containing 5-azacytidine in its 3'-terminus[J]. Nucleic Acids Research, 1984,12 (12) : 5025-5036.
  • 8Okuyama K,Noguchi T. Molecular cloning and expression of the nucleoside deoxyribosyltransferase-II gene from Lactoba- cillushelveticus[J]. Biosci Biotechnol Biochem,2000,64(10): 2243-2245.
  • 9Miyamoto Y, Masaki T, Chohnan S. Characterization of N- deoxyrihosyl-transferase from Lactococcus lactis suhsp, lactis[J]. Biochimica et Biophysica Acta, 2007, 1774 (10) : 1323- 1330.
  • 10Uerkvitz W. Trans-N-deoxyribosylase from Lactobacillus hel- veticus crystallization and properties[J]. European Journal of Biochemistry, 1971,23(2) :387-395.

引证文献4

二级引证文献9

中国药物化学杂志
2008年 第5期

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