3'-O-benzoyl-5-fluoro-2'-deoxyuridine | 1995-83-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-O-benzoyl-5-fluoro-2'-deoxyuridine
• 英文别名: [(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 1995-83-1
• 化学式: C₁₆H₁₅FN₂O₆
• 分子量: 350.303
• InChiKey: WINHOLWWINLHRE-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-O-benzoyl-5-fluoro-2'-deoxyuridine 在 三甲基氯硅烷 、 亚磷酸二苯酯 、 sulfur 、 三乙胺 、 甲胺 作用下， 以 吡啶 、 水 为溶剂， 反应 1.42h， 生成 ammonium 5-fluoro-2'-deoxyuridin-5'-yl phosphorothioate
  参考文献：
  名称：

  Nucleoside H-Phosphonates. 18. Synthesis of Unprotected Nucleoside 5‘-H-Phosphonates and Nucleoside 5‘-H-Phosphonothioates and Their Conversion into the 5‘-Phosphorothioate and 5‘-Phosphorodithioate Monoesters

  摘要：

  A simple and efficient protocol for the preparation of unprotected nucleoside 5'-H-phosphonates and nucleoside 5'-H-phosphonothioates via a one-step deprotection of suitable precursors with methylamine has been developed. The synthetic utility of the unprotected nucleotide derivatives was demonstrated by converting them under mild conditions to the corresponding nucleoside 5'-phosphorothioate and nucleoside 5'-phosphorodithioate monoesters. Factors affecting oxidation of H-phosphonate, H-phosphonothioate, and phosphite derivatives with elemental sulfur are also discussed.

  DOI：

  10.1021/jo980491u
• 作为产物：
  描述：

  5-氟-2'-脱氧脲核苷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 3'-O-benzoyl-5-fluoro-2'-deoxyuridine
  参考文献：
  名称：

  针对脱唾液酸糖蛋白受体介导的5-氟-2'-脱氧尿苷肝细胞癌的研究

  摘要：

  抗癌核苷5-氟2'-脱氧尿苷-5'-磷酸（5-FdU-P）通过酰胺链接头连接到三天线GalNAc簇上，作为将药物递送到识别氨基糖单元的肝细胞的一种手段。

  DOI：

  10.1016/j.bmcl.2018.06.002

文献信息

• WATER-SOLUBLE CAMPTOTHECIN DERIVATIVE, PHARMACEUTICAL COMPOSITION AND USE THEREOF
  申请人：Zhou Wenqiang

  公开号：US20140155336A1

  公开（公告）日：2014-06-05

  The present invention relates to a water soluble derivative of camptothecin and preparation method thereof, the derivative having a structure of formula I and being appropriate in water solubility, and having anti-cancer activity and stability of lactonic ring. The present invention also relates to a method for synthesizing the compound and medical use of the compound.

  本发明涉及一种水溶性紫杉醇衍生物及其制备方法，所述衍生物具有式I的结构，在水溶性方面适宜，并具有抗癌活性和内酯环的稳定性。本发明还涉及一种合成该化合物的方法以及该化合物的医药用途。
• New 3′-O-aromatic acyl-5-fluoro-2′-deoxyuridine derivatives as potential anticancer agents
  作者：Agnieszka Szymańska-Michalak、Dariusz Wawrzyniak、Grzegorz Framski、Marta Kujda、Paulina Zgoła、Jacek Stawinski、Jan Barciszewski、Jerzy Boryski、Adam Kraszewski

  DOI：10.1016/j.ejmech.2016.03.010

  日期：2016.6

  New aromatic and aliphatic 3'-O-acyl-5-fluoro-2'-deoxyuridine derivatives were synthesized and evaluated as candidates for prodrugs against various cancer cell lines. As the most promising candidate for antimalignant therapeutics was found a dual-acting acyl derivative 7h, which apparently released not only the known anticancer nucleoside, 5-fluoro-2'-deoxyuridine (FdU), but also an additional active

  合成了新的芳香族和脂肪族3'-O-酰基-5-氟-2'-脱氧尿苷衍生物，并将其评估为针对各种癌细胞系的前药候选物。作为抗肿瘤治疗的最有希望的候选者，发现了一种双作用酰基衍生物7h，它不仅释放出已知的抗癌核苷5-氟-2'-脱氧尿苷（FdU），而且还释放了另外的活性代谢产物乙酰水杨酸，从而增强FdU的治疗效果。有希望的治疗指数还显示了一些装饰有FdU酯的芳香族二羧酸衍生物（11和12）。
• Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: enzyme substrate recognition
  作者：Ning Li、Min-Hua Zong、Ding Ma

  DOI：10.1016/j.tet.2008.11.045

  日期：2009.1

  The substrate recognition of Pseudomonas cepacia lipase in the acylation of nucleosides was investigated by means of rational substrate engineering for the first time. P. cepacia lipase displayed excellent 3′-regioselectivities (96 to >99%) in the lauroylation of 2′-deoxynucleosides 1a–1e, while low to good 3′-regioselectivities (59–89%) in the lauroylation of ribonucleosides 1f–1j. It might be due

  首次通过合理的底物工程研究了假单胞菌脂肪酶在核苷酰化中的底物识别。P. cepacia脂肪酶在2'-脱氧核苷1a - 1e的月桂酰化中显示出极好的3'-区域选择性（96至> 99％），而在核糖核苷1f -12的月桂酰化中显示低至良好的3'-区域选择性（59-89％）。1J。这可能是由于1f – 1j的2'-羟基之间不利的氢键相互作用酪氨酸残基中的酪氨酸残基和酚羟基存在于酶的另一个疏水口袋中，可稳定5'-酰化过渡态的构象，从而增加次要区域异构体的数量。此外，脂肪酶成功地合成了氟尿苷的各种酯衍生物，其转化率高（99％），并且在温和条件下具有良好至优异的3'-区域选择性。检查了酶对各种酰基供体的识别。根据脂肪酶活性位点的结构，尤其是大小，形状和理化性质，对酰基的酶促识别是合理的。
• WATER SOLUBLE CAMPTOTHECIN DERIVATIVE, PHARMACEUTICAL COMPOSITION AND USE THEREOF
  申请人：Hunan Fangshenghuamei Medical Tech. Co., Ltd.

  公开号：EP2738176B1

  公开（公告）日：2016-11-16
• Nucleoside <i>H</i>-Phosphonates. 18. Synthesis of Unprotected Nucleoside 5‘-<i>H</i>-Phosphonates and Nucleoside 5‘-<i>H</i>-Phosphonothioates and Their Conversion into the 5‘-Phosphorothioate and 5‘-Phosphorodithioate Monoesters
  作者：Jadwiga Jankowska、Anna Sobkowska、Jacek Cieślak、Michał Sobkowski、Adam Kraszewski、Jacek Stawiński、David Shugar

  DOI：10.1021/jo980491u

  日期：1998.11.1

  A simple and efficient protocol for the preparation of unprotected nucleoside 5'-H-phosphonates and nucleoside 5'-H-phosphonothioates via a one-step deprotection of suitable precursors with methylamine has been developed. The synthetic utility of the unprotected nucleotide derivatives was demonstrated by converting them under mild conditions to the corresponding nucleoside 5'-phosphorothioate and nucleoside 5'-phosphorodithioate monoesters. Factors affecting oxidation of H-phosphonate, H-phosphonothioate, and phosphite derivatives with elemental sulfur are also discussed.