5'-chloro-5'-deoxy-5-fluorouridine | 66981-53-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-chloro-5'-deoxy-5-fluorouridine
• 英文别名: 5'-deoxy-5'-chloro-5-fluorouridine；5'-chloro-5-fluoro-5'-deoxy-uridine；5'-Chloro-5'-deoxy-5-fluorouridine；1-[(2R,3R,4S,5S)-5-(chloromethyl)-3,4-dihydroxyoxolan-2-yl]-5-fluoropyrimidine-2,4-dione
• CAS: 66981-53-1
• 化学式: C₉H₁₀ClFN₂O₅
• 分子量: 280.64
• InChiKey: QZPXJUSKPZADEK-UAKXSSHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-chloro-5'-deoxy-5-fluorouridine 在 sodium tetrahydroborate 、 sodium periodate 作用下， 生成 5'-chloro-5'-deoxy-5-fluoro-2',3'-secouridine
  参考文献：
  名称：

  核苷。IV。2'，3'，5'-三氯-2'，3'，5'-三苯氧基-2'，3'-水our苷的合成和反应。

  摘要：

  2', 3', 5'-Trichloro-2', 3', 5'-trideoxy-2', 3'-secouridines（2a, b）是由尿苷或 5-氟尿苷通过偏碘酸钠氧化、硼氢化钠还原和 Vilsmeier-Haack 试剂氯化组合合成的。将 2a 和 b 与碱反应，可得到一些新的嘧啶无环核苷（3-5）和（尿嘧啶-l-基）-1，4-二氧杂环（8，9）。此外，还介绍了由 5'-chloro-5'-deoxyuridine (10) 制备 5'-chloro-5'-deoxy-2', 3'-secouridine (11) 以及将其转化为 (尿嘧啶-l-基)-1, 4-二氧杂环12 和 5'-deoxy-2', 3'-secouridine (13)的方法。

  DOI：

  10.1248/cpb.36.1298

文献信息

• Synthesis and biological activity of 5'-substituted 5-fluoropyrimidine nucleosides
  作者：Sudhir Ajmera、Peter V. Danenberg

  DOI：10.1021/jm00350a024

  日期：1982.8

  5'-Deoxy-5-fluorouridine (5'-dFUrd, 1) possesses a significantly higher chemotherapeutic index than other fluoropyrimidines as a result of its being selectivity cleaved in tumors to 5-fluorouracil (FUra) by uridine phosphorylase. Because 1 is a relatively poor substrate for this enzyme, we synthesized a series of 5'-deoxy-5'-substituted-5-fluorouridine (FUrd) derivatives in an effort to obtain compounds that might have improved substrate interactions compared to 1 and thus possibly be better prodrugs of FUra. Three derivatives, 5'-O-tosyl-FUrd (13), 5'-O-mesyl-FUrd (14), and 5'-deoxy-5'-bromo-FUrd (15), had cytostatic activity against L1210 and CCRF-CEM leukemic cells in culture superior to that of 1. In preliminary in vivo antitumor studies against L1210 leukemic cells in mice, 5'-deoxy-5'-chloro-FUrd (4), 5'-O-mesyl-FUrd (14), an 5'-deoxy-5'-fluoro-FUrd (18) gave percent increases in life span of 64, 58, and 58, respectively, compared to a value of 20 for compound 1.
• Nucleosides. IV. Synthesis and reactions of 2',3',5'-trichloro-2',3',5'-trideoxy-2',3'-secouridines.
  作者：KOSAKU HIROTA、TETSUO TOMISHI、YOSHIFUMI MAKI

  DOI：10.1248/cpb.36.1298

  日期：——

  2', 3', 5'-Trichloro-2', 3', 5'-trideoxy-2', 3'-secouridines (2a, b) were synthesized from uridine or 5-fluorouridine by a combination of sodium metaperiodate oxidation, sodium borohydride reduction, and chlorination with Vilsmeier-Haack reagent. Reaction of 2a, b with base gave some new pyrimidine acyclonucleosides (3-5) and (uracil-l-yl)-1, 4-dioxanes (8, 9). The preparation of 5'-chloro-5'-deoxy-2', 3'-secouridine (11) from 5'-chloro-5'-deoxyuridine (10) and its conversion into (uracil-l-yl)-1, 4-dioxane 12 and 5'-deoxy-2', 3'-secouridine (13) are also described.

  2', 3', 5'-Trichloro-2', 3', 5'-trideoxy-2', 3'-secouridines（2a, b）是由尿苷或 5-氟尿苷通过偏碘酸钠氧化、硼氢化钠还原和 Vilsmeier-Haack 试剂氯化组合合成的。将 2a 和 b 与碱反应，可得到一些新的嘧啶无环核苷（3-5）和（尿嘧啶-l-基）-1，4-二氧杂环（8，9）。此外，还介绍了由 5'-chloro-5'-deoxyuridine (10) 制备 5'-chloro-5'-deoxy-2', 3'-secouridine (11) 以及将其转化为 (尿嘧啶-l-基)-1, 4-二氧杂环12 和 5'-deoxy-2', 3'-secouridine (13)的方法。