2'-deoxy-5-(1-hydroxyethyl)uridine | 112314-20-2

• 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: 2'-deoxy-5-(1-hydroxyethyl)uridine
• 英文别名: 5-(1-hydroxyethyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione；5-(1-hydroxyethyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 112314-20-2
• 化学式: C₁₁H₁₆N₂O₆
• 分子量: 272.258
• InChiKey: YFHOSHJWXJOKTI-BLYALZSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2E)-3-[1-(2-脱氧-BETA-D-赤式戊呋喃糖基)-1,2,3,4-四氢-2,4-二氧代-5-嘧啶基]-2-丙烯酸 在 盐酸 、 sodium hydroxide 、 sodium periodate 、 4,4'-硫联二(6-叔丁基-2-甲基苯酚) 、 水 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 211.0h， 生成 2'-deoxy-5-(1-hydroxyethyl)uridine
  参考文献：
  名称：

  5-（1-取代的乙基）尿嘧啶衍生物的合成及其一些化学和生物学性质

  摘要：

  为了获得在碱性条件下通过消除将得到2'-脱氧-5-乙烯基尿苷（VdUrd）的化合物，制备了一系列5-（1-取代的乙基）尿嘧啶衍生物。尝试获得5-（1-烷基-或-芳基-磺酰氧基）衍生物是不成功的，因为消除以得到5-乙烯基衍生物是非常容易的。5-（1-羟乙基）衍生物没有消除，但是在碱水溶液中得到了5-（1-羟乙基）尿嘧啶衍生物。VdUrd与一系列芳烃硫醇的反应得到5-（1-芳硫基乙基）-2'-脱氧尿苷。在不存在自由基抑制剂的情况下，主要是5-（2-芳硫基乙基）-2'脱氧尿苷。芳硫基化合物被氧化成相应的亚砜和砜。用叔丁醇钾在二甲基甲酰胺中处理这些5-（1-取代的）衍生物，得到VdUrd。如预期的那样，具有最高离去基团的化合物的反应速率最大。然而，在碱水溶液下，化合物产生2'-脱氧-5-（1-羟乙基）尿苷，并且在37℃下在pH 7.6下它们是稳定的。当尿嘧啶环的N-3被烷基化时，消除更快。讨论了该

  DOI：

  10.1039/p19870000457

文献信息

• Synergistic enhancement of 5-fluorouracil cytotoxicity by deoxyuridine analogs in cancer cells
  申请人：STC.UNM

  公开号：US10086010B2

  公开（公告）日：2018-10-02

  In one embodiment, the invention provides a method of treating a subject who suffers from a neoplasm (including a cancer such as a radiotherapeutic-resistant cancer) by administering to the subject a therapeutically effective amount of (a) 5-formyl-2′-deoxyuridine (fdU or foUdR) or a 5-formyl-2′-deoxyuridine derivative, optionally in combination with 5-hydroxy-2′-deoxyuridine (hUdR); and (b) at least one composition selected from the group consisting of either 5-fluorouracil (5-FU), a 5-FU prodrug (e.g. 5-fluoro-2′-deoxyuridine (FdU)) or 5-FU metabolite. In a preferred embodiment, a subject who suffers from colorectal cancer (CRC) or metastatic colorectal cancer (mCRC) is treated with a therapeutically-effective amount of fdU and either 5-FU or the 5-FU prodrug 5-fluoro-2′-deoxyuridine (FdU). Related pharmaceutical compositions are also provided.

  在一个实施方案中，本发明提供了一种治疗患有肿瘤（包括癌症，如放射治疗耐药癌症）的受试者的方法，该方法通过向受试者施用治疗有效量的(a)5-甲酰基-2′-脱氧尿苷（fdU或foUdR）或5-甲酰基-2′-脱氧尿苷衍生物，可选择与5-羟基-2′-脱氧尿苷（hUdR）结合使用；(b) 至少一种组合物，该组合物选自由 5-氟尿嘧啶（5-FU）、5-FU 原药（如例如，5-氟-2′-脱氧尿苷（FdU）或 5-FU 代谢物。在一个优选的实施方案中，用治疗有效量的fdU和5-FU或5-FU原药5-氟-2′-脱氧尿苷（FdU）治疗结直肠癌（CRC）或转移性结直肠癌（mCRC）患者。还提供了相关的药物组合物。
• Jones, A. Stanley; Slater, Martin J.; Walker, Richard T., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1325 - 1330
  作者：Jones, A. Stanley、Slater, Martin J.、Walker, Richard T.

  DOI：——

  日期：——
• JONES, A. STANLEY;SLATER, MARTIN J.;WALKER, RICHARD T., J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 6, 1325-1329
  作者：JONES, A. STANLEY、SLATER, MARTIN J.、WALKER, RICHARD T.

  DOI：——

  日期：——
• SYNERGISTIC ENHANCEMENT OF 5-FLUOROURACIL CYTOTOXICITY BY DEOXYURIDINE ANALOGS IN CANCER CELLS
  申请人：Ide Hiroshi

  公开号：US20180125875A1

  公开（公告）日：2018-05-10

  In one embodiment, the invention provides a method of treating a subject who suffers from a neoplasm (including a cancer such as a radiotherapeutic-resistant cancer) by administering to the subject a therapeutically effective amount of (a) 5-formyl-2′-deoxyuridine (fdU or foUdR) or a 5-formyl-2′-deoxyuridine derivative, optionally in combination with 5-hydroxy-2′-deoxyuridine (hUdR); and (b) at least one composition selected from the group consisting of either 5-fluorouracil (5-FU), a 5-FU prodrug (e.g. 5-fluoro-2′-deoxyuridine (FdU)) or 5-FU metabolite. In a preferred embodiment, a subject who suffers from colorectal cancer (CRC) or metastatic colorectal cancer (mCRC) is treated with a therapeutically-effective amount of fdU and either 5-FU or the 5-FU prodrug 5-fluoro-2′-deoxyuridine (FdU). Related pharmaceutical compositions are also provided.
• [EN] SYNERGISTIC ENHANCEMENT OF 5-FLUOROURACIL CYTOTOXICITY BY DEOXYURIDINE ANALOGS IN CANCER CELLS<br/>[FR] STIMULATION SYNERGIQUE DE LA CYTOTOXICITÉ DU 5-FLUOROURACILE DANS DES CELLULES CANCÉREUSES PAR DES ANALOGUES DE DÉSOXYURIDINE
  申请人：STC UNM

  公开号：WO2015142867A1

  公开（公告）日：2015-09-24

  In one embodiment, the invention provides a method of treating a subject who suffers from a neoplasm (including a cancer such as a radiotherapeutic-resistant cancer) by administering to the subject a therapeutically effective amount of (a) 5-formyl-2'-deoxyuridine (fdU or foUdR) or a 5-formyl-2'-deoxyuridine derivative, optionally in combination with 5-hydroxy-2'-deoxyuridine (hUdR); and (b) at least one composition selected from the group consisting of either 5-fluorouracil (5-FU), a 5-FU prodrug (e.g. 5- fluoro-2'-deoxyuridine (FdU)) or 5-FU metabolite. In a preferred embodiment, a subject who suffers from colorectal cancer (CRC) or metastatic colorectal cancer (mCRC) is treated with a therapeutically-effective amount of fdU and either 5-FU or the 5-FU prodrug 5-fluoro-2'- deoxyuridine (FdU). Related pharmaceutical compositions are also provided.