5-trans-propenyluracil | 132400-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-trans-propenyluracil
• 英文别名: (E)-5-propen-1-yluracil；E-5-(1-Propenyl)uracil；5-(E-propen-1-yl) uracil；5-[(E)-prop-1-enyl]-1H-pyrimidine-2,4-dione
• CAS: 132400-70-5
• 化学式: C₇H₈N₂O₂
• 分子量: 152.153
• InChiKey: PPTBYVVCEZHLQZ-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-trans-propenyluracil 生成 E-2'-deoxy-5-(propen-1-yl)-4'-thiouridine
  参考文献：
  名称：

  Antiviral pyrimidine nucleosides

  摘要：

  化学式为I的嘧啶4'-硫核苷，其中Y为羟基或氨基，X为氯、溴、碘、三氟甲基、C.sub.2-6烷基、C.sub.2-6烯基、C.sub.2-6卤代烯基或C.sub.2-6炔基及其生理功能衍生物。这些化合物具有抗病毒剂的用途。

  公开号：

  US05356882A1
• 作为产物：
  描述：

  5-丙-2-烯基-1H-嘧啶-2,4-二酮 在 Wilkinson's catalyst 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以70%的产率得到5-trans-propenyluracil
  参考文献：
  名称：

  Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides

  摘要：

  A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents. A number of analogues such as 2'-deoxy-5-propyl-4'-thiouridine (3ii), 2'-deoxy-5-isopropyl-4'-thiouridine (3iii), 5-cyclopropyl-2'-deoxy-4'-thiouridine (3iv), 2'-deoxy-4'-thio-5-vinyluridine (3viii), and 5-(2-chloroethyl)-2'-deoxy-4'-thiouridin (3xx) were found to be highly active against herpes simplex virus type-1 (HSV-1) and varicella tester virus (VZV) in vitro with no significant cytotoxicity. The compound with the broadest spectrum of activity was 2'-deoxy-5-ethyl-4'-thiouridine (3i) which showed significant activity against HSV-1, HSV-2, and VZV.

  DOI：

  10.1021/jm950029r

文献信息

• Synthesis of various 5-substituted uracils
  作者：Dan Peters、Anna-Britta Hörnfeldt、Salo Gronowitz

  DOI：10.1002/jhet.5570270756

  日期：1990.11

  Several Pd-catalyzed coupling reactions have been evaluated for the synthesis of 5-substituted uracils. A convenient reaction, further developed by us, is the Suzuki Pd(0)-catalyzed coupling between arylboronic acids and aryl bromides or iodides in weakly alkaline medium. However, all attempts to use 5-bromo- or 5-iodouracil as the aryl halide failed. On the other hand, couplings between 2,4-di-t-

  已评估了几种Pd催化的偶联反应，用于合成5取代的尿嘧啶。由我们进一步开发的一种方便的反应是在弱碱性介质中芳基硼酸与芳基溴化物或碘化物之间的Suzuki Pd（0）催化偶联。但是，所有使用5-溴-或5-碘尿嘧啶作为卤代芳基的尝试均告失败。在另一方面，2,4-二-之间的耦合吨丁氧基-5-溴嘧啶和各种芳基硼酸是成功的。在当芳基硼酸是不可用的情况下，这是更好扭转耦合功能，并使用2,4-二-吨-丁氧基-5-嘧啶硼酸和芳基溴化物。以此方式制备了大量的5-芳基尿嘧啶。它们是通过5-芳基-2,4-二-的脱烷基作用以几乎定量的产率获得的叔丁氧基嘧啶。然而，这些方法的最大缺点是2,4-二氯-5-溴嘧啶，其为2,4-二-的合成中的中间体的高过敏性质吨丁氧基-5-溴嘧啶和2,4-二Ť-丁氧基-5-嘧啶硼酸。为了避免这种中间体，尝试了5-溴-2，4-二三甲基甲硅烷基氧基嘧啶和芳基硼酸之间的偶联，但是失败了。此外，由
• Antiviral pyrimidine nucleosides and methods for using same
  申请人：University of Birmingham

  公开号：US05521163A1

  公开（公告）日：1996-05-28

  1'-Deoxy-5-ethyl-4'-thio-.beta.-uridine as a compound including its physiologically functional derivatives, pharmaceutical compositions containing it and methods of treating herpes virus infections are described.

  本文描述了1'-去氧-5-乙基-4'-硫基-β-脱氧尿嘧啶及其生理功能衍生物、含有该化合物的制药组合物以及治疗疱疹病毒感染的方法。
• Nucleoside 5'-alkyl- or alkenylphosphate
  申请人：Yamasa Shoyu Kabushiki Kaisha

  公开号：EP0097376A1

  公开（公告）日：1984-01-04

  Nucleoside 5'-alkyl- or alkenyl phosphate compounds represented by the following formula [I] wherein B is a purine base having a substituent or a 5-substituted uracil base, and R' is an alkyl or alkenyl group having 14 to 26 carbon atoms, and pharmaceutically acceptable salts thereof are novel derivatives of arabinonucleosides which can have properties suitable for clinical application as antiviral agents, particularly for treating viral hepatitis.

  由下式[I]代表的核苷 5'-烷基-或烯基磷酸酯化合物 其中 B 是具有取代基的嘌呤基或 5-取代的尿嘧啶基，R'是具有 14 至 26 个碳原子的烷基或烯基，及其药学上可接受的盐是阿拉伯核苷的新型衍生物，其特性适合作为抗病毒药物，特别是用于治疗病毒性肝炎的临床应用。
• Further antiviral pyrimidine nucleosides
  申请人：THE UNIVERSITY OF BIRMINGHAM

  公开号：EP0421777A1

  公开（公告）日：1991-04-10

  Pyrimidine 4′-thionucleosides of the formula (I) where B¹ is a pyrimidine base; and either (a) R² is hydrogen and R³ is hydroxy or fluoro, or (b) R² is hydroxy and R³ is hydrogen, hydroxy or fluoro, or (c) R² is fluoro and R³ is hydrogen or hydroxy, or (d) R² and R³ together form a carbon-carbon bond; and physiologically functional derivatives thereof and processes for their production. Preferably, the base B¹ is of the formula (II) wherein Y is hydroxy or amino, monoalkylamino or dialkylamino; and X is halogen, alkoxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, amino, monoalkylamino, dialkylamino, cyano or nitro. The compounds are useful in the treatment of viral infections.

  式(I)的嘧啶-4′-硫代核苷 其中 B¹ 是嘧啶碱； (a) R² 是氢，R³ 是羟基或氟、 或 (b) R² 是羟基，R³ 是氢、羟基或氟、 或 (c) R² 是氟，R³ 是氢或羟基、 或 (d) R² 和 R³ 共同形成碳-碳键；以及其生理功能衍生物及其生产工艺。碱 B¹ 最好为式 (II) 其中 Y 是羟基或氨基、单烷基氨基或二烷基氨基；X 是卤素、烷氧基、烷基、卤代烷基、烯基、卤代烯基、炔基、氨基、单烷基氨基、二烷基氨基、氰基或硝基。这些化合物可用于治疗病毒感染。
• Preparation of thionucleosides
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0514036A2

  公开（公告）日：1992-11-19

  The invention relates to the preparation of homochiral thiolactones which have application in the synthesis of 3′- and 4′- thionucleosides. Substituents on the thiolactone can be used to influence the configuration of the C-1′ position in the final nucleoside. Configuration at the C-4′ position is controlled by use of the appropriate homochiral glycidol as starting material in the synthesis of the thiolactone. This process also offers the possibility of introducing substituents diastereoselectively in the C-2′ and C-3′ positions.

  本发明涉及同手性硫代内酯的制备，它可应用于 3′-和 4′-硫代核苷的合成。硫内酯上的取代基可用来影响最终核苷中 C-1′ 位的构型。在合成硫代内酯的过程中，使用适当的同手性缩水甘油作为起始原料，可以控制 C-4′ 位的构型。这一过程还提供了在 C-2′ 和 C-3′ 位非对映选择性引入取代基的可能性。