(E)-3-(thymin-1'-yl)propenal | 79251-82-4

• 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: (E)-3-(thymin-1'-yl)propenal
• 英文别名: trans-thymine propenal；trans-1-(3-Oxoprop-1-enyl)thymine；thymine propenal；(E)-3-(5-methyl-2,4-dioxopyrimidin-1-yl)prop-2-enal
• CAS: 79251-82-4
• 化学式: C₈H₈N₂O₃
• 分子量: 180.163
• InChiKey: CDPXAPVOBNKPPD-NSCUHMNNSA-N

物化性质

• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(thymin-1'-yl)propenal 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以75%的产率得到1-(3-hydroxyprop-1-enyl)thymine
  参考文献：
  名称：

  新型细胞毒性剂：N-（3-氧代丙-1-烯基）取代的嘧啶和嘌呤的合成及生物活性。

  摘要：

  合成了胸腺嘧啶和胞嘧啶的1-（3-氧代丙-1-烯基）衍生物以及腺嘌呤和鸟嘌呤的相应9-取代衍生物（博来霉素，Fe2 +和O2降解DNA的产物）并测试了其生物学活性。胸腺嘧啶和腺嘌呤化合物对多种肿瘤细胞系具有高度细胞毒性，并抑制培养的HeLa细胞中的大分子合成。主要基于嘧啶衍生物的结构活性研究表明，最有效的抑制作用发生在丙烯基位于2'-脱氧核糖核苷的3-氮原子上时。胸苷，2'-脱氧尿苷和5-碘-2'-脱氧尿苷的3-（3-氧代丙-1-烯基）衍生物有力且选择性地抑制了胸苷向DNA中的掺入（IC50大约等于0。5 microM）与用异氧尿苷观察到的结果相当。该系列中的活性化合物易于与含有伯氨基和巯基的亲核试剂反应。这项研究的结果为开发新型细胞毒剂提供了基础。

  DOI：

  10.1021/jm00374a004
• 作为产物：
  描述：

  [(2S,3S,5R)-2-methyl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(18O)(18O)oxidanyloxyoxolan-3-yl] benzoate 生成 (E)-3-(thymin-1'-yl)propenal
  参考文献：
  名称：

  MCGALL, GLENN H.;STUBBE, JOANNE;KOZARICH, JOHN W., J. ORG. CHEM., 56,(1991) N, C. 48-55

  摘要：

  DOI：

文献信息

• Self-sacrificing acetylation observed during attempted desilylation of 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-5-O-methanesulfonyl-α-l-threo-pentofuranosyl]thymine
  作者：Hisashi Shimada、Yutaka Kubota、Hiromichi Tanaka

  DOI：10.1016/j.tetlet.2010.06.039

  日期：2010.8

  Desilylation of 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-5-O-methanesulfonyl-α-l-threo-pentofuranosyl]thymine (4) with Bu4NF/THF, when carried out at room temperature, gave four products. Among these, there were 1-[3-O-acetyl-4-benzenesulfonyl-2-deoxy-5-O-methanesulfonyl-α-l-threo-pentofuranosyl]thymine (7) and thymine. A possible reaction mechanism is proposed, which suggests the

  1-脱甲硅基[4-苯磺酰基-3- Ö - （叔丁基二甲基）-2-脱氧-5- ö甲磺酰基- α-升-苏-pentofuranosyl]胸腺嘧啶（4）配有卜4 NF / THF中，当进行在室温下取出，给出了四种产品。在这些当中，有1-〔3- ø -乙酰基-4-苯磺酰基-2-脱氧-5- ö甲磺酰基- α-升-苏-pentofuranosyl]胸腺嘧啶（7）和胸腺嘧啶。提出了一种可能的反应机理，表明了7'的3'- O-乙酰基的起源和胸腺嘧啶以及其他两种产物的结构（9a和9b）。
• Identification of the Oxidized Products Formed upon Reaction of Chromium(V) with Thymidine Nucleotides
  作者：Kent D. Sugden、Karen E. Wetterhahn

  DOI：10.1021/ja962428x

  日期：1996.1.1

  Two pathways have been observed for Cr(V)-mediated nucleotide oxidation in reactions of bis(2-ethyl-2-hydroxybutyrato)oxochromate(V) [CrO(ehba)2]- with thymidine nucleotides dTMP, dTDP, and dTTP. The extent of Cr(V)-induced nucleotide oxidation was greatest for thymidine diphosphate (dTDP), as measured by the production of thiobarbituric acid reactive species (TBARS; indicative of pathway 1) and thymine

  在双(2-乙基-2-羟基丁酸)氧铬酸盐(V) [CrO(ehba)2]-与胸苷核苷酸dTMP、dTDP和dTTP的反应中，已观察到Cr(V)介导的核苷酸氧化的两种途径。Cr(V) 诱导的核苷酸氧化的程度对于胸苷二磷酸 (dTDP) 最大，这是通过硫代巴比妥酸反应性物质 (TBARS；指示途径 1) 和胸腺嘧啶释放 (指示途径 2) 的产生来衡量的。核苷胸苷未显示反应，表明磷酸依赖性氧化。TBARS 和胸腺嘧啶的量在 6.0-6.5 的 pH 范围内最大，并且 TBARS 的形成和胸腺嘧啶的释放都与 Cr(V) EPR 信号的衰减相关。TBARS 的形成在 100% O2 中最大，但在氩气下显着减少，而胸腺嘧啶释放在氩气下最大，但仍然是在有氧条件下观察到的主要产物。Cr(V) 与 dTDP 反应的途径 1 导致乙醇酸和反式胸腺嘧啶丙烯醛以大约等摩尔浓度的形成...
• Phosphorus containing materials, their preparation and use
  申请人：——

  公开号：US20040026671A1

  公开（公告）日：2004-02-12

  There is described a co-polymerisable phosphorus containing polymer precursor which comprises: a) a polymerisable unsaturated bond; b) a oxycarbonyl or iminocarbony group; and c) a free hydroxy group or a functional group obtainable by reaction of a free hydroxy group with a suitable electrophile; and d) a terminal phosphorus and oxygen containing group located at the end of a carbon chain and comprising at least one group selected from: hydroxy phosphorus and an optionally substituted hydrocarbyl group attached to a phosphorus atom through an oxy group; where the polymer precursor: is substantially free of halo comprising species; has a molecular weight (Mn if a polymer) of from about 200 to about 5,000 daltons; and optionally, has a Hoppler viscosity measured at 25° C. of less than about 14,000 mPa.s. These polymer precursors are obtainable as the product of a reaction between an optionally substituted terminal phosphate or H-phosphonate ester and compound comprising at least one oxiranyl, preferably epoxy, ring adjacent an alkylidenylcarbonyloxy group. The polymer precursors can be copolymerised with other monomers to produce copolymers such as phosphorus containing polyurethanes which for example have use as flame retardants, anti-corrosives, pigment dispersants and/or adhesion promoters.

  描述了一种共聚磷含量聚合物前体，其包括：a）可聚合不饱和键；b）氧羰基或亚氨基羰基团；c）自由羟基或可通过与适当电子亲合剂反应获得的功能基团；以及d）位于碳链末端的含磷氧基团，包括至少一种从羟基磷和可选取代的烃基团通过氧基连接到磷原子的团；其中，聚合物前体：基本上不含卤素物种；分子量（如果是聚合物，则为Mn）为约200至约5,000道尔顿；可选地，在25℃下测得的霍普勒黏度小于约14,000mPa.s。这些聚合物前体可作为可选取代的末端磷酸盐或H-膦酸酯与至少一个邻接烷基烯基羰酰氧基团的化合物之间反应的产物获得。聚合物前体可以与其他单体共聚，以产生诸如含磷聚氨酯等共聚物，例如用作阻燃剂、防腐剂、颜料分散剂和/或粘接剂。
• Lactone/phosphite blends
  申请人：Dover Chemical Corporation

  公开号：US06224791B1

  公开（公告）日：2001-05-01

  This invention discloses synergistic blends of phosphates and lactones having a base structure of 3-phenylbenzofuran-2-one with or without other additives as stabilizers for polymers, particularly during melt processing as evidenced by changes in melt flow and in some instances, resistance to yellowing.

  本发明揭示了磷酸盐和内酯的协同混合物，其具有3-苯基苯并呋喃-2-酮的基本结构，带或不带其他添加剂作为聚合物的稳定剂，特别是在熔融加工过程中，如熔融流动性的变化和在某些情况下抵抗变黄等方面。
• Liver cell clones for artifical liver and extracorporeal liver assist device
  申请人：JMS Co., Ltd.

  公开号：EP1063289A1

  公开（公告）日：2000-12-27

  Disclosed is a blood perfusion device or apparatus that is used for bioartificial liver support. Human hepatocyte lines established from normal regenerating liver tissue and modulated in toxin-challenging conditions are provided. These functional hepatocytes exhibit extraordinarily enhanced detoxification functions, which are characterised by the elevated glutathione content and glutathione S-transferase activity. A bioreactor is constructed with the functional hepatocytes for bioartificial liver support system, which includes perfusion inlets and perfusion outlets, a containment vessel, a centrifugal pump and macroporous microcarriers where the functional hepatocytes are grown.

  所公开的是一种用于生物人工肝支持的血液灌流装置或设备。提供了从正常再生肝组织中建立并在毒素挑战条件下调节的人类肝细胞系。这些功能性肝细胞的解毒功能异常增强，其特点是谷胱甘肽含量和谷胱甘肽 S 转移酶活性升高。该系统包括灌注入口和灌注出口、密闭容器、离心泵和生长功能肝细胞的大孔微载体。