N-(pyridin-4-yl)(diethoxyphosphoryl)acetamide | 685112-18-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(pyridin-4-yl)(diethoxyphosphoryl)acetamide
• 英文别名: Diethyl 2-oxo-2-(pyridin-4-ylamino)ethylphosphonate；2-diethoxyphosphoryl-N-pyridin-4-ylacetamide
• CAS: 685112-18-9
• 化学式: C₁₁H₁₇N₂O₄P
• 分子量: 272.241
• InChiKey: BXTRPOMPWZUUSD-UHFFFAOYSA-N

物化性质

• 沸点：
  470.7±25.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(pyridin-4-yl)(diethoxyphosphoryl)acetamide 在 sodium hydride 作用下， 以 乙二醇二甲醚 、 硝基甲烷 为溶剂， 反应 10.0h， 生成 (2E,4E,6E)-5-methyl-N-[1-[3-(7-oxofuro[3,2-g]chromen-9-yl)oxypropyl]pyridin-1-ium-4-yl]-7-(2,6,6-trimethylcyclohexen-1-yl)hepta-2,4,6-trienamide;bromide
  参考文献：
  名称：

  关于结合视黄酰胺和补骨脂素的季铵衍生物的嵌合体的光生物学特性。对培养的人类角质形成细胞的研究¶†

  摘要：

  摘要 类维生素 A 与 8-甲氧基补骨脂素 (8-MOP) 和紫外线 A (UV-A) 光联合治疗某些皮肤增生性疾病的有效性促使合成由补骨脂素构建的新“嵌合型”分子。衍生物和视黄酰胺及相关分子。嵌合体是由 8-(3-溴丙氧基)-补骨脂素与酰胺结合产生的，酰胺是通过 4-氨基-吡啶与 13E-和 13Z-视黄酸或具有只有三个双链的烯烃链的“类视黄醇”衍生物反应制备的。债券。还进行了由8-(3-溴丙氧基)-补骨脂素和肉桂酸酰胺或其4-甲氧基衍生物构建的嵌合体的合成。与 8-MOP 相比，所有嵌合体在 340-390 nm UV-A 区域都表现出强摩尔吸收率，范围为 20 000-40 000 M-1 cm-1。“类视黄醇”和类视黄醇补骨脂素嵌合体的特征是对增殖的 NCTC 2544 角质形成细胞具有显着的暗毒性（致死剂量对应于 1-5 μM 的 50% 细胞存活率 [LD50]）与肉桂酸衍生物-补骨脂素嵌合体（LD50

  DOI：

  10.1562/0031-8655(2003)078<0623:otppoc>2.0.co;2
• 作为产物：
  描述：

  二乙基磷乙酸 在 吡啶 、 氯化亚砜 作用下， 以 various solvent(s) 为溶剂， 反应 7.0h， 生成 N-(pyridin-4-yl)(diethoxyphosphoryl)acetamide
  参考文献：
  名称：

  关于结合视黄酰胺和补骨脂素的季铵衍生物的嵌合体的光生物学特性。对培养的人类角质形成细胞的研究¶†

  摘要：

  摘要 类维生素 A 与 8-甲氧基补骨脂素 (8-MOP) 和紫外线 A (UV-A) 光联合治疗某些皮肤增生性疾病的有效性促使合成由补骨脂素构建的新“嵌合型”分子。衍生物和视黄酰胺及相关分子。嵌合体是由 8-(3-溴丙氧基)-补骨脂素与酰胺结合产生的，酰胺是通过 4-氨基-吡啶与 13E-和 13Z-视黄酸或具有只有三个双链的烯烃链的“类视黄醇”衍生物反应制备的。债券。还进行了由8-(3-溴丙氧基)-补骨脂素和肉桂酸酰胺或其4-甲氧基衍生物构建的嵌合体的合成。与 8-MOP 相比，所有嵌合体在 340-390 nm UV-A 区域都表现出强摩尔吸收率，范围为 20 000-40 000 M-1 cm-1。“类视黄醇”和类视黄醇补骨脂素嵌合体的特征是对增殖的 NCTC 2544 角质形成细胞具有显着的暗毒性（致死剂量对应于 1-5 μM 的 50% 细胞存活率 [LD50]）与肉桂酸衍生物-补骨脂素嵌合体（LD50

  DOI：

  10.1562/0031-8655(2003)078<0623:otppoc>2.0.co;2

文献信息

• METHODS AND SYSTEMS FOR TREATING CELL PROLIFERATION DISORDERS WITH PSORALEN DERIVATIVES
  申请人：Toone Eric

  公开号：US20100266621A1

  公开（公告）日：2010-10-21

  Psoralen compounds of Formula (I): wherein (N + Aryl) is a member selected from the group consisting of nitrogen containing aromatic heterocycles of formulae (i)-(iii): wherein Z is a group of formula: wherein R is C 1 -C 30 hydrocarbyl, which may be linear, branched or cyclic and contains from 1 to 15 carbon-carbon double bonds, which may be conjugated or unconjugated with one another or may include an aryl ring, and may contain one or more substituents; R 1 is hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, alkene-aryl, alkene-heteroaryl, alkene-heterocyclyl, alkene-cycloalkyl, fused cycloalkylaryl, fused cycloalkylheteroaryl, fused heterocyclylaryl, fused heterocyclyheteroaryl, alkylene-fused cycloalkylaryl, alkylene-fused cycloalkylheteroaryl, alkylene-fused heterocyclylaryl, alkylene-fused heterocyclyheteroaryl; n is an integer from 1 to 8 and X is a pharmaceutically acceptable counter ion; and their use in methods for the treatment of a cell proliferation disorder in a subject, pharmaceutical compositions containing the psoralen derivatives, a kit for performing the method, and a method for causing an autovaccine effect in a subject using the method.

  公式（I）的植酸化合物：其中（N+Aryl）是从以下化学式（i）-（iii）组成的含氮芳香杂环中选择的成员：其中Z是以下化学式的一组：其中R是C1-C30烃基，可以是直链、支链或环状，并且含有1至15个碳-碳双键，这些双键可以共轭或非共轭地彼此连接，也可以包括芳香环，并且可能含有一个或多个取代基；R1是氢、芳基、杂环芳基、烷基、环烷基、杂环烷基、烯基、炔基、烯基芳基、烯基杂环芳基、烯基杂环烷基、烯基环烷基、融合环烷基芳基、融合环烷基杂环芳基、融合杂环烷基芳基、融合杂环烷基杂环芳基、烷基-融合环烷基芳基、烷基-融合环烷基杂环芳基、烷基-融合杂环烷基芳基、烷基-融合杂环烷基杂环芳基；n是1至8的整数，X是药用可接受的对离子；以及它们在治疗受体内细胞增殖紊乱的方法中的使用，含有植酸衍生物的药物组合物，用于执行该方法的工具包，以及利用该方法在受体中引起自身疫苗效应的方法。
• Synthesis and evaluation of 3-ylideneoxindole acetamides as potent anticancer agents
  作者：Chun-Tang Chiou、Wei-Chun Lee、Jiahn-Haur Liao、Jing-Jy Cheng、Lie-Chwen Lin、Chih-Yu Chen、Jen-Shin Song、Ming-Hsien Wu、Kak-Shan Shia、Wen-Tai Li

  DOI：10.1016/j.ejmech.2015.04.062

  日期：2015.6

  Indirubin, an active component in the traditional Chinese medicine formula Danggui Longhui Wan, shows promising anticancer effects. Meisoindigo is an analog derived from indirubin, which is less toxic and appears to be even more potent against cancer. In considering meisoindigo as a structural template for the development of new drugs, we designed and synthesized a series of 3-ylideneoxindole acetamides as novel anticancer agents. The acetamides were then evaluated for in vitro and in vivo anticancer activities. The 3-ylideneoxindole acetamides were found to have better anticancer activity than was indirubin-3'-oxime in several cancer cell lines and also displayed a spectrum of activity similar to that of the drug candidate roscovitine, a CDK inhibitor. Among the 3-ylideneoxindole acetamides, compound 10 showed particularly good efficacy. Cell cycle analysis further revealed that compound 10 arrested cells in the G1 phase and caused an increase in the sub-G1 population, indicating that the apoptosis pathway had been induced. In addition, exposure of cells to compound 10 led to the upregulation of the cell-cycle regulator cyclin D1, which was sustained at a high level. In contrast, the same compound induced a short-term elevation in the level of cyclin E, which was followed by a rapid decrease and the attenuation of Rb phosphorylation. Furthermore, a docking model suggests that compound 10 binds to the active site of CDK4. In testing the therapeutic potency of compound 10 on CT26-xenografted BALB/c mice, a significant reduction in tumor size comparable to that of cisplatin was found when administrated via the i.p. route. The mice presented no loss of body weight, indicating that this compound possesses low toxicity. In the future, we are planning in vivo investigations of these new active anticancer agents to better elucidate active mechanisms at the cellular level and thus benefit the development of anticancer therapies. (C) 2015 Elsevier Masson SAS. All rights reserved.
• TW2017/2223
  申请人：——

  公开号：——

  公开（公告）日：——
• US8383836B2
  申请人：——

  公开号：US8383836B2

  公开（公告）日：2013-02-26
• US8791275B2
  申请人：——

  公开号：US8791275B2

  公开（公告）日：2014-07-29