(E)-methyl 3-(2-methoxy-5-pyrimidinyl)acrylate | 107166-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-methyl 3-(2-methoxy-5-pyrimidinyl)acrylate
• 英文别名: methyl (2E)-3-[2-(methyloxy)-5-pyrimidinyl]-2-propenoate；methyl (E)-3-(2-methoxy-5-pyrimidinyl)acrylate；methyl (E)-3-(2-methoxypyrimidin-5-yl)prop-2-enoate
• CAS: 107166-90-5
• 化学式: C₉H₁₀N₂O₃
• 分子量: 194.19
• InChiKey: MTPXANRAVBFGIJ-ONEGZZNKSA-N

物化性质

• 沸点：
  339.3±34.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-(2-methoxy-5-pyrimidinyl)acrylate 在 氢氧化钾 、 sodium hydride 、 1-methyl-2-chloropyridinium chloride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.67h， 生成 methyl (1R,12S)-10-[(E)-3-(2-methoxypyrimidin-5-yl)prop-2-enoyl]-4-methyl-7-oxo-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),3,8-triene-3-carboxylate
  参考文献：
  名称：

  New Water-Soluble Duocarmycin Derivatives: Synthesis and Antitumor Activity of A-Ring Pyrrole Compounds Bearing β-Heteroarylacryloyl Groups

  摘要：

  A series of A-ring pyrrole compounds of duocarmycin bearing 4'-methoxy-beta-heteroarylacryloyl groups were synthesized and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. Most of the Li 4'-methoxy-beta-heteroarylacrylates displayed in vitro anticellular activity equivalent to that of 4'-methoxycinnamates, Among the 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxy-beta-heteroarylacrylates, compound 15b having a (4-methoxy-3,5-pyrimidinyl)acryloyl as segment-B (Seg-B) showed remarkably potent in vivo antitumor activity and low peripheral blood toxicity compared with the A-ring pyrrole derivatives having the trimethoxyindole skeleton in Seg-B, which were equal to 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxycinnamates. Moreover, these 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxy-beta-heteroarylacrylates had high aqueous solubility.

  DOI：

  10.1021/jm980559y
• 作为产物：
  描述：

  2-甲氧基嘧啶 在 palladium diacetate 、 N-碘代丁二酰亚胺 、 四丁基氯化铵 、 potassium carbonate 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (E)-methyl 3-(2-methoxy-5-pyrimidinyl)acrylate
  参考文献：
  名称：

  New Water-Soluble Duocarmycin Derivatives: Synthesis and Antitumor Activity of A-Ring Pyrrole Compounds Bearing β-Heteroarylacryloyl Groups

  摘要：

  A series of A-ring pyrrole compounds of duocarmycin bearing 4'-methoxy-beta-heteroarylacryloyl groups were synthesized and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. Most of the Li 4'-methoxy-beta-heteroarylacrylates displayed in vitro anticellular activity equivalent to that of 4'-methoxycinnamates, Among the 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxy-beta-heteroarylacrylates, compound 15b having a (4-methoxy-3,5-pyrimidinyl)acryloyl as segment-B (Seg-B) showed remarkably potent in vivo antitumor activity and low peripheral blood toxicity compared with the A-ring pyrrole derivatives having the trimethoxyindole skeleton in Seg-B, which were equal to 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxycinnamates. Moreover, these 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxy-beta-heteroarylacrylates had high aqueous solubility.

  DOI：

  10.1021/jm980559y

文献信息

• [EN] PYRIMIDINONE COMPOUNDS FOR USE IN THE TREATMENT OF DISEASES OR CONDITIONS MEDIATED BY LP - PLA2<br/>[FR] COMPOSÉS DE PYRIMIDINONE UTILES DANS LE TRAITEMENT DE MALADIES OU D'ÉTATS PATHOLOGIQUES INDUITS PAR LA LP-PLA2
  申请人：GLAXO GROUP LTD

  公开号：WO2012076435A1

  公开（公告）日：2012-06-14

  The present invention relates to novel compounds that inhibit Lp-PLA2 activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases associated with the activity of Lp-PLA2, for example atherosclerosis, Alzheimer's disease, and/or diabetic macular edema (I).

  本发明涉及抑制Lp-PLA2活性的新化合物，其制备方法，含有这些化合物的组合物以及它们在治疗与Lp-PLA2活性相关的疾病中的应用，例如动脉粥样硬化、阿尔茨海默病和/或糖尿病黄斑水肿。
• DC-89 derivatives
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05670492A1

  公开（公告）日：1997-09-23

  Provided are DC-89 derivatives represented by the formula: ##STR1## wherein X represents Cl or Br, R represents hydrogen or COR.sup.1, and W represents ##STR2## and pharmaceutically acceptable salts thereof. The compounds of the present invention have excellent anti-tumor activity and are useful as anti-tumor agents.

  提供了由以下公式表示的DC-89衍生物：##STR1## 其中，X代表Cl或Br，R代表氢或COR.sup.1，W代表##STR2##以及其药学上可接受的盐。本发明化合物具有优异的抗肿瘤活性，可用作抗肿瘤剂。
• COMPOUNDS
  申请人：JIN Yun

  公开号：US20120142717A1

  公开（公告）日：2012-06-07

  The present invention relates to novel compounds that inhibit Lp-PLA 2 activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases associated with the activity of Lp-PLA 2 , for example atherosclerosis, Alzheimer's disease, and/or diabetic macular edema.

  本发明涉及一种新型化合物，其抑制Lp-PLA2活性，制备这些化合物的方法，含有它们的组合物以及它们在治疗与Lp-PLA2活性相关的疾病中的应用，例如动脉粥样硬化，阿尔茨海默病和/或糖尿病黄斑水肿。
• PYRIMIDINONE COMPOUNDS FOR USE IN THE TREATMENT OF DISEASE OR CONDITIONS MEDIATED BY LP-PLA2
  申请人：Jin Yun

  公开号：US20130252963A1

  公开（公告）日：2013-09-26

  The present invention relates to novel compounds that inhibit Lp-PLA 2 activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases associated with the activity of Lp-PLA 2 , or example atherosclerosis, Alzheimer's disease, and/or diabetic macular edema.

  本发明涉及一种新的化合物，其抑制Lp-PLA2活性，其制备过程，包含它们的组合物以及它们在治疗与Lp-PLA2活性相关的疾病中的应用，例如动脉粥样硬化，阿尔茨海默病和/或糖尿病黄斑水肿。
• Pyrimidinone compounds for use in the treatment of diseases or conditions mediated by Lp-PLA2
  申请人：Jin Yun

  公开号：US08637536B2

  公开（公告）日：2014-01-28

  The present invention relates to novel compounds that inhibit Lp-PLA2 activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases associated with the activity of Lp-PLA2, for example atherosclerosis, Alzheimer's disease, and/or diabetic macular edema.

  本发明涉及一种新型化合物，可抑制Lp-PLA2活性，其制备过程，包含它们的组合物以及它们在与Lp-PLA2活性相关的疾病治疗中的应用，例如动脉粥样硬化、阿尔茨海默病和/或糖尿病黄斑水肿。