(E)-3-(2-methoxy-5-pyridazinyl)acrylic acid | 173088-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-(2-methoxy-5-pyridazinyl)acrylic acid
• 英文别名: (E)-3-(3-methoxy-6-pyridazinyl)acrylic acid；(E)-3-(6-methoxypyridazin-3-yl)prop-2-enoic acid
• CAS: 173088-60-3
• 化学式: C₈H₈N₂O₃
• 分子量: 180.163
• InChiKey: ZIEFUHOGXFRWPU-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-methoxy-5-pyridazinyl)acrylic acid 在 氢溴酸 、 sodium hydride 、 1-methyl-2-chloropyridinium chloride 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.17h， 生成
  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：

  3-碘代-6-甲氧基哒嗪 在 palladium diacetate 、 氢氧化钾 、 四丁基氯化铵 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 (E)-3-(2-methoxy-5-pyridazinyl)acrylic acid
  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

• TETRAHYDROISOQUINOLINES AS ANTIMALARIAL AGENTS
  申请人：Aissaoui Hamed

  公开号：US20110281869A1

  公开（公告）日：2011-11-17

  The invention relates to novel tetrahydroisoquinoline derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including pharmaceutical compositions containing one or more of those compounds and their use as medicaments for the treatment or prevention of protozoal infections, such as especially malaria.

  这项发明涉及新型四氢异喹啉衍生物及其作为药物组合物中活性成分的用途。该发明还涉及相关方面，包括含有其中一种或多种化合物的药物组合物以及它们作为治疗或预防原虫感染的药物，尤其是疟疾的用途。
• [EN] TETRAHYDROISOQUINOLINES AS ANTIMALARIAL AGENTS<br/>[FR] TÉTRAHYDROISOQUINOLÉINES EN TANT QU'AGENTS ANTIPALUDÉENS
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2009141782A1

  公开（公告）日：2009-11-26

  The invention relates to novel tetrahydroisoquinoline derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including pharmaceutical compositions containing one or more of those compounds and their use as medicaments for the treatment

  这项发明涉及新型四氢异喹啉衍生物及其在制备药物组合物中作为活性成分的用途。该发明还涉及相关方面，包括含有其中一种或多种化合物的药物组合物以及它们作为治疗药物的用途。
• Synthesis of (6,7-dimethoxy-2-oxo-2H-chromen-4-yl)methyl 3-Arylacrylates as Water Soluble Antitumor Agents
  作者：Nguyen-Hai Nam、Ngo Anh Ngoc、Ahn Byung Zun

  DOI：10.2174/157018011794839466

  日期：2011.5.1

  Four (6,7-dimethoxy-2-oxo-2H-chromen-4-yl)methyl 3-arylacrylate (5a-d) analogues of the antitumor agent (6,7-dimethoxy-2-oxo-2H-chromen-4-yl)methyl 3-(4-methoxyphenyl)acrylate (2) were synthesized. The compounds 5a-d have one or two nitrogen atoms incorporated on the aryl moiety, and therefore could be converted into hydrochloride salts (6a-d) and these salts possess greater water solubility compared to 2. Antitumor activity evaluation of using BDF1 mice bearing 3LL tumor cells model demonstrated significant inhibitory effects of compounds 6a-d against tumor growth with inhibition rates from 37.2 to 48.2%.

  抗肿瘤剂的四种(6,7-二甲氧基-2-氧代-2H-苯并-4-基)甲基3-芳基丙烯酸酯(5a-d)类似物(6,7-二甲氧基-2-氧代-2H-苯并-4合成了3-(4-甲氧基苯基)丙烯酸(2)甲酯(2)。化合物5a-d在芳基部分上掺入了1个或2个氮原子，因此可以转化为盐酸盐(6a-d)，并且这些盐与2相比具有更大的水溶性。使用携带3LL的BDF1小鼠的抗肿瘤活性评价肿瘤细胞模型显示化合物6a-d对肿瘤生长具有显着的抑制作用，抑制率为37.2%至48.2%。
• DC-89 DERIVATIVE
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0702014A1

  公开（公告）日：1996-03-20

  A DC-89 derivative represented by general formula (1) or (2) or a pharmacologically acceptable salt thereof, having an excellent antitumor activity and useful as an antitumor drug, wherein X represents Cl or Br; R represents hydrogen or COR¹; and W represents a group of general formula (3) or (4).

  通式(1)或(2)代表的 DC-89 衍生物或其药理上可接受的盐，具有优异的抗肿瘤活性，可用作抗肿瘤药物，其中 X 代表 Cl 或 Br；R 代表氢或 COR¹；W 代表通式(3)或(4)的基团。
• US5670492A
  申请人：——

  公开号：US5670492A

  公开（公告）日：1997-09-23