(E)-3-(2-methoxy-5-pyrimidinyl)acrylic acid | 173088-57-8

• 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-pyrimidinyl)acrylic acid
• 英文别名: 3-(2-Methoxypyrimidin-5-yl)prop-2-enoic acid；(E)-3-(2-methoxypyrimidin-5-yl)prop-2-enoic acid
• CAS: 173088-57-8
• 化学式: C₈H₈N₂O₃
• 分子量: 180.163
• InChiKey: BCYFMZHVHYJSTO-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 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-pyrimidinyl)acrylic acid 在 sodium hydride 、 1-methyl-2-chloropyridinium chloride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.67h， 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 、 氢氧化钾 、 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 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (E)-3-(2-methoxy-5-pyrimidinyl)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。
• Pyrimidinone compounds
  申请人：SmithKline Beecham p.l.c.

  公开号：US20040167142A1

  公开（公告）日：2004-08-26

  Pyrimidinone compounds of formula (I) are inhibitors of the enzyme Lp-PLA 2 and of use in therapy, in particular for treating atherosclerosis. 1

  式（I）的嘧啶酮化合物是Lp-PLA2酶的抑制剂，可用于治疗，特别是用于治疗动脉粥样硬化。
• [EN] INDAZOLE DERIVATIVES AS αV INTEGRIN ANTAGONISTS<br/>[FR] DÉRIVÉS D'INDAZOLE EN TANT QU'ANTAGONISTES DE L'INTÉGRINE αV
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018089357A1

  公开（公告）日：2018-05-17

  The present invention provides compounds of Formula (Ia) or (Ib): or stereoisomers, tautomers, or pharmaceutically acceptable salts or solvates thereof, wherein all the variables are as defined herein. These compounds are antagonists to αV- containing integrins. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating a disease, disorder, or condition associated with dysregulation of αV-containing integrins, such as pathological fibrosis, transplant rejection, cancer, osteoporosis, and inflammatory disorders, by using the compounds and pharmaceutical compositions.

  本发明提供了式（Ia）或（Ib）的化合物：或其立体异构体、互变异构体或药学上可接受的盐或溶剂，其中所有变量如本文所定义。这些化合物是αV-含有整合素的拮抗剂。本发明还涉及包括这些化合物的药物组合物以及使用这些化合物和药物组合物治疗与αV-含有整合素失调相关的疾病、紊乱或状况的方法，如病理性纤维化、移植排斥、癌症、骨质疏松症和炎症性疾病。
• 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。