(Z)-3-(4-甲氧基苄基氨基甲酰基)丙烯酸 | 146407-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (Z)-3-(4-甲氧基苄基氨基甲酰基)丙烯酸
• 英文名称: (Z)-3-(4-methoxybenzylcarbamoyl)acrylic acid
• 英文别名: (Z)-3-(4-Methoxy-benzylcarbamoyl)-acrylic acid；(Z)-4-[(4-methoxyphenyl)methylamino]-4-oxobut-2-enoic acid
• CAS: 146407-18-3
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: WPUCZNLYVFBPAH-SREVYHEPSA-N

物化性质

• 熔点：
  140-142 °C(Solv: ethyl acetate (141-78-6); methanol (67-56-1))
• 沸点：
  507.9±50.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-(4-甲氧基苄基氨基甲酰基)丙烯酸 在 三聚氯氰 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以85%的产率得到5-(4-methoxybenzylimino)-5H-furan-2-one
  参考文献：
  名称：

  Cyanuric chloride: decent dehydrating agent for an exclusive and efficient synthesis of kinetically controlled isomaleimides

  摘要：

  Starting from maleanitic and maleamic acids, a facile general approach to kinetically controlled isomaleimides has been described for the first time using cyanuric chloride as a dehydrating agent with 85-98% yields. The effect of a variety of substituents present on the aromatic ring in amine and maleic anhydride moiety, on these kinetic/thermodynamic dehydration processes of anilic acids has been also described. Under the same set of reaction conditions the phthalanilic acid gave kinetically controlled product, isoplitalimide in 91% yield, while the corresponding succinanilic acid furnished the thermodynamically more stable succinimide in high yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.027
• 作为产物：
  描述：

  4-甲氧基苄胺 、 顺丁烯二酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以72%的产率得到(Z)-3-(4-甲氧基苄基氨基甲酰基)丙烯酸
  参考文献：
  名称：

  Synthesis and bradykinin inhibitory activity of novel non-peptide compounds, and evaluation of in vivo analgesic activity

  摘要：

  A series of novel non-peptide diamide compounds was synthesized and evaluated as antibradykinin agents by utilizing guinea-pig ileum smooth muscle. Among the final compounds, (Z)-4-(4-(bis(4-fluorophenyl) methyl)piperazin-1-yl)-4-oxo-N-(4-phenylbutan-2-yl)but-2-enamide showed most favorable bradykinin inhibitory activity and demonstrated analgesic efficacies in the rat models of inflammatory and neuropathic pain. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.01.050

文献信息

• Substituted amides and hydrazides of maleic acids. Part 5. Synthesis and antiflaviviral activity of some maleic amides and hydrazides
  作者：N. V. Kolotova、V. O. Koz'minykh、É. V. Dolbilkina、E. N. Koz'minykh、V. V. Yushkov、T. A. Yushkova

  DOI：10.1007/bf02464273

  日期：1997.11

  Substituted amides and hydrazides of mateic acid are known to possess a broad spectrum of biological activity. Maleic amides showed antiinflammatory, hemostatic, and anticoagulant [3] and antiatherosclerotic [4] properties, while some maleic hydrazides exhibited bacteriostatic [5, 6], antiinflammatory [5 8], antihypoxic [9], anticonvulsive [5, 6, 10], and analgesic effects [5, I l ]. Benzylideneand

  已知丙烯酸的取代酰胺和酰肼具有广谱的生物活性。马来酸酰胺显示抗炎、止血和抗凝 [3] 和抗动脉粥样硬化 [4] 特性，而一些马来酰肼显示出抑菌 [5, 6]、抗炎 [5 8]、抗缺氧 [9]、抗惊厥 [5, 6, 10] , 镇痛作用 [5, I l ]。据报道，亚苄基和二芳基亚甲基酰肼马来酸酯具有显着的抗凝集和抗凝血酶活性 [1, 3, 11]。有数据表明取代的马来酰肼对植物的生长迟缓和刺激能力 [12, 13]。下面我们报告一些马来酸烷基和芳基酰胺 (I IV) 和马来酸苯乙酰肼 (V) 的抗黄病毒活性的研究结果。
• Cechinel Filho; Pinheiro; Nunes, Il Farmaco, 1994, vol. 49, # 10, p. 675 - 677
  作者：Cechinel Filho、Pinheiro、Nunes、Yunes、Bella Cruz、Moretto

  DOI：——

  日期：——
• [EN] NEW NON-PEPTIDE COMPOUNDS, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS NON-PEPTIDIQUES, LEUR PROCÉDÉ DE PRÉPARATION ET COMPOSITION PHARMACEUTIQUE LES CONTENANT
  申请人：PARK CHOO HEA-YOUNG

  公开号：WO2007142431A1

  公开（公告）日：2007-12-13

  [EN] The present invention relates to a novel non-peptide compound, a method for preparing the same, and a pharmaceutical composition comprising the same. The non-peptide compound of the present invention has excellent inhibitory effect on bradykinin activity, and on chronic neuropathic pain and inflammatory pain, thereby being used for preventing or treating a disease caused by bradykinin, in particular, pain.
  [FR] La présente invention concerne un nouveau composé non-peptidique, un procédé de préparation de celui-ci et une composition pharmaceutique le contenant. Le composé non-peptidique proposé par la présente invention présente un excellent effet inhibiteur sur l'activité bradykinine et sur la douleur neuropathique chronique et inflammatoire, étant ainsi utilisé pour la prévention ou le traitement d'une maladie ou une condition causée par la bradykinine, en particulier, la douleur.
• Synthesis and bradykinin inhibitory activity of novel non-peptide compounds, and evaluation of in vivo analgesic activity
  作者：Yoo Lim Kam、Hee-Kyung Rhee、Hwa-Jung Kim、Seung Keun Back、Heung Sik Na、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2010.01.050

  日期：2010.3

  A series of novel non-peptide diamide compounds was synthesized and evaluated as antibradykinin agents by utilizing guinea-pig ileum smooth muscle. Among the final compounds, (Z)-4-(4-(bis(4-fluorophenyl) methyl)piperazin-1-yl)-4-oxo-N-(4-phenylbutan-2-yl)but-2-enamide showed most favorable bradykinin inhibitory activity and demonstrated analgesic efficacies in the rat models of inflammatory and neuropathic pain. (C) 2010 Published by Elsevier Ltd.
• Cyanuric chloride: decent dehydrating agent for an exclusive and efficient synthesis of kinetically controlled isomaleimides
  作者：Kishan P. Haval、Santosh B. Mhaske、Narshinha P. Argade

  DOI：10.1016/j.tet.2005.10.027

  日期：2006.1

  Starting from maleanitic and maleamic acids, a facile general approach to kinetically controlled isomaleimides has been described for the first time using cyanuric chloride as a dehydrating agent with 85-98% yields. The effect of a variety of substituents present on the aromatic ring in amine and maleic anhydride moiety, on these kinetic/thermodynamic dehydration processes of anilic acids has been also described. Under the same set of reaction conditions the phthalanilic acid gave kinetically controlled product, isoplitalimide in 91% yield, while the corresponding succinanilic acid furnished the thermodynamically more stable succinimide in high yield. (c) 2005 Elsevier Ltd. All rights reserved.