(E)-4-(butylamino)-4-oxobut-2-enoic acid | 913187-30-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-4-(butylamino)-4-oxobut-2-enoic acid
• 英文别名: trans-3-(butylcarbamoyl)acrylic acid；3-Butylcarbamoyl-acrylic acid；Fumarsaeure-monobutylamid
• CAS: 913187-30-1
• 化学式: C₈H₁₃NO₃
• mdl: MFCD01163331
• 分子量: 171.196
• InChiKey: BEWIWYDBTBVVIA-SNAWJCMRSA-N

物化性质

• 沸点：
  381.6±34.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(butylamino)-4-oxobut-2-enoic acid 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 21.0h， 生成 6-butyl-3,4,7,8-tetraphenyl-1H-pyrano[4,3-c]pyridine-1,5(6H)-dione
  参考文献：
  名称：

  Rh(III)-催化的双 C-H 功能化和单酰胺富马酸酯的 C-O/C-N 环化

  摘要：

  吡喃并[4,3 - c ]吡啶二酮是生物活性化合物和功能材料的关键骨架，通常使用昂贵的底物通过多步合成制备。这项工作表明，Rh(III) 催化的双 C(sp 2 )–H 官能化和单酰胺富马酸酯的 C–O/C–N 环化可以产生吡喃[4,3- c ]吡啶-1,5(6 H ) -单步高产率（高达 82%）的二酮。单酰胺富马酸酯和乙炔的底物结构简单、容易获得且价格低廉。添加剂AgSbF 6有效提高了产量。由于反应中COOH基团中的OH比酰胺基团中的NH更容易脱氢，该过程首先进行C-O环化，然后进行C-N环化。

  DOI：

  10.1021/acs.joc.2c02091
• 作为产物：
  描述：

  N-butylmaleamic acid 在 sodium acetate 作用下， 以 乙酸酐 为溶剂， 生成 (E)-4-(butylamino)-4-oxobut-2-enoic acid
  参考文献：
  名称：

  Maleamic and Citraconamic Acids, Methyl Esters, and Imides

  摘要：

  DOI：

  10.1021/jo01076a038

文献信息

• Design, Synthesis, and Evaluation of Aza-Peptide Michael Acceptors as Selective and Potent Inhibitors of Caspases-2, -3, -6, -7, -8, -9, and -10
  作者：Özlem Doǧan Ekici、Zhao Zhao Li、Amy J. Campbell、Karen Ellis James、Juliana L. Asgian、Jowita Mikolajczyk、Guy S. Salvesen、Rajkumar Ganesan、Stjepan Jelakovic、Markus G. Grütter、James C. Powers

  DOI：10.1021/jm0601405

  日期：2006.9.1

  novel class of inhibitors that are potent and specific for caspases-2, -3, -6, -7, -8, -9, and -10. The second-order rate constants are in the order of 10(6) M(-1) s(-1). The aza-peptide Michael acceptor inhibitor 18t (Cbz-Asp-Glu-Val-AAsp-trans-CH=CH-CON(CH(2)-1-Naphth)(2) is the most potent compound and it inhibits caspase-3 with a k(2) value of 5620000 M(-1) s(-1). The inhibitor 18t is 13700, 190

  氮杂肽迈克尔受体是一类新颖的抑制剂，对caspases-2，-3，-6，-7，-8，-9和-10具有特异性。二阶速率常数约为10（6）M（-1）s（-1）。氮杂肽迈克尔受体抑制剂18t（Cbz-Asp-Glu-Val-AAsp-trans-CH = CH-CON（CH（2）-1-Naphth）（2）是最有效的化合物，它抑制caspase-3 ak（2）值为5620000 M（-1）s（-1）。抑制剂18t对caspase-3的选择性比caspases-2，-6高13700、190、6.4、594、37500和173倍（分别为-7，-8，-9和-10），以caspase特异性序列设计的氮杂肽Michael受体具有选择性，并且与氏族CA半胱氨酸蛋白酶（如木瓜蛋白酶，组织蛋白酶B和钙蛋白酶）没有任何交叉反应性。
• Succinimide and maleimide derivatives and their use as topoisomerase II catalytic inhibitors
  申请人：Topo Target ApS

  公开号：US20030032625A1

  公开（公告）日：2003-02-13

  Maleimide and succinimide derivatives were found to be effective topoisomerase II catalytic inhibitors. Due to this property, the maleimide and succinimide derivatives were investigated for their use as cytostatic agents and thus in the treatment of cancer. The compounds of the invention can be used in combination treatments with other cytostatic agents, such as topoisomerase II poisons. The maleimide and succinimide derivatives, due to their effective topoisomerase II catalytic inhibitory activity, are also useful as extravasation agents, such as upon administration of a topoisomerase II poison.

  Maleimide和succinimide衍生物被发现是有效的拓扑异构酶II催化抑制剂。由于这种特性，对maleimide和succinimide衍生物进行了研究，以评估它们作为细胞静止剂并在癌症治疗中的应用。该发明的化合物可与其他细胞静止剂（如拓扑异构酶II毒素）联合治疗。由于其有效的拓扑异构酶II催化抑制活性，maleimide和succinimide衍生物还可用作逸出剂，例如在给予拓扑异构酶II毒素后。
• Transfer hydrogenation promoted by N-heterocyclic carbene and water
  作者：Terumasa Kato、Shin-ichi Matsuoka、Masato Suzuki

  DOI：10.1039/c5cc05117g

  日期：——

  N-Heterocyclic carbenes (NHCs) promote the transfer hydrogenation of various activated CC, CN, and NN bonds with water as the proton source.

  N-杂环卡宾（NHCs）促进了各种活化的C=C、C=N和N=N键的氢转移反应，水是质子源。
• SUCCINIMIDE AND MALEIMIDE DERIVATIVES AND THEIR USE AS TOPOISOMERASE II CATALYTIC INHIBITORS
  申请人：Jensen Buhl Peter

  公开号：US20070196360A1

  公开（公告）日：2007-08-23

  Maleimide and succinimide derivatives were found to be effective topoisomerase II catalytic inhibitors. Due to this property, the maleimide and succinimide derivatives were investigated for their use as cytostatic agents and thus in the treatment of cancer. The compounds of the invention can be used in combination treatments with other cytostatic agents, such as topoisomerase II poisons. The maleimide and succinimide derivatives, due to their effective topoisomerase II catalytic inhibitory activity, are also useful as extravasation agents, such as upon administration of a topoisomerase II poison.

  Maleimide和succinimide衍生物被发现是有效的拓扑异构酶II催化抑制剂。由于这种特性，研究了maleimide和succinimide衍生物作为细胞静止剂的用途，因此用于癌症的治疗。该发明的化合物可以与其他细胞静止剂，如拓扑异构酶II毒素，组合使用。由于其有效的拓扑异构酶II催化抑制活性，maleimide和succinimide衍生物也可用作外渗剂，例如在给予拓扑异构酶II毒素时。
• [EN] SUCCINIMIDE AND MALEIMIDE DERIVATIVES AND THEIR USE AS TOPOISOMERASE II CATALYTIC INHIBITORS<br/>[FR] DERIVES DE SUCCINIMIDE ET DE MALEIMIDE ET LEUR UTILISATION COMME INHIBITEURS CATALYTIQUES DE LA TOPOISOMERASE II
  申请人：TOPO TARGET APS

  公开号：WO2002078679A2

  公开（公告）日：2002-10-10

  Maleimide and succinimide derivatives were found to be effective topoisomerase II catalytic inhibitors. Due to this property, the maleimide and succinimide derivatives were investigated for their use as cytostatic agents and thus in the treatment of cancer. The compounds of the invention can be used in combination treatments with other cytostatic agents, such as topoisomerase II poisons. The maleimide and succinimide derivatives, due to their effective topoisomerase II catalytic inhibitory activity, are also useful as extravasation agents, such as upon administration of a topoisomerase II poison. Formula (I), wherein -J- is selected from the group consisting of (A) and (B). A compound of formula (II) for use as medicament. A compound of formula (III).