(E)-2-[1-oxo-3-phenyl-2-propenyl]-2-hydroxy-benzoic acid hydrazide | 913258-88-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-[1-oxo-3-phenyl-2-propenyl]-2-hydroxy-benzoic acid hydrazide
• 英文别名: 3-phenyl-trans-2-propenoylsalicylhydrazide；N-Salicyloyl-N'-cinnamoylhydrazine；2-hydroxy-N'-[(E)-3-phenylprop-2-enoyl]benzohydrazide
• CAS: 913258-88-5
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: LODHFNUFVRVKTH-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-[1-oxo-3-phenyl-2-propenyl]-2-hydroxy-benzoic acid hydrazide 、 水 、 manganese(II) acetate 、 二甲基亚砜 以 乙醇 、 二甲基亚砜 为溶剂， 生成 [Mn20(3-phenyl-trans-2-propenoylsalicylhydrazide(-3H))20(dimethyl sulfoxide)18(H2O)2]
  参考文献：
  名称：

  Steric Control of a Bridging Ligand for High-Nuclearity Metallamacrocycle Formation:  A Highly Puckered 60-Membered Icosanuclear Metalladiazamacrocycle

  摘要：

  A novel S-4-symmetric icosanuclear manganese metalladiazamacrocycle was synthesized using a pentadentate ligand, N-3-phenyl-trans-2- propenoylsalicylhydrazide (H3L), that has a rigid and bulky terminal N-acyl group. A 20 cyclic repeat of an -(Mn-N-N)-linkage resulted in a highly puckered diaza-bridged 60-membered icosanuclear metallamacrocycle. The steric interaction between the ligands in the cyclic system leads to five consecutive Mn-III centers in a chemically different -(MnAMnBMnCMnDMnE)- environment, with the chiralities of the metal centers being in a rather complicated -(Lambda Lambda Delta Lambda Lambda)(Delta Delta Lambda Delta Delta)- sequence.

  DOI：

  10.1021/ic060646d
• 作为产物：
  描述：

  肉桂酸 、 水杨酰肼 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.08h， 以86%的产率得到(E)-2-[1-oxo-3-phenyl-2-propenyl]-2-hydroxy-benzoic acid hydrazide
  参考文献：
  名称：

  Synthesis, biological evaluation, and structure–activity relationship study of novel cytotoxic aza-caffeic acid derivatives

  摘要：

  Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl) piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl) prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC(50) values of 0.2, 2.0, 1.7, and 1.1 mu M, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.016

文献信息

• US4052362A
  申请人：——

  公开号：US4052362A

  公开（公告）日：1977-10-04
• Synthesis, biological evaluation, and structure–activity relationship study of novel cytotoxic aza-caffeic acid derivatives
  作者：Hongbin Zou、Hao Wu、Xiangnan Zhang、Yu Zhao、Joachim Stöckigt、Yijia Lou、Yongping Yu

  DOI：10.1016/j.bmc.2010.07.016

  日期：2010.9

  Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl) piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl) prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC(50) values of 0.2, 2.0, 1.7, and 1.1 mu M, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner. (C) 2010 Elsevier Ltd. All rights reserved.
• Steric Control of a Bridging Ligand for High-Nuclearity Metallamacrocycle Formation:  A Highly Puckered 60-Membered Icosanuclear Metalladiazamacrocycle
  作者：Dohyun Moon、Kyungjae Lee、Rohith P. John、Ghyung Hwa Kim、Byoung Jin Suh、Myoung Soo Lah

  DOI：10.1021/ic060646d

  日期：2006.10.1

  A novel S-4-symmetric icosanuclear manganese metalladiazamacrocycle was synthesized using a pentadentate ligand, N-3-phenyl-trans-2- propenoylsalicylhydrazide (H3L), that has a rigid and bulky terminal N-acyl group. A 20 cyclic repeat of an -(Mn-N-N)-linkage resulted in a highly puckered diaza-bridged 60-membered icosanuclear metallamacrocycle. The steric interaction between the ligands in the cyclic system leads to five consecutive Mn-III centers in a chemically different -(MnAMnBMnCMnDMnE)- environment, with the chiralities of the metal centers being in a rather complicated -(Lambda Lambda Delta Lambda Lambda)(Delta Delta Lambda Delta Delta)- sequence.