2-carboxybenzaldehyde-(4'-methoxy)-benzoylhydrazone | 346728-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-carboxybenzaldehyde-(4'-methoxy)-benzoylhydrazone
• 英文别名: 2-carboxybenzaldehyde-(4'-methoxy)benzoylhydrazone；2-[[(4-Methoxybenzoyl)hydrazinylidene]methyl]benzoic acid
• CAS: 346728-08-3
• 化学式: C₁₆H₁₄N₂O₄
• 分子量: 298.298
• InChiKey: BINZOAOSCFZENS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  88
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-carboxybenzaldehyde-(4'-methoxy)-benzoylhydrazone 、 lanthanum(III) nitrate hexahydrate 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Crystal structure, antitumor activities and DNA-binding properties of the La(III) complex with Phthalazin-1(2H)-one prepared by a novel route

  摘要：

  Phthalazin-1(2H)-one was prepared by a novel route. The La(III)-complex of phthalazin-1(2H)-one, [La(NO3)(3)center dot 4H(2)O center dot C8H7-N2O]center dot H2O, was synthesized and characterized on the basis of elemental analysis, thermal analyses (TG/DTA) and X-ray crystallography. In the complex, the coordination number of the La(III) ion is eleven. The interaction of the ligand and its complex with calf thymus DNA was investigated by spectrophotometric methods and viscosity measurements, respectively. Experimental results indicated that phthalazin-1 (2H)-one and the complex can bind to DNA by intercalation modes, but the binding affinity of La(III)complex is higher than that of the ligand. Comparative antitumor activities of La(III)-complex was investigated by HL-60 and A-549. IC50 = 2.6 x 10(-8), 3.3 x 10(-5) mg/mL are given. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.07.046
• 作为产物：
  描述：

  对甲氧基苯甲酰肼 、 邻羧基苯甲醛 以 四氢呋喃 为溶剂， 生成 2-carboxybenzaldehyde-(4'-methoxy)-benzoylhydrazone
  参考文献：
  名称：

  锡粉促进的级联缩合/烯丙基化/内酰胺化：异吲哚啉酮和吡唑并异吲哚-8-酮的合成

  摘要：

  已开发出一种有效的锡粉促进的2-甲酰基苯甲酸，酰肼和烯丙基溴的级联缩合/烯丙基化/内酰胺化反应，可在温和条件下以良好至极佳的收率合成异吲哚啉酮，而无需任何其他添加剂或催化剂。通过碘环化过程进一步操作异吲哚啉酮，得到三环四氢-8 H-吡唑并[5,1- a ] isoindol -8-one衍生物，可以将其转化为更复杂的四环四氢-4 H -azirino [1'，2' ：2,3] pyrazolo [5,1- a ] isoindol-4-ones。

  DOI：

  10.1021/acs.joc.9b00733

文献信息

• A new synthesis of phthalimidines
  作者：L. Yu. Ukhin、K. Yu. Suponitsky、L. V. Belousova、Zh. I. Orlova

  DOI：10.1007/s11172-009-0347-1

  日期：2009.12

  A new synthesis of phthalimidines is described. 3-Acyloxy-2-aryl- and 2-acylamino-3-acyloxyphthalimidines were prepared by the reaction of 3-arylaminophthalides or o-formylbenzoic acid acylhydrazones with acetic or propionic anhydrides. Their reactions with O-, N-, S-, and C-nucleophiles were studied. The structure of 2-acetyl(cyanoacetyl)amino-3-acetoxyindolin-1-one was confirmed by X-ray diffraction

  描述了邻苯二甲酰亚胺的新合成。3-酰氧基-2-芳基-和2-酰氨基-3-酰氧基邻苯二甲酰亚胺通过3-芳基氨基苯酞或邻甲酰基苯甲酸酰腙与乙酸或丙酸酐反应制备。研究了它们与 O-、N-、S-和 C-亲核试剂的反应。2-乙酰（氰基乙酰）氨基-3-乙酰氧基吲哚-1-one 的结构通过 X 射线衍射分析得到证实。
• Synthesis, Characterization and the Antioxidative Activity of 2‐Carboxybenzaldehyde‐(4′‐methoxy)benzoylhydrazone Rare Earth Complexes
  作者：Yan Wang、Zheng‐Yin Yang、Bao‐Dui Wang

  DOI：10.1081/sim-200052665

  日期：2005.4.1

  A new ligand, 2-carboxybenzaldehyde-(4'-methoxy)benzoylhydrazone, and its four rare earth complexes, RE (HL2).nH(2)O (RE = La, Dy, n = 1; RE = Sm, Eu, n = 4), have been synthesized in water and characterized on the basis of elemental analyses, molar conductivities, IR spectra, UV spectra, H-1 NMR spectra and thermal analyses. In addition, the suppression ratio for O-2(-)center dot, (a) the suppression ratio for OH center dot(b) and the inhibitory ratio for lipid peroxidation ( c) were determined with 72 spectrophotometer. The results show that IC50 (a), IC50 (b) and IC50 ( c) of the complexes are around 13.0-91.1 mu g/mL, 31.9-94.2 mu g/mL and 10.8-358.4 mu g/mL, respectively. For the ligand, IC50 (a) = 120.3 mu g/mL, IC50 (b) = 51.5 mu g/mL and IC50 (c) = 3.89 mu g/mL are given.
• Tin Powder-Promoted Cascade Condensation/Allylation/Lactamization: Synthesis of Isoindolinones and Pyrazoloisoindol-8-ones
  作者：Xiaoping Wang、Danfeng Huang、Ke-Hu Wang、Yingpeng Su、Yulai Hu

  DOI：10.1021/acs.joc.9b00733

  日期：2019.6.7

  An efficient tin powder-promoted cascade condensation/allylation/lactamization of 2-formylbenzoic acids, hydrazides, and allyl bromides was developed for the synthesis of isoindolinones in good to excellent yields under mild conditions without any other additives or catalysts. Further manipulation of isoindolinones by iodocyclization process afforded the tricyclic tetrahydro-8H-pyrazolo[5,1-a]isoindol-8-one

  已开发出一种有效的锡粉促进的2-甲酰基苯甲酸，酰肼和烯丙基溴的级联缩合/烯丙基化/内酰胺化反应，可在温和条件下以良好至极佳的收率合成异吲哚啉酮，而无需任何其他添加剂或催化剂。通过碘环化过程进一步操作异吲哚啉酮，得到三环四氢-8 H-吡唑并[5,1- a ] isoindol -8-one衍生物，可以将其转化为更复杂的四环四氢-4 H -azirino [1'，2' ：2,3] pyrazolo [5,1- a ] isoindol-4-ones。
• Crystal structure, antitumor activities and DNA-binding properties of the La(III) complex with Phthalazin-1(2H)-one prepared by a novel route
  作者：Yan Wang、Zheng-Yin Yang、Qin Wang、Qi-Kuan Cai、Kai-Bei Yu

  DOI：10.1016/j.jorganchem.2005.07.046

  日期：2005.11

  Phthalazin-1(2H)-one was prepared by a novel route. The La(III)-complex of phthalazin-1(2H)-one, [La(NO3)(3)center dot 4H(2)O center dot C8H7-N2O]center dot H2O, was synthesized and characterized on the basis of elemental analysis, thermal analyses (TG/DTA) and X-ray crystallography. In the complex, the coordination number of the La(III) ion is eleven. The interaction of the ligand and its complex with calf thymus DNA was investigated by spectrophotometric methods and viscosity measurements, respectively. Experimental results indicated that phthalazin-1 (2H)-one and the complex can bind to DNA by intercalation modes, but the binding affinity of La(III)complex is higher than that of the ligand. Comparative antitumor activities of La(III)-complex was investigated by HL-60 and A-549. IC50 = 2.6 x 10(-8), 3.3 x 10(-5) mg/mL are given. (c) 2005 Elsevier B.V. All rights reserved.