4-(4-hydroxyphthalazin-1-yl)benzoic acid | 152567-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(4-hydroxyphthalazin-1-yl)benzoic acid
• CAS: 152567-94-7
• 化学式: C₁₅H₁₀N₂O₃
• mdl: MFCD02053143
• 分子量: 266.256
• InChiKey: GPMAGXCWKPUWCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-hydroxyphthalazin-1-yl)benzoic acid 在 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 4-[3-(2-Imidazol-1-yl-ethyl)-4-oxo-3,4-dihydro-phthalazin-1-yl]-benzoic acid ethyl ester
  参考文献：
  名称：

  Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones

  摘要：

  A number of 4-substituted 2-[omega-(1-imidazolyl)allryl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane Az synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.

  DOI：

  10.1021/jm00077a008
• 作为产物：
  描述：

  2-(4-甲基苯甲酰)苯甲酸 在 potassium permanganate 、 肼 作用下， 以 甲醇 、 水 为溶剂， 生成 4-(4-hydroxyphthalazin-1-yl)benzoic acid
  参考文献：
  名称：

  聚（ADP-核糖）聚合酶抑制剂缀合的铂（IV）抗癌复合物的合成，细胞毒性和机理研究。

  摘要：

  已经进行了许多使用铂类药物和PARP-1抑制剂（PARPi）组合的临床试验，希望这种组合将导致增强的抗肿瘤治疗效果。本文中，我们获得了七个具有结构多样性的潜在PARPi，然后将它们与基于顺铂的铂（IV）配合物缀合。合成的PARPi配体和PARPi-Pt缀合物[PARPi-Pt（IV）]均显示出对PARP-1催化活性的抑制作用。PARPi-Pt（IV）缀合物在一组人类癌细胞系中具有细胞毒性，而领先的缀合物具有克服顺铂耐药性的能力。机理研究表明，代表性的PARPi-Pt（IV）缀合物有效进入细胞，与基因组DNA结合，干扰细胞周期分布，并在顺铂敏感和耐药细胞中诱导凋亡性细胞死亡。我们的研究提供了一种策略，可通过使用同时破坏DNA和抑制PARP的小分子抗癌复合物来改善基于铂（IV）的抗癌复合物的细胞毒性并克服顺铂耐药性。

  DOI：

  10.1021/acs.inorgchem.9b02839

文献信息

• EP2547735B1
  申请人：——

  公开号：EP2547735B1

  公开（公告）日：2016-03-16
• ANTI-CORROSION AGENTS FOR TRANSPARENT CONDUCTIVE FILM
  申请人：Zou Chaofeng

  公开号：US20130004765A1

  公开（公告）日：2013-01-03

  1,2-Diazine compounds have been found to provide anti-corrosion properties when incorporated into silver nanowire containing films. The 1,2-diazine compounds have the general structure (I) or (II).
• [EN] ANTI-CORROSION AGENTS FOR TRANSPARENT CONDUCTIVE FILM<br/>[FR] AGENTS ANTICORROSION POUR FILM CONDUCTEUR TRANSPARENT
  申请人：CARESTREAM HEALTH INC

  公开号：WO2011115603A1

  公开（公告）日：2011-09-22

  1,2-Diazine compounds have been found to provide anti-corrosion properties when incorporated into silver nanowire containing films. The 1,2-diazine compounds have the general structure (I) or (II).
• Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones
  作者：Masahisa Yamaguchi、Kenshi Kamei、Takaki Koga、Michitaka Akima、Toshio Kuroki、Nobuhiro Ohi

  DOI：10.1021/jm00077a008

  日期：1993.12

  A number of 4-substituted 2-[omega-(1-imidazolyl)allryl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane Az synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.
• Synthesis, Cytotoxicity, and Mechanistic Investigation of Platinum(IV) Anticancer Complexes Conjugated with Poly(ADP-ribose) Polymerase Inhibitors
  作者：Zoufeng Xu、Cai Li、Qiyuan Zhou、Zhiqin Deng、Zixuan Tong、Man-Kit Tse、Guangyu Zhu

  DOI：10.1021/acs.inorgchem.9b02839

  日期：2019.12.2

  combinations of platinum drugs and PARP-1 inhibitors (PARPi) have been carried out, with the hope that such combinations will lead to enhanced therapeutic outcomes against tumors. Herein, we obtained seven potential PARPi with structural diversity and then conjugated them with cisplatin-based platinum(IV) complexes. Both the synthesized PARPi ligands and PARPi-Pt conjugates [PARPi-Pt(IV)] show inhibitory

  已经进行了许多使用铂类药物和PARP-1抑制剂（PARPi）组合的临床试验，希望这种组合将导致增强的抗肿瘤治疗效果。本文中，我们获得了七个具有结构多样性的潜在PARPi，然后将它们与基于顺铂的铂（IV）配合物缀合。合成的PARPi配体和PARPi-Pt缀合物[PARPi-Pt（IV）]均显示出对PARP-1催化活性的抑制作用。PARPi-Pt（IV）缀合物在一组人类癌细胞系中具有细胞毒性，而领先的缀合物具有克服顺铂耐药性的能力。机理研究表明，代表性的PARPi-Pt（IV）缀合物有效进入细胞，与基因组DNA结合，干扰细胞周期分布，并在顺铂敏感和耐药细胞中诱导凋亡性细胞死亡。我们的研究提供了一种策略，可通过使用同时破坏DNA和抑制PARP的小分子抗癌复合物来改善基于铂（IV）的抗癌复合物的细胞毒性并克服顺铂耐药性。