Ethyl 5-chloro-2-hydroxyoxanilate | 79509-87-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 5-chloro-2-hydroxyoxanilate
• 英文别名: ethyl 2-(5-chloro-2-hydroxyanilino)-2-oxoacetate
• CAS: 79509-87-8
• 化学式: C₁₀H₁₀ClNO₄
• 分子量: 243.647
• InChiKey: PVEUGGBLKBHZDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  Ethyl 5-chloro-2-hydroxyoxanilate 、 N,N-二甲基-1,3-二氨基丙烷 以 乙醇 为溶剂， 反应 2.0h， 生成 N-(5-chloro-2-hydroxyphenyl)-N'-[3-(dimethylamino)propyl]oxalamide
  参考文献：
  名称：

  Bimetallic complexes constructed from asymmetrical N,N′-bis(substituted)-oxamide: Cytotoxicities, and reactivities towards DNA and protein

  摘要：

  A new asymmetrical N,N'-bis(substituted)oxamide ligand, N-(5-chloro-2-hydroxyphenyl)-N'-(3-(dimethylamino)propyl]oxamide (C13E18N3O3Cl center dot H2O, H3L) and its two binuclear complexes [Cu2L (H2O)(bpy)](ClO4)center dot CH3OH (1) and [Ni2L(bPY)(2)](ClO4) (2) [bpy = 2.2'-bipyridine] have been synthesized and characterized by X-ray single-crystal diffraction. In the crystal structure, H3L adopting a transoid conformation occurs as a neutral molecule linked with a water molecule by an intermolecular hydrogen bond. In the two complexes, the cis-L3- ligand bridges two metal ions with the corresponding separations of 5.2032(15) angstrom (1) and 5.2466(7) angstrom (2), respectively. In vitro cytotoxic activities, and the reactivities of the three compounds towards DNA and protein are investigated. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.022
• 作为产物：
  描述：

  草酰氯单乙酯 、 4-氯-2-氨基苯酚 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 Ethyl 5-chloro-2-hydroxyoxanilate
  参考文献：
  名称：

  Synthesis, structure, DNA-binding, and cytotoxic activities of N-(5-chloro-2-hydroxyphenyl)-N′-[3-(2-hydroxyethylamino)propyl]oxamide and its dicopper(II) complex

  摘要：

  A dissymmetrical N, N'-bis(substituted) oxamide, N-(5-chloro-2-hydroxyphenyl)-N'[3-(2-hydroxyethylamino) propyl] oxamide (H(3)oxpep), and its dicopper(II) complex, [Cu-2(oxpep)(phen)]ClO4 (1) (phen = 1,10-phenanthroline), were synthesized. The crystal structure of 1 was determined by single-crystal X-ray diffraction. In 1, Cu1 and Cu2 are bridged by cis-oxpep(3-) with Cu center dot center dot center dot Cu separation of 5.2007(6) angstrom. Cu1 is in a distorted squarepyramidal environment, while Cu2 has a square-planar coordination geometry. The 3-D supramolecular structure of 1 is formed through pi-pi stackings and hydrogen bonds. The DNA-binding properties and cytotoxic activities of the two compounds were investigated. The results suggest that the two compounds can interact with HS-DNA by intercalation with binding affinities following the order 1 > H(3)oxpep, which is consistent with their anticancer activities.

  DOI：

  10.1080/00958972.2011.638063

文献信息

• 2-Hydroxyoxanilic acid derivatives
  申请人：Yamanouchi Pharmaceutical Co.

  公开号：US04457872A1

  公开（公告）日：1984-07-03

  A novel 2-hydroxyoxanilic acid derivative shown by the following formula ##STR1## or a salt thereof. This compound possesses an immunoregulatory action and is useful as an antiallergic agent, an antiasthmatic, an antirheumatic, a carcinostatic agent, a therapeutic agent for autoimmune disease, and a suppressant of rejection at the tissue transplantation and skin graft.

  下列式子所示的新型2-羟基氧基苯甲酸衍生物 ##STR1## 或其盐。该化合物具有免疫调节作用，可用作抗过敏剂、抗哮喘剂、抗风湿剂、抗癌剂、自身免疫疾病治疗剂以及组织移植和皮肤移植的抑制剂。
• Synthesis, structure, DNA-binding, and cytotoxic activities of <i>N</i>-(5-chloro-2-hydroxyphenyl)-<i>N′</i>-[3-(2-hydroxyethylamino)propyl]oxamide and its dicopper(II) complex
  作者：Shi-Hao Cui、Man Jiang、Yan-Tuan Li、Zhi-Yong Wu、Xiao-Wen Li

  DOI：10.1080/00958972.2011.638063

  日期：2011.12.10

  A dissymmetrical N, N'-bis(substituted) oxamide, N-(5-chloro-2-hydroxyphenyl)-N'[3-(2-hydroxyethylamino) propyl] oxamide (H(3)oxpep), and its dicopper(II) complex, [Cu-2(oxpep)(phen)]ClO4 (1) (phen = 1,10-phenanthroline), were synthesized. The crystal structure of 1 was determined by single-crystal X-ray diffraction. In 1, Cu1 and Cu2 are bridged by cis-oxpep(3-) with Cu center dot center dot center dot Cu separation of 5.2007(6) angstrom. Cu1 is in a distorted squarepyramidal environment, while Cu2 has a square-planar coordination geometry. The 3-D supramolecular structure of 1 is formed through pi-pi stackings and hydrogen bonds. The DNA-binding properties and cytotoxic activities of the two compounds were investigated. The results suggest that the two compounds can interact with HS-DNA by intercalation with binding affinities following the order 1 > H(3)oxpep, which is consistent with their anticancer activities.
• Bimetallic complexes constructed from asymmetrical N,N′-bis(substituted)-oxamide: Cytotoxicities, and reactivities towards DNA and protein
  作者：Xiao-Wen Li、Lin Tao、Yan-Tuan Li、Zhi-Yong Wu、Cui-Wei Yan

  DOI：10.1016/j.ejmech.2012.06.022

  日期：2012.8

  A new asymmetrical N,N'-bis(substituted)oxamide ligand, N-(5-chloro-2-hydroxyphenyl)-N'-(3-(dimethylamino)propyl]oxamide (C13E18N3O3Cl center dot H2O, H3L) and its two binuclear complexes [Cu2L (H2O)(bpy)](ClO4)center dot CH3OH (1) and [Ni2L(bPY)(2)](ClO4) (2) [bpy = 2.2'-bipyridine] have been synthesized and characterized by X-ray single-crystal diffraction. In the crystal structure, H3L adopting a transoid conformation occurs as a neutral molecule linked with a water molecule by an intermolecular hydrogen bond. In the two complexes, the cis-L3- ligand bridges two metal ions with the corresponding separations of 5.2032(15) angstrom (1) and 5.2466(7) angstrom (2), respectively. In vitro cytotoxic activities, and the reactivities of the three compounds towards DNA and protein are investigated. (C) 2012 Elsevier Masson SAS. All rights reserved.