4-phenyl-1-ethoxynaphthalene-2,3-dicarboxylic acid 2-(N,N-diethylamino)ethylimide hydrochloride | 81891-02-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 4-phenyl-1-ethoxynaphthalene-2,3-dicarboxylic acid 2-(N,N-diethylamino)ethylimide hydrochloride
• 英文别名: 2-[2-(diethylamino)ethyl]-4-ethoxy-9-phenylbenzo[f]isoindole-1,3-dione;hydrochloride
• CAS: 81891-02-3
• 化学式: C₂₆H₂₈N₂O₃*ClH
• 分子量: 452.981
• InChiKey: RHBOMYQREJWUBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.85
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-ethoxy-9-phenylbenzo[f]isoindole-1,3-dione 、 N,N-二乙基氯乙胺 以73%的产率得到
  参考文献：
  名称：

  KREPELKA, J.;VANCOUROVA, I.;HOLUBEK, J.;ROUBIK, J. VLCKOVA, D., COLLECT. CZECH. CHEM. COMMUN., 1982, 47, N 1, 304-314

  摘要：

  DOI：

文献信息

• Syntheses and antineoplastic effects of some N-substituted imides of 1-substituted 4-aryl-naphthalene-2,3-dicarboxylic acids
  作者：Jiří Křepelka、Iva Vančurová、Jiří Holubek、Jiří Roubík、Drahuše Vlčková

  DOI：10.1135/cccc19820304

  日期：——

  Condensation of anhydrides Ia-d with primary amines, 2-hydroxyethylamine or formamide gave imides III-XXII. The formation of N-(2-hydroxyethyl)imides was accompanied by replacement of the aromatic hydroxy group at position 1 by a 2-hydroxyethylamine residue (XX, XXII. Reaction of the imides XIX and XX with thionyl chloride produced the corresponding 2-chloroethyl derivatives XXIII and XXIV. Alkylation of the imide II, or its alkali salt prepared in situ, by ethyl bromacetate in a homogenous medium or by 2-(N,N-diethylamino)ethyl chloride in a biphasic medium, gave the imides XXV and XXVI, respectively. Condensation of the anhydrides Ia and/or Id with 1,2-diaminobenzene gave the respective imides XIII and XIV, and pentacyclic derivatives of 12H-benz(f)isoindole[2,1-a]benzimidazole-12-one (XXVII and XXVIII, respectively) as mixtures of positional isomers. In biological evaluation for antineoplastic efficiacy in animals with experimental tumours the imide XX proved to have the widest range of application.

  无水酐Ia-d与一级胺、2-羟乙基胺或甲酰胺发生缩合反应，生成酰亚胺III-XXII。N-(2-羟乙基)酰亚胺的形成伴随着在位置1处芳香羟基被2-羟乙基胺残基替代（XX，XXII）。酰亚胺XIX和XX与氯化硫酰反应生成相应的2-氯乙基衍生物XXIII和XXIV。酰亚胺II或其现场制备的碱盐，在均相介质中与溴乙酸乙酯或在两相介质中与2-(N,N-二乙基氨基)乙基氯化物发生烷基化反应，分别得到酰亚胺XXV和XXVI。无水酐Ia和/或Id与1,2-二氨基苯发生缩合反应，得到相应的酰亚胺XIII和XIV，以及12H-苯[f]异吲哚[2,1-a]苯并咪唑-12-酮（XXVII和XXVIII）的五环衍生物，分别为位置异构体的混合物。在对实验性肿瘤动物进行抗肿瘤效果的生物学评估中，酰亚胺XX被证明具有最广泛的应用范围。