2-(2-((2-羟基乙基)氨基)乙基)-1H-苯并[de]异喹啉-1,3(2H)-二酮 | 96807-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 2-(2-((2-羟基乙基)氨基)乙基)-1H-苯并[de]异喹啉-1,3(2H)-二酮
• 英文名称: N-<2<(2-hydroxethyl)amino>ethyl>-1,8-naphthalimide
• 英文别名: N-[2-(2-hydroxyethylamino)-ethyl]-1,8-naphthalimide；N-{2[(2-hydroxethyl)amino]ethyl}-1,8-naphthalimide；2-(2-((2-Hydroxyethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione；2-[2-(2-hydroxyethylamino)ethyl]benzo[de]isoquinoline-1,3-dione
• CAS: 96807-75-9
• 化学式: C₁₆H₁₆N₂O₃
• mdl: MFCD00181393
• 分子量: 284.315
• InChiKey: URSGUHDKQBISNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(2-((2-羟基乙基)氨基)乙基)-1H-苯并[de]异喹啉-1,3(2H)-二酮 在 硫酸 、 硝酸 作用下， 反应 1.0h， 以35.5%的产率得到3,6-dinitro-N-<2-<(2-hydroxyethyl)amino>ethyl>-1,8-naphthalimide semisulfate
  参考文献：
  名称：

  N-（氨基烷基）酰亚胺抗肿瘤剂。合成和生物活性。

  摘要：

  我们在1978年发现的1,4-二羟基-5,8-双[[[[[[[2-[（（2-羟乙基）氨基]乙基]氨基]蒽醌（DHAQ）的侧链特征与那些相似最近由其他研究者发现的3-硝基-1,8-萘甲酸N-取代的酰亚胺的研究，使我们对各种酰亚胺的N-（氨基烷基）取代的衍生物进行了系统的研究。研究领域包括：（a）环系统的选择，（b）侧链的修饰，（c）在某些选定的环系统上的取代，以及（d）上述变体的组合。初步生物学活性筛选表明，在体内和体外实验肿瘤系统中，3,6-二硝基-和3,6-二氨基-1,8-萘系的N-（二烷基氨基乙基）酰亚胺具有显着的抗白血病和嗜黑素瘤活性。 。

  DOI：

  10.1021/jm00147a016
• 作为产物：
  描述：

  1,8-萘二甲酸酐 、 羟乙基乙二胺 以 乙醇 为溶剂， 反应 6.0h， 以80%的产率得到2-(2-((2-羟基乙基)氨基)乙基)-1H-苯并[de]异喹啉-1,3(2H)-二酮
  参考文献：
  名称：

  Solvatofluorochromism of N-[2-(2-hydroxylethylamino)-ethyl]-1,8-naphthalimide in protic solvent

  摘要：

  A N-substituted naphthalimide derivative N-[2-(2-hydroxylethylamino)-ethyl]-1,8-naphthalimide (HEAN), which contains potential acceptors for hydrogen bond, was synthesized and fully characterized. The fluorescence and UV/vis behaviors of HEAN in different solvents were investigated, and its Stokes shift value and fluorescence quantum yield (Phi(f)) in each solvent were determined. A remarkable fluorescence enhancement of HEAN in protic-polar solvents but a great quenching effect in apolar, less-polar and aprotic-polar solvents were observed, suggesting the key role of the proticity of solvents. In the protic-polar solvents, the fluorescence intensity and the quantum yield of HEAN increased along with a slight red-shift of the characteristic emission wavelength (lambda(em)) with the increase of solvent polarity. Maximum Or value of 0.453 for HEAN was found in water solvent with a Stokes shift of 4636 cm(-1). The inhibition of the photoinduced electron transfer (PET) by the intermolecular hydrogen-bonding interactions between protic solvents and HEAN was proposed to be responsible for its strong fluorescence enhancement. Such solvatofluorochromic property of HEAN may make it as a prospective fluorescent chemosensor to distinguish a protic solvent from aprotic solvents. (c) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2008.07.017

文献信息

• ZEE-CHENG, R. K. Y.;CHENG, C. C., J. MED. CHEM., 1985, 28, N 9, 1216-1222
  作者：ZEE-CHENG, R. K. Y.、CHENG, C. C.

  DOI：——

  日期：——
• N-(Aminoalkyl)imide antineoplastic agents. Synthesis and biological activity
  作者：Robert K. Y. Zee-Cheng、C. C. Cheng

  DOI：10.1021/jm00147a016

  日期：1985.9

  substitution on certain chosen ring systems, and (d) combinations of the aforementioned variants. Preliminary biological activity screening indicated that N-(dialkylaminoethyl)imides of the 3,6-dinitro- and 3,6-diamino-1,8-naphthalic acid system possessed prominent antileukemia and antimelanoma activity in both in vitro and in vivo experimental tumor systems.

  我们在1978年发现的1,4-二羟基-5,8-双[[[[[[[2-[（（2-羟乙基）氨基]乙基]氨基]蒽醌（DHAQ）的侧链特征与那些相似最近由其他研究者发现的3-硝基-1,8-萘甲酸N-取代的酰亚胺的研究，使我们对各种酰亚胺的N-（氨基烷基）取代的衍生物进行了系统的研究。研究领域包括：（a）环系统的选择，（b）侧链的修饰，（c）在某些选定的环系统上的取代，以及（d）上述变体的组合。初步生物学活性筛选表明，在体内和体外实验肿瘤系统中，3,6-二硝基-和3,6-二氨基-1,8-萘系的N-（二烷基氨基乙基）酰亚胺具有显着的抗白血病和嗜黑素瘤活性。 。
• Solvatofluorochromism of N-[2-(2-hydroxylethylamino)-ethyl]-1,8-naphthalimide in protic solvent
  作者：Jingwen Chen、Ruiren Tang、Zuowen Luo、Chunsheng Yang

  DOI：10.1016/j.molstruc.2008.07.017

  日期：2009.1

  A N-substituted naphthalimide derivative N-[2-(2-hydroxylethylamino)-ethyl]-1,8-naphthalimide (HEAN), which contains potential acceptors for hydrogen bond, was synthesized and fully characterized. The fluorescence and UV/vis behaviors of HEAN in different solvents were investigated, and its Stokes shift value and fluorescence quantum yield (Phi(f)) in each solvent were determined. A remarkable fluorescence enhancement of HEAN in protic-polar solvents but a great quenching effect in apolar, less-polar and aprotic-polar solvents were observed, suggesting the key role of the proticity of solvents. In the protic-polar solvents, the fluorescence intensity and the quantum yield of HEAN increased along with a slight red-shift of the characteristic emission wavelength (lambda(em)) with the increase of solvent polarity. Maximum Or value of 0.453 for HEAN was found in water solvent with a Stokes shift of 4636 cm(-1). The inhibition of the photoinduced electron transfer (PET) by the intermolecular hydrogen-bonding interactions between protic solvents and HEAN was proposed to be responsible for its strong fluorescence enhancement. Such solvatofluorochromic property of HEAN may make it as a prospective fluorescent chemosensor to distinguish a protic solvent from aprotic solvents. (c) 2008 Elsevier B.V. All rights reserved.