[3-amino-5-(4-{2-[bis(2-chloroethyl)amino]ethoxy}acridin-9-yl-amino)phenyl]methanol tetrahydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: [3-amino-5-(4-{2-[bis(2-chloroethyl)amino]ethoxy}acridin-9-yl-amino)phenyl]methanol tetrahydrochloride
• 英文别名: [3-Amino-5-[[4-[2-[bis(2-chloroethyl)amino]ethoxy]acridin-9-yl]amino]phenyl]methanol;hydrochloride
• 化学式: C₂₆H₂₈Cl₂N₄O₂*4ClH
• 分子量: 645.284
• InChiKey: LYEASRCWUXYYMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.6
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [3-amino-5-(4-{2-[bis(2-chloroethyl)amino]ethoxy}acridin-9-yl-amino)phenyl]methanol tetrahydrochloride 、 氯甲酸乙酯 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 以72%的产率得到3-{4-(2-[bis-(2-[bis-(2-chloroethyl)amino]ethoxy)acridin-9-ylamino]-5-hydroxymethyl)phenyl}carboxylic acid ethyl ester
  参考文献：
  名称：

  Potent Antitumor 9-Anilinoacridines and Acridines Bearing an Alkylating N-Mustard Residue on the Acridine Chromophore:  Synthesis and Biological Activity

  摘要：

  A series of 9-anilinoacridine and acridine derivatives bearing an alkylating N-mustard residue at C4 of the acridine chromophore were synthesized. The N-mustard pharmacophore was linked to the C4 of the acridine ring with an O-ethyl ( O-C-2), O-propyl ( O-C-3), or O-butyl ( O-C-4) spacer. It revealed that all newly synthesized compounds were very potent cytotoxic agents against human leukemia and various solid tumors in vitro. These agents did not exhibit cross-resistance against vinblastine-resistant ( CCRF-CEM/VBL) or taxol-resistant ( CCRF-CEM/taxol) cells. It also showed that these agents were DNA cross-linking agents rather than topoisomerase II inhibitors. Of these agents, compounds 27a and 27c were shown to have potent antitumor activity in nude mice bearing the human breast carcinoma MX-1 xenograft. The therapeutic efficacies of these two agents are comparable to that of taxol.

  DOI：

  10.1021/jm060197r
• 作为产物：
  描述：

  三(2-氯乙基)胺盐酸盐 在 N,N-二甲基甲酰胺 盐酸 、 氯化亚砜 、 potassium carbonate 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 25.67h， 生成 [3-amino-5-(4-{2-[bis(2-chloroethyl)amino]ethoxy}acridin-9-yl-amino)phenyl]methanol tetrahydrochloride
  参考文献：
  名称：

  9-anilinoacridine alkylating agents

  摘要：

  这项发明涉及9-苯胺基吖啶烷基化剂，它们的合成以及它们在治疗疾病的药物组合物中的应用。

  公开号：

  US20080176889A1

文献信息

• Potent Antitumor 9-Anilinoacridines and Acridines Bearing an Alkylating <i>N</i>-Mustard Residue on the Acridine Chromophore:  Synthesis and Biological Activity
  作者：Tsann-Long Su、Yi-Wen Lin、Ting-Chao Chou、Xiuguo Zhang、Valeriy A. Bacherikov、Ching-Huang Chen、Leroy F. Liu、Tsong-Jen Tsai

  DOI：10.1021/jm060197r

  日期：2006.6.1

  A series of 9-anilinoacridine and acridine derivatives bearing an alkylating N-mustard residue at C4 of the acridine chromophore were synthesized. The N-mustard pharmacophore was linked to the C4 of the acridine ring with an O-ethyl ( O-C-2), O-propyl ( O-C-3), or O-butyl ( O-C-4) spacer. It revealed that all newly synthesized compounds were very potent cytotoxic agents against human leukemia and various solid tumors in vitro. These agents did not exhibit cross-resistance against vinblastine-resistant ( CCRF-CEM/VBL) or taxol-resistant ( CCRF-CEM/taxol) cells. It also showed that these agents were DNA cross-linking agents rather than topoisomerase II inhibitors. Of these agents, compounds 27a and 27c were shown to have potent antitumor activity in nude mice bearing the human breast carcinoma MX-1 xenograft. The therapeutic efficacies of these two agents are comparable to that of taxol.
• 9-anilinoacridine alkylating agents
  申请人：Su Tsann-Long

  公开号：US20080176889A1

  公开（公告）日：2008-07-24

  This invention relates to 9-anilinoacridine alkylating agents, their synthesis and their use in pharmaceutical compositions for treating diseases.

  这项发明涉及9-苯胺基吖啶烷基化剂，它们的合成以及它们在治疗疾病的药物组合物中的应用。