9-(4-{2-[bis(2-chloroethyl)amino]ethoxy}phenylamino)-5-methylacridin-4-carboxylic acid (2-dimethylaminoethyl)amide

• 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: 9-(4-{2-[bis(2-chloroethyl)amino]ethoxy}phenylamino)-5-methylacridin-4-carboxylic acid (2-dimethylaminoethyl)amide
• 英文别名: 9-[4-[2-[bis(2-chloroethyl)amino]ethoxy]anilino]-N-[2-(dimethylamino)ethyl]-5-methylacridine-4-carboxamide
• 化学式: C₃₁H₃₇Cl₂N₅O₂
• 分子量: 582.573
• InChiKey: NAPDSKSTWQOVQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  69.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  三(2-氯乙基)胺盐酸盐 在 盐酸 、 potassium fluoride 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 乙醇 、 氯仿 、 丙酮 为溶剂， 生成 9-(4-{2-[bis(2-chloroethyl)amino]ethoxy}phenylamino)-5-methylacridin-4-carboxylic acid (2-dimethylaminoethyl)amide
  参考文献：
  名称：

  Potent antitumor N-mustard derivatives of 9-anilinoacridine, synthesis and antitumor evaluation

  摘要：

  A series of 9-anilinoacridine N-mustard derivatives, in which the alkylating N-mustard residue was linked to the C-3' or C-4' position of the anilino ring with an O-ethylene spacer, was synthesized and evaluated for cytotoxicity against human lymphoblastic leukemic cells (CCRF-CEM) in culture. The results showed that all of the new compounds exhibited potent cytotoxicity with IC50 values ranging from 0.002 to 0.7 muM, which were as potent or significantly more potent than 3-(9-acridinylamino)-5-hydroxy-methylaniline (AHMA). Compound 9 did not exhibit cross-resistance against both vinblastine-resistant (CCRF-CEM/VBL) and taxol-resistant (CCRF-CEM/taxol) cells. Additionally, compound 9 demonstrated potent antitumor effect in nude mice bearing human breast carcinoma MX-1 xenografts, resulting in complete tumor remission in two out of three mice at the maximal dose of 1-2 mg/kg (Q3Dx7) or 3 mg/kg (Q4Dx5) via intravenous injection. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.080

文献信息

• 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。
• Potent antitumor N-mustard derivatives of 9-anilinoacridine, synthesis and antitumor evaluation
  作者：Valeriy A. Bacherikov、Ting-Chao Chou、Hua-Jin Dong、Ching-Huang Chen、Yi-Wen Lin、Tsong-Jen Tsai、Tsann-Long Su

  DOI：10.1016/j.bmcl.2004.06.080

  日期：2004.9

  A series of 9-anilinoacridine N-mustard derivatives, in which the alkylating N-mustard residue was linked to the C-3' or C-4' position of the anilino ring with an O-ethylene spacer, was synthesized and evaluated for cytotoxicity against human lymphoblastic leukemic cells (CCRF-CEM) in culture. The results showed that all of the new compounds exhibited potent cytotoxicity with IC50 values ranging from 0.002 to 0.7 muM, which were as potent or significantly more potent than 3-(9-acridinylamino)-5-hydroxy-methylaniline (AHMA). Compound 9 did not exhibit cross-resistance against both vinblastine-resistant (CCRF-CEM/VBL) and taxol-resistant (CCRF-CEM/taxol) cells. Additionally, compound 9 demonstrated potent antitumor effect in nude mice bearing human breast carcinoma MX-1 xenografts, resulting in complete tumor remission in two out of three mice at the maximal dose of 1-2 mg/kg (Q3Dx7) or 3 mg/kg (Q4Dx5) via intravenous injection. (C) 2004 Elsevier Ltd. All rights reserved.