2-{(2-hydroxyethyl)-[4-(3-nitrophenoxy)butyl]amino}ethanol | 858136-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-{(2-hydroxyethyl)-[4-(3-nitrophenoxy)butyl]amino}ethanol
• 英文别名: 2-[2-hydroxyethyl-[4-(3-nitrophenoxy)butyl]amino]ethanol
• CAS: 858136-18-2
• 化学式: C₁₄H₂₂N₂O₅
• 分子量: 298.339
• InChiKey: GKUHUVDOPWCFFH-UHFFFAOYSA-N

物化性质

• 沸点：
  486.3±35.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-{(2-hydroxyethyl)-[4-(3-nitrophenoxy)butyl]amino}ethanol 在 盐酸 、 甲基磺酰氯 、 三乙胺 、 tin(ll) chloride 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 56.5h， 生成 acridin-9-yl-(3-{4-[bis(2-chloroethyl)amino]butoxy}phenyl)amine dihydrochloride
  参考文献：
  名称：

  Potent antitumor 9-anilinoacridines bearing an alkylating N-mustard residue on the anilino ring: synthesis and biological activity

  摘要：

  A series of N-mustard derivatives of 9-anilinoacridine was synthesized for antitumor and structure-activity relationship studies. The alkylating N-mustard residue was linked to the C-3' or C-4' position of the anilino ring with an O-ethylene (O-C-2) O-butylene (O-C-4), and methylene (C-1) spacer. All of the new N-mustard derivatives exhibited significant cytotoxicity in inhibiting human lymphoblastic leukemic cells (CCRF-CEM) in culture. Of these agents, (3-(acridin-9-ylamino)-5-{2-[bis(2-chloroethyl)amino]ethoxy}phenyl)methanol (10) was subjected to antitumor studies, resulting in an approximately 100-fold more potent effect than its parent analogue 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA) in inhibiting the growth of human lymphoblastic leukemic cells (CCRF-CEM) in vitro. This agent did not exhibit cross-resistance against vinblastine-resistant (CCRF-CEM/VBL) or Taxol-resistant (CCRF-CEM/Taxol) cells. Remarkably, the therapeutic effect of 10 at a dose as low as one tenth of the Taxol therapeutic dose [i.e., 1-2 mg/kg (Q3D x 7) or 3 mg/kg (Q4D x 5); intravenous injection] on nude mice bearing human breast carcinoma MX-1 xenografts resulted in complete tumor remission in two out of three mice. Furthermore, 10 yielded xenograft tumor suppression of 81-96% using human T-cell acute lymphoblastic leukemia CCRF-CEM, colon carcinoma HCT-116, and ovarian adenocarcinoma SK-OV-3 tumor models. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.057
• 作为产物：
  描述：

  间硝基苯酚 生成 2-{(2-hydroxyethyl)-[4-(3-nitrophenoxy)butyl]amino}ethanol
  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