N-(6-chloro-2-methoxy-acridin-9-yl)-N'-[3-(6-chloro-2-methoxyacridin-9-ylamino)-propyl]-propane-1,3-diamine mono(methanesulfonate) | 222051-65-2

• 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: N-(6-chloro-2-methoxy-acridin-9-yl)-N'-[3-(6-chloro-2-methoxyacridin-9-ylamino)-propyl]-propane-1,3-diamine mono(methanesulfonate)
• 英文别名: N'-(6-chloro-2-methoxyacridin-9-yl)-N-[3-[(6-chloro-2-methoxyacridin-9-yl)amino]propyl]propane-1,3-diamine;methanesulfonic acid
• CAS: 222051-65-2
• 化学式: CH₄O₃S*C₃₄H₃₃Cl₂N₅O₂
• 分子量: 710.681
• InChiKey: SARJYCRWUPERAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.81
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  甲烷磺酸 、 N-(6-chloro-2-methoxy-acridin-9-yl)-N'-[3-(6-chloro-2-methoxyacridin-9-ylamino)-propyl]-propane-1,3-diamine 以 甲醇 为溶剂， 反应 0.17h， 以85%的产率得到N-(6-chloro-2-methoxy-acridin-9-yl)-N'-[3-(6-chloro-2-methoxyacridin-9-ylamino)-propyl]-propane-1,3-diamine mono(methanesulfonate)
  参考文献：
  名称：

  Increasing antitumor activity in vivo by enhancing acridine dimer solubility with salt preparations

  摘要：

  The potent activities of many anticancer agents have been demonstrated by in vitro assays. However, their poor solubility may result in diminishing anticancer activities in vivo. Previously, we synthesized a series of bisacridine derivatives shown to be potent in cytotoxicity and DNA intercalating activity in vitro. Initially, the compound 1, (N-(6-chloro-2-methoxy-acridin-9-yl)-N'-[3-(6-chloro-2-methoxy-acridin-9-ylamino)-propyl]-propane-1,3-diamine), is insoluble in polar solvent and does not reveal antihuman COLO 205 solid-tumor activity in vivo. To enhance its solubility, three salt forms (CH(3)COOH, CH(3)SO(3)H, and CF(3)COOH) of compound 1 were synthesized and their solubility was found to be greatly improved compared with that of the free base. Among these salts, the compound 1 center dot A (tris)acetate salt has shown good solubility in H(2)O and 2.5% Cremophor (v/v) and demonstrated anti-COLO205 solid-tumor activity in vivo.

  DOI：

  10.1007/s00044-009-9213-9

文献信息

• Increasing antitumor activity in vivo by enhancing acridine dimer solubility with salt preparations
  作者：Shan-Shue Wang、Yi-Jen Lee、Shih-Chung Hsu、Chen Hsieh、Lien-Shange Chang、Shan-Yen Chou

  DOI：10.1007/s00044-009-9213-9

  日期：2010.7

  The potent activities of many anticancer agents have been demonstrated by in vitro assays. However, their poor solubility may result in diminishing anticancer activities in vivo. Previously, we synthesized a series of bisacridine derivatives shown to be potent in cytotoxicity and DNA intercalating activity in vitro. Initially, the compound 1, (N-(6-chloro-2-methoxy-acridin-9-yl)-N'-[3-(6-chloro-2-methoxy-acridin-9-ylamino)-propyl]-propane-1,3-diamine), is insoluble in polar solvent and does not reveal antihuman COLO 205 solid-tumor activity in vivo. To enhance its solubility, three salt forms (CH(3)COOH, CH(3)SO(3)H, and CF(3)COOH) of compound 1 were synthesized and their solubility was found to be greatly improved compared with that of the free base. Among these salts, the compound 1 center dot A (tris)acetate salt has shown good solubility in H(2)O and 2.5% Cremophor (v/v) and demonstrated anti-COLO205 solid-tumor activity in vivo.