1-(3-(4-(3-(9-acridinylamine)methanethioamidopropyl)piperazin-1-yl)propyl)-3-(acridin-9-yl)thiourea | 500302-44-3

• 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: 1-(3-(4-(3-(9-acridinylamine)methanethioamidopropyl)piperazin-1-yl)propyl)-3-(acridin-9-yl)thiourea
• 英文别名: 1-Acridin-9-yl-3-[3-[4-[3-(acridin-9-ylcarbamothioylamino)propyl]piperazin-1-yl]propyl]thiourea
• CAS: 500302-44-3
• 化学式: C₃₈H₄₀N₈S₂
• 分子量: 672.921
• InChiKey: BNYVOFJYODNJAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  48
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,4-双(3-氨基丙基)哌嗪 、 9-异硫氰酸酯吖啶 以 四氢呋喃 为溶剂， 反应 6.0h， 以37%的产率得到1-(3-(4-(3-(9-acridinylamine)methanethioamidopropyl)piperazin-1-yl)propyl)-3-(acridin-9-yl)thiourea
  参考文献：
  名称：

  Synthesis of Bis-acridine Derivatives Exhibiting Anticancer and Anti-inflammatory Activity

  摘要：

  A series of bis‐acridine derivatives 3a–j and 5a–j have been synthesized by condensation of 9‐chloro‐2,4‐(un)substituted acridines (1a–e) and 9‐isothiocyanato‐2,4‐(un)substituted acridines (4a–e) with diamine 2a and 2b, respectively. These bis‐acridines were evaluated in vitro for activity against a panel of human cancer cell lines of lung (NCI H‐522), ovary (PA1), breast (T47D), colon (HCT‐15), and liver (HepG2). Several bis‐acridines were found to possess good anticancer activity against various cancer cell lines. Of these, compound 3h exhibited good anticancer activity against all cancer cell lines tested except liver (HepG2) cell line. In addition to this, these compounds were screened for anti‐inflammatory activity at a dose of 50 mg/kg p.o. Compound 3g exhibited 41% anti‐inflammatory activity, which is better than most commonly used standard drug ibuprofen, which showed 39% anti‐inflammatory (at 50 mg/kg p. o.) activity.

  DOI：

  10.1002/jhet.985

文献信息

• Synthesis of Bis-acridine Derivatives Exhibiting Anticancer and Anti-inflammatory Activity
  作者：Sham M. Sondhi、Sandeep Kumar、Reshma Rani、Ajanta Chakraborty、Partha Roy

  DOI：10.1002/jhet.985

  日期：2013.3

  A series of bis‐acridine derivatives 3a–j and 5a–j have been synthesized by condensation of 9‐chloro‐2,4‐(un)substituted acridines (1a–e) and 9‐isothiocyanato‐2,4‐(un)substituted acridines (4a–e) with diamine 2a and 2b, respectively. These bis‐acridines were evaluated in vitro for activity against a panel of human cancer cell lines of lung (NCI H‐522), ovary (PA1), breast (T47D), colon (HCT‐15), and liver (HepG2). Several bis‐acridines were found to possess good anticancer activity against various cancer cell lines. Of these, compound 3h exhibited good anticancer activity against all cancer cell lines tested except liver (HepG2) cell line. In addition to this, these compounds were screened for anti‐inflammatory activity at a dose of 50 mg/kg p.o. Compound 3g exhibited 41% anti‐inflammatory activity, which is better than most commonly used standard drug ibuprofen, which showed 39% anti‐inflammatory (at 50 mg/kg p. o.) activity.