tert-butyl (3-((tert-butoxycarbonyl)amino)propyl)(3-(((4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)amino)propyl)carbamate | 1609137-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: tert-butyl (3-((tert-butoxycarbonyl)amino)propyl)(3-(((4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)amino)propyl)carbamate
• CAS: 1609137-19-0
• 化学式: C₃₄H₄₇N₃O₉
• 分子量: 641.762
• InChiKey: DXWGFVBLLVOTPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  141.73
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3-((tert-butoxycarbonyl)amino)propyl)(3-(((4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)amino)propyl)carbamate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 N¹,N³-di-(t-butyloxycarbonyl)-N¹-(3-(1,3,8-tri-O-methylemodin-6-ylmethylamino)propyl)propane-1,3-diamine trihydrochloride
  参考文献：
  名称：

  Potent P-glycoprotein inhibition of emodin derivative: synthesis and biological evaluation

  摘要：

  A new series of emodin derivatives was prepared and evaluated for their in vitro antiproliferative activity. Preliminary results revealed that these derivatives exhibited weak or negligible cytotoxicity at 10 mu M against various cancer cell lines (i.e., K562, HepG2, and HCT116 cell lines) as well as normal hepatic cells (QSG7701). Interestingly, the evaluation for P-glycoprotein (P-gp) modulation indicated that they possessed potent P-gp inhibitory activity. Among them, the effect of compound 6 on P-gp inhibition was even greater than that of Verapamil, the known P-gp modulator. Therefore, the natural emodin scaffold could be employed as safe and effective modulator of P-gp mediated drug resistance in cancer chemotherapy.

  DOI：

  10.1007/s00044-013-0805-z
• 作为产物：
  描述：

  (3-tert-BOCamino-propyl)-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamic acid tert-butyl ester 在 potassium carbonate 、 肼 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 16.0h， 生成 tert-butyl (3-((tert-butoxycarbonyl)amino)propyl)(3-(((4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)amino)propyl)carbamate
  参考文献：
  名称：

  Potent P-glycoprotein inhibition of emodin derivative: synthesis and biological evaluation

  摘要：

  A new series of emodin derivatives was prepared and evaluated for their in vitro antiproliferative activity. Preliminary results revealed that these derivatives exhibited weak or negligible cytotoxicity at 10 mu M against various cancer cell lines (i.e., K562, HepG2, and HCT116 cell lines) as well as normal hepatic cells (QSG7701). Interestingly, the evaluation for P-glycoprotein (P-gp) modulation indicated that they possessed potent P-gp inhibitory activity. Among them, the effect of compound 6 on P-gp inhibition was even greater than that of Verapamil, the known P-gp modulator. Therefore, the natural emodin scaffold could be employed as safe and effective modulator of P-gp mediated drug resistance in cancer chemotherapy.

  DOI：

  10.1007/s00044-013-0805-z