9-fluorenylmethyl N-(N-(2-dansyl)-2-aminoethyl)-carbamate | 1207722-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9-fluorenylmethyl N-(N-(2-dansyl)-2-aminoethyl)-carbamate
• 英文别名: 9H-fluoren-9-ylmethyl N-[2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]ethyl]carbamate
• CAS: 1207722-28-8
• 化学式: C₂₉H₂₉N₃O₄S
• 分子量: 515.633
• InChiKey: CKUBLFBEWCMKEF-UHFFFAOYSA-N

物化性质

• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  96.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-fluorenylmethyl N-(N-(2-dansyl)-2-aminoethyl)-carbamate 在 吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以87%的产率得到5-二甲基氨基萘-1-(n-(2-氨基乙基))磺酰胺
  参考文献：
  名称：

  Synthesis and Uptake of Fluorescence-Labeled Combi-molecules by P-Glycoprotein-Proficient and -Deficient Uterine Sarcoma Cells MES-SA and MES-SA/DX5

  摘要：

  Here, we report on the first synthesis of fluorescent-labeled epidermal growth factor receptor-DNA targeting combi-molecules, and we studied the influence of P-glycoprotein status of human sarcoma MES-SA cells on their growth inhibitory effect and Cellular uptake. The results showed that 6, bearing a longer spacer between the quinazoline ring and the dansyl group, was more stable and more cytotoxic than 4. In contrast to the latter, it induced significant levels of DNA damage in human tumor cells. Moreover, in contrast to doxorubicin, a drug known to be actively effluxed by P-gp, the more stable combi-molecule 6 induced almost identical levels of drug uptake and DNA damage in P-gp-proficient and -deficient cells. Likewise, in contrast to doxorubicin, 4 and 6 exerted equal levels of antiproliferative activity against the two cell types. The results in toto suggest that despite their size, the anti proliferative effects of 4 and 6 were independent of P-gp status of the cells.

  DOI：

  10.1021/jm9016043
• 作为产物：
  描述：

  丹酰氯 、 N-芴甲氧羰基乙二胺盐酸盐 在 potassium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 以92%的产率得到9-fluorenylmethyl N-(N-(2-dansyl)-2-aminoethyl)-carbamate
  参考文献：
  名称：

  Synthesis and Uptake of Fluorescence-Labeled Combi-molecules by P-Glycoprotein-Proficient and -Deficient Uterine Sarcoma Cells MES-SA and MES-SA/DX5

  摘要：

  Here, we report on the first synthesis of fluorescent-labeled epidermal growth factor receptor-DNA targeting combi-molecules, and we studied the influence of P-glycoprotein status of human sarcoma MES-SA cells on their growth inhibitory effect and Cellular uptake. The results showed that 6, bearing a longer spacer between the quinazoline ring and the dansyl group, was more stable and more cytotoxic than 4. In contrast to the latter, it induced significant levels of DNA damage in human tumor cells. Moreover, in contrast to doxorubicin, a drug known to be actively effluxed by P-gp, the more stable combi-molecule 6 induced almost identical levels of drug uptake and DNA damage in P-gp-proficient and -deficient cells. Likewise, in contrast to doxorubicin, 4 and 6 exerted equal levels of antiproliferative activity against the two cell types. The results in toto suggest that despite their size, the anti proliferative effects of 4 and 6 were independent of P-gp status of the cells.

  DOI：

  10.1021/jm9016043

文献信息

• Synthesis and Uptake of Fluorescence-Labeled Combi-molecules by P-Glycoprotein-Proficient and -Deficient Uterine Sarcoma Cells MES-SA and MES-SA/DX5
  作者：Anne-Laure Larroque-Lombard、Margarita Todorova、Nahid Golabi、Christopher Williams、Bertrand J. Jean-Claude

  DOI：10.1021/jm9016043

  日期：2010.3.11

  Here, we report on the first synthesis of fluorescent-labeled epidermal growth factor receptor-DNA targeting combi-molecules, and we studied the influence of P-glycoprotein status of human sarcoma MES-SA cells on their growth inhibitory effect and Cellular uptake. The results showed that 6, bearing a longer spacer between the quinazoline ring and the dansyl group, was more stable and more cytotoxic than 4. In contrast to the latter, it induced significant levels of DNA damage in human tumor cells. Moreover, in contrast to doxorubicin, a drug known to be actively effluxed by P-gp, the more stable combi-molecule 6 induced almost identical levels of drug uptake and DNA damage in P-gp-proficient and -deficient cells. Likewise, in contrast to doxorubicin, 4 and 6 exerted equal levels of antiproliferative activity against the two cell types. The results in toto suggest that despite their size, the anti proliferative effects of 4 and 6 were independent of P-gp status of the cells.