(19S)-19-ethyl-19-hydroxy-7-pyridin-3-yl-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione | 1292838-48-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: (19S)-19-ethyl-19-hydroxy-7-pyridin-3-yl-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• CAS: 1292838-48-2
• 化学式: C₂₅H₁₉N₃O₄
• 分子量: 425.444
• InChiKey: MLSRYMKFYVZQAA-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  10-羟基喜树碱 在 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (19S)-19-ethyl-19-hydroxy-7-pyridin-3-yl-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
  参考文献：
  名称：

  Synthesis and antitumor activity of 10-arylcamptothecin derivatives

  摘要：

  A series of 10-arylcamptothecin derivatives was designed and synthesized. The key step of the synthesis was achieved by employing Suzuki cross-coupling chemistry. All of the new derivatives were tested for cytotoxicity against three human tumor cell lines, BEL-7402, A549, and HL-60; most of the derivatives exhibited potent cytotoxicity. The stability study showed that compound 30 was more stable than its lead compound 10-hydroxycamptothecin under the physiological condition. Mechanistic study demonstrated that compound 30 and its hydrochloride 31 had a pharmacological profile similar with camptothecin. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.005

文献信息

• Synthesis and antitumor activity of 10-arylcamptothecin derivatives
  作者：Yu Jiao、Hongchun Liu、Meiyu Geng、Wenhu Duan

  DOI：10.1016/j.bmcl.2011.02.005

  日期：2011.4

  A series of 10-arylcamptothecin derivatives was designed and synthesized. The key step of the synthesis was achieved by employing Suzuki cross-coupling chemistry. All of the new derivatives were tested for cytotoxicity against three human tumor cell lines, BEL-7402, A549, and HL-60; most of the derivatives exhibited potent cytotoxicity. The stability study showed that compound 30 was more stable than its lead compound 10-hydroxycamptothecin under the physiological condition. Mechanistic study demonstrated that compound 30 and its hydrochloride 31 had a pharmacological profile similar with camptothecin. (C) 2011 Elsevier Ltd. All rights reserved.