(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[((S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yloxycarbonyl)-methyl-amino]-4-nitro-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester | 549520-67-4

• 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: (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[((S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yloxycarbonyl)-methyl-amino]-4-nitro-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 549520-67-4
• 化学式: C₄₃H₄₂N₄O₁₈
• 分子量: 902.822
• InChiKey: VXLQOFWZBYDCCC-BLGASMIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  65.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  277.76
• 氢给体数：
  1.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[((S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yloxycarbonyl)-methyl-amino]-4-nitro-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 在 甲醇 、 sodium hydroxide 、 sodium methylate 作用下， 生成 (2S,3S,4S,5R,6S)-6-[2-[[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl]oxycarbonyl-methylamino]-4-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Cancer chemotherapy: A SN-38 (7-Ethyl-10-hydroxycamptothecin) glucuronide prodrug for treatment by a PMT (Prodrug monoTherapy) strategy

  摘要：

  A glucuronide-based prodrug of SN-38 (7-etbyl-10-hydroxycamptothecin) has been synthesized for use in a Prodrug MonoTherapy Strategy (PMT). Since this prodrug is significantly less cytotoxic than SN-38 itself and efficiently releases the drug in vitro in the presence of beta-D-glucuronidase, it can be considered as an appropriate candidate for cancer treatment by a PMT strategy. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01080-6
• 作为产物：
  描述：

  7-乙基-10-羟基喜树碱 、 (2S,3R,4S,5S,6S)-2-(2-((chlorocarbonyl)(methyl)amino)-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[((S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yloxycarbonyl)-methyl-amino]-4-nitro-phenoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Cancer chemotherapy: A SN-38 (7-Ethyl-10-hydroxycamptothecin) glucuronide prodrug for treatment by a PMT (Prodrug monoTherapy) strategy

  摘要：

  A glucuronide-based prodrug of SN-38 (7-etbyl-10-hydroxycamptothecin) has been synthesized for use in a Prodrug MonoTherapy Strategy (PMT). Since this prodrug is significantly less cytotoxic than SN-38 itself and efficiently releases the drug in vitro in the presence of beta-D-glucuronidase, it can be considered as an appropriate candidate for cancer treatment by a PMT strategy. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01080-6