methyl 2-[(19S)-19-ethyl-19-hydroxy-8-nitro-14,18-dioxo-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)-heptaen-12-yl]acetate | 200616-01-9

• 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: methyl 2-[(19S)-19-ethyl-19-hydroxy-8-nitro-14,18-dioxo-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)-heptaen-12-yl]acetate
• CAS: 200616-01-9
• 化学式: C₂₃H₁₉N₃O₈
• 分子量: 465.419
• InChiKey: JTOFEPVVEWCHID-VXLWULRPSA-N

物化性质

• 沸点：
  837.4±65.0 °C(predicted)
• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2-[(19S)-19-ethyl-19-hydroxy-8-nitro-14,18-dioxo-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)-heptaen-12-yl]acetate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以75%的产率得到2-[(19S)-19-ethyl-19-hydroxy-8-nitro-14,18-dioxo-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)-heptaen-12-yl]acetic acid
  参考文献：
  名称：

  Novel C-ring analogues of 20(S)-camptothecin-part-2: Synthesis and cytotoxicity of 5-C-substituted 20(S)-camptothecin analogues

  摘要：

  A series of 5-C-substituted 20(S)-camptothecin analogues were synthesised and evaluated their in vitro anti-cancer activity. Several of these analogues have showed excellent activity against human tumor cell lines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00268-1
• 作为产物：
  描述：

  鲁比替康 在 吡啶 、 盐酸 、 硫酸 、 三氯化铁 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 methyl 2-[(19S)-19-ethyl-19-hydroxy-8-nitro-14,18-dioxo-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)-heptaen-12-yl]acetate
  参考文献：
  名称：

  Novel C-ring analogues of 20(S)-camptothecin-part-2: Synthesis and cytotoxicity of 5-C-substituted 20(S)-camptothecin analogues

  摘要：

  A series of 5-C-substituted 20(S)-camptothecin analogues were synthesised and evaluated their in vitro anti-cancer activity. Several of these analogues have showed excellent activity against human tumor cell lines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00268-1

文献信息

• NOVEL WATER-SOLUBLE ANALOGUES OF 20(S)-CAMPTOTHECIN
  申请人：DR. REDDY'S RESEARCH FOUNDATION

  公开号：EP0906316A1

  公开（公告）日：1999-04-07
• US6214836B1
  申请人：——

  公开号：US6214836B1

  公开（公告）日：2001-04-10
• [EN] NOVEL WATER-SOLUBLE ANALOGUES OF 20(S)-CAMPTOTHECIN<br/>[FR] NOUVEAUX ANALOGUES HYDROSOLUBLES DE 20(S)-CAMPTOTHECINE
  申请人：——

  公开号：WO1997046564A1

  公开（公告）日：1997-12-11

  [EN] Novel water-soluble C-ring analogues of 20(S)-camptothecin having general formula (1). All the compounds of formula (1) are prepared from the compounds of general formula (2) having 20(S)-chiral carbon. The compounds of formula (1) possess potent anti-cancer and anti-viral properties. The invention also provides an alternate process for the preparation of known C-5 substituted compounds of formula (1).
  [FR] Nouveaux analogues de noyaux C hydrosolubles de 20(S)-camptothécine présentant la formule générale (1). Tous les composés de la formule (1) sont préparés à partir des composés de la formule générale (2) présentant un carbone 20(S)-chiral. Les composés de la formule (1) présentent des propriétés anticancéreuses et antivirales puissantes. L'invention concerne également un autre procédé de préparation de composés à substitution C-5 connus de la formule (1).