16,17-Dimethoxy-5,7-dioxa-11-azapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaene-21-carbaldehyde | 1072927-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 16,17-Dimethoxy-5,7-dioxa-11-azapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaene-21-carbaldehyde
• CAS: 1072927-56-0
• 化学式: C₂₁H₁₅NO₅
• 分子量: 361.354
• InChiKey: ZRZOMHAWWMWFCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  16,17-Dimethoxy-5,7-dioxa-11-azapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaene-21-carbaldehyde 在 乙酸铵 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以47%的产率得到(16,17-Dimethoxy-5,7-dioxa-11-azapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaen-21-yl)methanamine
  参考文献：
  名称：

  11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents

  摘要：

  Several 11-substituted benzo[i]phenanthridine derivatives were synthesized, and their TOP1-targeting activity and cytotoxicity were assessed. Comparative data indicate that TOP1-targeting was often the primary molecular target associated with their cytotoxicity. Several 11-aminoalkyl derivatives, 11-aminocarboxy derivatives as well as the 11-[(2-dimethylamino)ethyl]carboxamide of 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine were synthesized and did exhibit considerable cytotoxicity with IC50 values ranging from 20 to 120 nM in the human lymphoblast tumor cell line RPMI8402. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.018
• 作为产物：
  描述：

  (16,17-Dimethoxy-5,7-dioxa-11-azapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaen-21-yl)methanol 在 manganese(IV) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以62%的产率得到16,17-Dimethoxy-5,7-dioxa-11-azapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaene-21-carbaldehyde
  参考文献：
  名称：

  11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents

  摘要：

  Several 11-substituted benzo[i]phenanthridine derivatives were synthesized, and their TOP1-targeting activity and cytotoxicity were assessed. Comparative data indicate that TOP1-targeting was often the primary molecular target associated with their cytotoxicity. Several 11-aminoalkyl derivatives, 11-aminocarboxy derivatives as well as the 11-[(2-dimethylamino)ethyl]carboxamide of 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine were synthesized and did exhibit considerable cytotoxicity with IC50 values ranging from 20 to 120 nM in the human lymphoblast tumor cell line RPMI8402. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.018

文献信息

• TOPOISOMERASE-TARGETING AGENTS
  申请人：LaVoie Edmond J.

  公开号：US20090258890A1

  公开（公告）日：2009-10-15

  The invention provides compounds of formula I or formula II: wherein: the bond represented by is a single bond or a double bond, and R 1 -R 5 , X, and Y have any of the meanings defined in the specification and their pharmaceutically acceptable salts. The invention also provides pharmaceutical compositions comprising a compound of formula I or II, processes for preparing compounds of formula I or II, intermediates useful for preparing compounds of formula I or II, and therapeutic methods for treating cancer and other topoisomerase related conditions using compounds of formula I or II.
• US7517867B2
  申请人：——

  公开号：US7517867B2

  公开（公告）日：2009-04-14
• US7858627B2
  申请人：——

  公开号：US7858627B2

  公开（公告）日：2010-12-28
• 11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents
  作者：Wei Feng、Mavurapu Satyanarayana、Yuan-Chin Tsai、Angela A. Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1016/j.bmc.2008.08.018

  日期：2008.9

  Several 11-substituted benzo[i]phenanthridine derivatives were synthesized, and their TOP1-targeting activity and cytotoxicity were assessed. Comparative data indicate that TOP1-targeting was often the primary molecular target associated with their cytotoxicity. Several 11-aminoalkyl derivatives, 11-aminocarboxy derivatives as well as the 11-[(2-dimethylamino)ethyl]carboxamide of 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine were synthesized and did exhibit considerable cytotoxicity with IC50 values ranging from 20 to 120 nM in the human lymphoblast tumor cell line RPMI8402. (C) 2008 Elsevier Ltd. All rights reserved.