Ethyl 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-carboxylate | 1028288-36-9

• 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: Ethyl 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-carboxylate
• CAS: 1028288-36-9
• 化学式: C₂₃H₁₉NO₆
• 分子量: 405.407
• InChiKey: AEFNAJHQIXFGJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  76.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 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-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 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-carboxylic acid
  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：

  2-(6,7-methylenedioxyquinolin-4-yl)-3-(4,5-dimethoxyphenyl)acrylic acid ethyl ester 在 air 、 碘 作用下， 以 苯 为溶剂， 反应 6.0h， 以35%的产率得到Ethyl 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-carboxylate
  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

• [EN] METHYLENEDIOXYBENZO [I] PHENANTHRIDINE DERIVATIVES USED TO TREAT CANCER<br/>[FR] DÉRIVÉS DE MÉTHYLÈNEDIOXYBENZO [I] PHÉNANTHRIDINE POUR TRAITER LE CANCER
  申请人：UNIV RUTGERS

  公开号：WO2010102219A1

  公开（公告）日：2010-09-10

  The invention provides compounds of formula I: wherein A, B, X, and Y have any of the values defined in the specification, as well as pharmaceutical compositions comprising such compounds, processes for preparing such compounds, and therapeutic methods for treating cancer and other topoisomerase mediated conditions.

  该发明提供了具有以下结构的化合物：其中A、B、X和Y具有规范中定义的任何值，以及包含这些化合物的药物组合物，制备这些化合物的方法，以及治疗癌症和其他拓扑异构酶介导疾病的治疗方法。
• Methylenedioxybenzo [I] phenanthridine derivatives used to treat cancer
  申请人：Rutgers, The State University of New Jersey

  公开号：US10179789B2

  公开（公告）日：2019-01-15

  The invention provides compounds of formula I: wherein A, B, X, and Y have any of the values defined in the specification, as well as pharmaceutical compositions comprising such compounds, processes for preparing such compounds, and therapeutic methods for treating cancer and other topoisomerase mediated conditions.

  本发明提供了式 I 的化合物： 其中A、B、X和Y具有说明书中定义的任何值，以及包含此类化合物的药物组合物、制备此类化合物的工艺和治疗癌症及其他拓扑异构酶介导的病症的治疗方法。
• Topoisomerase-targeting agents
  申请人：LaVoie J. Edmond

  公开号：US20070225289A1

  公开（公告）日：2007-09-27

  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.
• 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.
• METHYLENEDIOXYBENZO [I] PHENANTHRIDINE DERIVATIVES USED TO TREAT CANCER
  申请人：LaVoie Edmond J.

  公开号：US20120101117A1

  公开（公告）日：2012-04-26

  The invention provides compounds of formula I: wherein A, B, X, and Y have any of the values defined in the specification, as well as pharmaceutical compositions comprising such compounds, processes for preparing such compounds, and therapeutic methods for treating cancer and other topoisomerase mediated conditions.