5,7-dibromo-1-(2-naphthylmethyl)-1H-indole-2,3-dione | 1020265-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,7-dibromo-1-(2-naphthylmethyl)-1H-indole-2,3-dione
• 英文别名: 5,7-dibromo-N-(naphthalene-2-ylmethyl)isatin；5,7-dibromo-1-(naphthalen-2-ylmethyl)indole-2,3-dione
• CAS: 1020265-01-3
• 化学式: C₁₉H₁₁Br₂NO₂
• 分子量: 445.11
• InChiKey: WRIGNTQVYJCSMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,7-二溴靛红 、 2-溴甲基萘 在 sodium hydride 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以64%的产率得到5,7-dibromo-1-(2-naphthylmethyl)-1H-indole-2,3-dione
  参考文献：
  名称：

  N-Phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents

  摘要：

  A range of N-phenethyl, N-phenacyl, and N-(1- and 2-naphthylmethyl) derivatives of 5,7-dibromoisatin 2 were prepared by N-alkylation reactions. Their activity against human monocyte-like histiocytic lymphoma (U937), leukemia (Jurkat), and breast carcinoma (MDA-MB-231) cell lines was assessed. The results allowed further development of structure-activity relationships. The compound 5,7-dibromo-N-(1-naphthylmethyl)-1H-indole-2,3-dione 5a was the most potent against U937 cells with an IC50 value of 0.19 mu M. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.026

文献信息

• [EN] SELECTIVELY DELIVERABLE ISATIN-BASED CYTOTOXIC AGENTS<br/>[FR] AGENTS CYTOTOXIQUES À BASE D'ISATINE POUVANT ÊTRE ADMINISTRÉS SÉLECTIVEMENT
  申请人：UNIV WOLLONGONG

  公开号：WO2008074078A1

  公开（公告）日：2008-06-26

  [EN] The invention relates to compounds comprising a cytotoxic isatin derivative conjugated to a cell targeting moiety via a spacer group. These conjugates allow the cytotoxic isatin derivaties to be targeted to particular cell and tissue types. The invention also relates to novel isatin derivatives, intermediates used in preparing the conjugates and method of using the conjugates.
  [FR] L'invention concerne des composés contenant un dérivé d'isatine cytotoxique conjugué à un groupe fonctionnel de ciblage cellulaire au moyen d'un groupe espaceur. Ces conjugués permettent de cibler les dérivés d'isatine cytotoxiques sur des types de cellules et de tissus particuliers. L'invention concerne également de nouveaux dérivés d'isatine, des intermédiaires employés dans la préparation des conjugués et un procédé d'utilisation des conjugués.
• N-Phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents
  作者：Lidia Matesic、Julie M. Locke、John B. Bremner、Stephen G. Pyne、Danielle Skropeta、Marie Ranson、Kara L. Vine

  DOI：10.1016/j.bmc.2007.12.026

  日期：2008.3.15

  A range of N-phenethyl, N-phenacyl, and N-(1- and 2-naphthylmethyl) derivatives of 5,7-dibromoisatin 2 were prepared by N-alkylation reactions. Their activity against human monocyte-like histiocytic lymphoma (U937), leukemia (Jurkat), and breast carcinoma (MDA-MB-231) cell lines was assessed. The results allowed further development of structure-activity relationships. The compound 5,7-dibromo-N-(1-naphthylmethyl)-1H-indole-2,3-dione 5a was the most potent against U937 cells with an IC50 value of 0.19 mu M. (C) 2007 Elsevier Ltd. All rights reserved.