3-(1,4-Benzodioxin-2-yl)-4-(5-fluoro-1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione | 680993-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶英
• 英文名称: 3-(1,4-Benzodioxin-2-yl)-4-(5-fluoro-1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione
• 英文别名: 3-(1,4-benzodioxin-3-yl)-4-(5-fluoro-1H-indol-3-yl)-1-methylpyrrole-2,5-dione
• CAS: 680993-00-4
• 化学式: C₂₁H₁₃FN₂O₄
• 分子量: 376.344
• InChiKey: AICNCHZQIGXWFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(1,4-Benzodioxin-2-yl)-4-(5-fluoro-1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione 在 碘 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以55%的产率得到10-fluoro-7-methyl[1,4]benzodioxino[2,3-a]pyrrolo[3,4-c]carbazole-6,8-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel benzodioxinocarbazoles (BDCZs) as potential anticancer agents

  摘要：

  We report the efficient synthesis and biological evaluation of new benzodioxinoindolocarbazoles heterocycles (BDCZs) designed as potential anticancer agents. Indolic substitution and maleimide variations were performed to design a new library of BDCZs and their cytotoxicity were evaluated on two representative cancer cell lines. Several derivatives have shown a marked cytotoxicity with IC50 values in the nanomolar range. Results are reported in this Letter. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.088
• 作为产物：
  描述：

  trimethyl(1,4-benzodioxin-2-yl)tin 、 3-bromo-4-(5-fluoro-1H-indol-3-yl)-1-methylpyrrole-2,5-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.67h， 以81%的产率得到3-(1,4-Benzodioxin-2-yl)-4-(5-fluoro-1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel benzodioxinocarbazoles (BDCZs) as potential anticancer agents

  摘要：

  We report the efficient synthesis and biological evaluation of new benzodioxinoindolocarbazoles heterocycles (BDCZs) designed as potential anticancer agents. Indolic substitution and maleimide variations were performed to design a new library of BDCZs and their cytotoxicity were evaluated on two representative cancer cell lines. Several derivatives have shown a marked cytotoxicity with IC50 values in the nanomolar range. Results are reported in this Letter. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.088

文献信息

• Novel substituted [1,4] benzodioxino[2,3-e] isoindole derivatives, method for preparing and pharmaceutical compositions containing same
  申请人：Coudert Gerard

  公开号：US20060040930A1

  公开（公告）日：2006-02-23

  Compounds of formula (I): wherein: A is as defined in the description, Y represents a group selected from an oxygen atom and a methylene group, R 2 represents a hydrogen atom and in that case: R 3 represents a group selected from a hydrogen atom and the groups linear or branched (C 1 -C 6 )alkyl, aryl, aryl-(C 1 -C 6 )alkyl (in which the alkyl moiety is linear or branched) and SO 2 CF 3 , or R 2 and R 3 form a bond, R 1 represents a group selected from a hydrogen atom and the groups linear or branched (C 1 -C 6 )alkyl, aryl and aryl-(C 1 -C 6 )alkyl (in which the alkyl moiety is linear or branched) or a linear or branched (C 1 -C 6 )alkylene chain, Z 1 and Z 2 each represent a hydrogen atom or Z 1 and Z 2 , together with the carbon atoms carrying them, form a phenyl group. Medicaments.

  式(I)的化合物：其中：A如描述中定义，Y代表从氧原子和亚甲基组中选择的一个基团，R2代表氢原子，此时：R3代表从氢原子和线性或支链的(C1-C6)烷基，芳基，芳基-(C1-C6)烷基（其中烷基基团是线性或支链的）和SO2CF3中选择的一个基团，或者R2和R3形成键，R1代表从氢原子和线性或支链的(C1-C6)烷基，芳基和芳基-(C1-C6)烷基（其中烷基基团是线性或支链的）或线性或支链的(C1-C6)烷基链中选择的一个基团，Z1和Z2各自代表氢原子或Z1和Z2与携带它们的碳原子一起形成苯基。药物。
• NOUVEAUX DERIVES DE 1,4 BENZODIOXINO 2,3-e ISOINDOLE SUBSTITUES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：Les Laboratoires Servier

  公开号：EP1587810A1

  公开（公告）日：2005-10-26
• US7202255B2
  申请人：——

  公开号：US7202255B2

  公开（公告）日：2007-04-10
• [EN] NOVEL SUBSTITUTED[1,4]BENZODIOXINO[2,3-E]ISOINDOLE DERIVATIVES, METHOD FOR PREPARING SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] NOUVEAUX DERIVES DE [1,4]BENZODIOXINO[2,3-e]ISOINDOLE SUBSTITUES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：SERVIER LAB

  公开号：WO2004037831A1

  公开（公告）日：2004-05-06

  Composés de formule (I) dans laquelle : A est tel que définis dans la description, Y représente un groupement choisi parmi atome d'oxygène ou groupement méthylène, R2 représente un atome d'hydrogène, et dans ce cas R3 représente un groupement choisi parmi atome d'hydrogène, groupement alkyle (C1-C6) linéaire ou ramifié, aryle, arylalkyle (C1-C6) linéaire ou ramifié, ou SO2CF3, ou bien R2 et R3 forment une liaison, R1 représente un groupement choisi parmi atome d'hydrogène, groupement alkyle (C1-C6) linéaire ou ramifié, aryle, arylalkyle (C1-C6) linéaire ou ramifié, ou une chaîne alkylène (C1-C6) linéaire ou ramifié, Zl et Z2 représentent chacun un atome d'hydrogène ou, Zl et Z2 forment ensemble, avec les atomes de carbone qui les portent, un groupement phényle, Médicaments.