5-methoxy-4-nitro-1-(3',4',5'-trimethoxybenzoyl)indole | 1041752-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-methoxy-4-nitro-1-(3',4',5'-trimethoxybenzoyl)indole
• 英文别名: (5-Methoxy-4-nitroindol-1-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1041752-21-9
• 化学式: C₁₉H₁₈N₂O₇
• 分子量: 386.361
• InChiKey: HQLARSCXOWQGCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-methoxy-4-nitro-1-(3',4',5'-trimethoxybenzoyl)indole 在 铁粉 、 氯化铵 作用下， 以 水 、 异丙醇 为溶剂， 反应 3.0h， 以72%的产率得到4-amino-5-methoxy-1-(3',4',5'-trimethoxybenzoyl)indole
  参考文献：
  名称：

  Discovery of 4-Amino and 4-Hydroxy-1-aroylindoles as Potent Tubulin Polymerization Inhibitors

  摘要：

  1-Aroylindoline, 1-aroyl-1,2,3,4-tetrahydroquinoline, and 1-aroylindole derivatives were synthesized and evaluated for anticancer activity. The 4-amino and 4-hydroxy-1-aroylindoles 26 and 27 with IC(50) Of 0.9 and 0.6 mu M, respectively, exhibited antitubulin activity superior or comparable to that of colchicine and combretastatin A-4. They also showed antiproliferative activity with IC(50) of 0.3-5.4 nM in a set of human cancer cell lines.

  DOI：

  10.1021/jm800150d
• 作为产物：
  描述：

  、 3,4,5-三甲氧基苯甲酸酐 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到5-methoxy-4-nitro-1-(3',4',5'-trimethoxybenzoyl)indole
  参考文献：
  名称：

  Discovery of 4-Amino and 4-Hydroxy-1-aroylindoles as Potent Tubulin Polymerization Inhibitors

  摘要：

  1-Aroylindoline, 1-aroyl-1,2,3,4-tetrahydroquinoline, and 1-aroylindole derivatives were synthesized and evaluated for anticancer activity. The 4-amino and 4-hydroxy-1-aroylindoles 26 and 27 with IC(50) Of 0.9 and 0.6 mu M, respectively, exhibited antitubulin activity superior or comparable to that of colchicine and combretastatin A-4. They also showed antiproliferative activity with IC(50) of 0.3-5.4 nM in a set of human cancer cell lines.

  DOI：

  10.1021/jm800150d

文献信息

• HETEROCYCLIC COMPOUNDS AS DCTPP1 MODULATORS
  申请人：Thomas Helledays Stiftelse För Medicinsk Forskning

  公开号：EP3204362A1

  公开（公告）日：2017-08-16
• [EN] HETEROCYCLIC COMPOUNDS AS DCTPP1 MODULATORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES EN TANT QUE MODULATEURS DCTPP1
  申请人：THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING

  公开号：WO2016055582A1

  公开（公告）日：2016-04-14

  The invention relates to compoundsof formula I, or a pharmaceutically-acceptable salt thereof. The present invention also relates to pharmaceutical formulations comprising these compounds, and to their use as medicaments for the treatment of disorders where modulation of DCTPP (deoxycytidine triphosphate pyrophosphatase 1) activity exerts a therapeutic effect.
• Discovery of 4-Amino and 4-Hydroxy-1-aroylindoles as Potent Tubulin Polymerization Inhibitors
  作者：Jing-Ping Liou、Zi-Yi Wu、Ching-Chuan Kuo、Chi-Yen Chang、Pei-Yi Lu、Chi-Ming Chen、Hsing-Pang Hsieh、Jang-Yang Chang

  DOI：10.1021/jm800150d

  日期：2008.7.1

  1-Aroylindoline, 1-aroyl-1,2,3,4-tetrahydroquinoline, and 1-aroylindole derivatives were synthesized and evaluated for anticancer activity. The 4-amino and 4-hydroxy-1-aroylindoles 26 and 27 with IC(50) Of 0.9 and 0.6 mu M, respectively, exhibited antitubulin activity superior or comparable to that of colchicine and combretastatin A-4. They also showed antiproliferative activity with IC(50) of 0.3-5.4 nM in a set of human cancer cell lines.