2,5-dihydro-3-(5-hydroxy-indol-3-yl)-1H-pyrrole-2,5-dione | 681163-15-5

• 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: 2,5-dihydro-3-(5-hydroxy-indol-3-yl)-1H-pyrrole-2,5-dione
• 英文别名: 3-(5-hydroxy-indol-3-yl)maleimide；3-(5-hydroxy-1H-indol-3-yl)-1H-pyrrole-2,5-dione；3-(5-hydroxy-1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 681163-15-5
• 化学式: C₁₂H₈N₂O₃
• 分子量: 228.207
• InChiKey: AGSPSMZPSFQYCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dihydro-3-(5-hydroxy-indol-3-yl)-1H-pyrrole-2,5-dione 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 xylene 为溶剂， 反应 144.0h， 生成 10-hydroxy-2H,5H,7H-1,3,4,6-tetrahydro-dipyrrolo[3,4-a:3,4-c]carbazole-1,4,6-trione
  参考文献：
  名称：

  Synthesis, in vitro antiproliferative activities, and Chk1 inhibitory properties of dipyrrolo[3,4-a:3,4-c]carbazole-triones

  摘要：

  The syntheses of dipyrrolo[3,4-a:3,4-c]carbazole-1,4,6-triones and dipyrrolo[3,4-a:3,4-c]carbazole-3,4,6-triones are reported. These compounds can be considered as granulatimide analogues in which a maleimide replaces the imidazole moiety and a five-membered lactam, ring replaces the upper maleimide. The Chk1 inhibitory properties of the more soluble compounds have been evaluated and their in vitro antiproliferative activities toward three tumor cell lines: murine leukemia L 12 10, and human colon carcinoma HT29 and HCT116. Due to their insolubility, the biological activities of the other compounds in this series could not be evaluated. All the tested compounds proved to be potent Chk1 inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.027
• 作为产物：
  描述：

  5-苄氧基吲哚 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 51.0h， 生成 2,5-dihydro-3-(5-hydroxy-indol-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of granulatimide bis-imide analogues

  摘要：

  The synthesis of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4.6-tetraones, structurally related to granulatimide is reported. These compounds can be considered as granulatimide analogues in which a maleimide heterocycle replaces the imidazole moiety. The synthesis of pyridino[2,3-b]dipyrrolo[3,4-e:3,4-g]indole-1,3,4,6-tetraones is also reported. In these compounds, a 7-azaindole unit replaces the indole moiety present in the granulatimide and isogranulatimide structures. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.101

文献信息

• [3,4-a:3,4-c]carbazole compounds
  申请人：——

  公开号：US20040077672A1

  公开（公告）日：2004-04-22

  A compound selected from those of formula (I): 1 wherein: W 1 represents, together with carbon to which it is bonded, phenyl, pyridyl, Z represents a group of formula U—V as defined in the description, Q 1 represents oxygen, NR 2 as defined in the description, Q 2 represents oxygen, NR′ 2 as defined in the description, X 1 , X 2 , X′ 1 and X′ 2 each represents hydrogen, hydroxy, alkoxy, mercapto or alkylthio, Y 1 , Y 2 , Y′ 1 and Y′ 2 each represents hydrogen, or X 1 and Y 1 , X 2 and Y 2 , X′ 1 and Y′ 1 , X′ 2 and Y′ 2 with carbon carrying them, together form carbonyl or thiocarbonyl, R 1 is as defined in the description, its isomers, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.

  从式（I）中选择的一种化合物： 其中： W1表示与其结合的碳一起，苯基，吡啶基， Z表示如描述中定义的U—V式的基团， Q1表示氧，如描述中定义的NR2， Q2表示氧，如描述中定义的NR′2， X1，X2，X′1和X′2分别表示氢，羟基，烷氧基，巯基或烷基硫基， Y1，Y2，Y′1和Y′2分别表示氢， 或者X1和Y1，X2和Y2，X′1和Y′1，X′2和Y′2与携带它们的碳一起形成羰基或硫代羰基， R1如描述中定义，其异构体，以及与药学上可接受的酸或碱形成的加合盐，以及含有这种化合物的治疗癌症的药物。
• Maleinimid-Derivate und deren Verwendung als Arzneimittel
  申请人：GÖDECKE AKTIENGESELLSCHAFT

  公开号：EP0397060A2

  公开（公告）日：1990-11-14

  Die Erfindung betrifft neue Bis-(1H-indol-3-yl)maleinimid-­Derivate, Verfahren zu deren Herstellung, Arzneimittel enthaltend diese Verbindungen und deren Verwendung zur Behandlung von Herz- und Gefäßkrankheiten wie Thrombosen, Arteriosklerose, Hypertension, von Entzündungsprozessen, Allergien, Krebs und bestimmten degenerativen Schäden des Zentralnervensystems sowie von Krankheiten des Immunsystems und viraler Erkrankungen.

  本发明涉及新的双-(1H-吲哚-3-基)马来酰亚胺衍生物、其制备工艺、含有这些化合物的药物及其在治疗心血管疾病（如血栓形成、动脉硬化、高血压、炎症过程、过敏、癌症和某些中枢神经系统变性损伤）以及免疫系统疾病和病毒性疾病中的用途。
• Synthesis and Biological Activities of New Checkpoint Kinase 1 Inhibitors Structurally Related to Granulatimide
  作者：Elisabeth Conchon、Fabrice Anizon、Bettina Aboab、Michelle Prudhomme

  DOI：10.1021/jm070664k

  日期：2007.9.1

  In the course of structure-activity relationship studies on granulatimide analogues, new pyrrolo[3,4-c]-carbazoles in which the imidazole heterocycle has been replaced by a five- or a six-membered ring bearing one or two carbonyl functions have been synthesized. Their checkpoint kinase I (Chk1) inhibitory properties and their in vitro antiproliferative activities toward three tumor cell lines-murine leukemia L1210 and human colon carcinoma HT29 and HCT116 have been determined. The results of molecular modeling in the ATP binding pocket of Chk1 are described. Among the newly synthesized compounds, compounds 13 and 16, in which the imidazole was replaced by a quinone and a hydroquinone and which bear a hydroxy.,roup on the indole moiety, are the most potent Chk1 inhibitors in this series with IC50 values of 27 and 23 nM, respectively.
• Dérivés de [3, 4 - a:3, 4-c] carbazole, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：Les Laboratoires Servier

  公开号：EP1411057B1

  公开（公告）日：2005-04-27
• US7151108B2
  申请人：——

  公开号：US7151108B2

  公开（公告）日：2006-12-19