5-benzyl-5H-indeno[1,2-b]indole-6,9,10-trione | 1018686-95-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-benzyl-5H-indeno[1,2-b]indole-6,9,10-trione
• 英文别名: 5-benzyl-5,6,9,10-tetrahydroindeno[1,2-b]indole-6,9,10-trione；5-Benzylindeno[1,2-b]indole-6,9,10-trione
• CAS: 1018686-95-7
• 化学式: C₂₂H₁₃NO₃
• 分子量: 339.35
• InChiKey: JGAMCAFOBDTYOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 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：
  56.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-benzyl-3-amino-2-cyclohexen-1-one 在 salcomine 、 N,N,N',N'-tetramethylsulfurous acid diamine 、 氧气 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 5-benzyl-5H-indeno[1,2-b]indole-6,9,10-trione
  参考文献：
  名称：

  Novel indeno[1,2-b]indoloquinones as inhibitors of the human protein kinase CK2 with antiproliferative activity towards a broad panel of cancer cell lines

  摘要：

  We previously reported indeno[1,2-b]indoles as a novel class of potent inhibitors of the human protein kinase CK2. In the present study we prepared two novel quinoid derivatives, the indeno[1,2-b]indoloquinones 6b and 6c, and demonstrated inhibition of the human CK2 by the compounds. Furthermore, we showed substantial antiproliferative activity of both compounds towards a broad panel of human cancer cell lines in the low micromolar range. Whereas the earlier indeno[1,2-b]indoles have been shown to be selective for CK2, the indeno[1,2-b]indoloquinones 6b and 6c also inhibited the AMPK activated protein kinase ARK5, potentially contributing to the anti-cancer effects of the compounds. In addition, with compound 6b we found a very potent inhibitor of the leukemia-associated receptor tyrosine kinase FLT3, with an IC50 of 0.18 mu M. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2012.06.068

文献信息

• SUBSTITUTED INDENO[1,2-B]INDOLE DERIVATIVES AS NOVEL INHIBITORS OF PROTEIN KINASE CK2 AND THEIR USE AS TUMOR THERAPEUTIC AGENTS, CYTOSTATICS AND DIAGNOSTIC AIDS
  申请人：Hemmerling Hans-Jorg

  公开号：US20100056599A1

  公开（公告）日：2010-03-04

  Synthesis of novel substituted indeno[1,2-b]indole derivatives of the type of 5,6,7,8-tetrahydroindeno[1,2-b]indole-9,10-diones and 5H-indeno[1,2-b]indole-6,9,10-triones, which show pronounced inhibition of the human protein kinase CK2, and the use thereof as active ingredients in medicaments and/or drug products in particular for the treatment of neoplastic diseases.

  合成新型取代的indeno[1,2-b]indole衍生物，包括5,6,7,8-四氢indeno[1,2-b]indole-9,10-二酮和5H-indeno[1,2-b]indole-6,9,10-三酮。这些衍生物表现出显著的抑制人类蛋白激酶CK2的作用，并可作为药物中的活性成分，特别用于治疗肿瘤性疾病。
• SUBSTITUIERTE INDENO[1,2-B]INDOLDERIVATE ALS NEUE HEMMSTOFFE DER PROTEIN KINASE CK2 UND IHRE VERWENDUNG ALS TUMORTHERAPEUTIKA, CYTOSTATIKA UND DIAGNOSTIKA
  申请人：Heinrich-Heine-Universität Düsseldorf

  公开号：EP2079691A1

  公开（公告）日：2009-07-22
• US8133913B2
  申请人：——

  公开号：US8133913B2

  公开（公告）日：2012-03-13
• [DE] SUBSTITUIERTE INDENO[1,2-B]INDOLDERIVATE ALS NEUE HEMMSTOFFE DER PROTEIN KINASE CK2 UND IHRE VERWENDUNG ALS TUMORTHERAPEUTIKA, CYTOSTATIKA UND DIAGNOSTIKA<br/>[EN] SUBSTITUTED INDENO[1,2-B]INDOLE DERIVATIVES AS NOVEL INHIBITORS OF PROTEIN KINASE CK2 AND THEIR USE AS TUMOUR THERAPEUTIC AGENTS, CYTOSTATICS AND DIAGNOSTIC AIDS<br/>[FR] DÉRIVÉS D'INDÉNO[1,2-B]INDOLE SUBSTITUÉS COMME NOUVEAUX INHIBITEURS DE LA PROTÉINE KINASE CK2 ET LEUR UTILISATION COMME AGENTS ANTITUMORAUX, CYTOSTATIQUES ET DIAGNOSTIQUES
  申请人：UNIV DUESSELDORF H HEINE

  公开号：WO2008040547A1

  公开（公告）日：2008-04-10

  [EN] Synthesis of novel substituted indeno[1,2-b]indole derivatives of the type of 5,6,7,8-tetrahydroindeno[1,2-b]indole-9,10-diones and 5H-indeno[1,2-b]indole-6,9,10-triones, which show pronounced inhibition of the human protein kinase CK2, and the use thereof as active ingredients in medicaments and/or drug products in particular for the treatment of neoplastic diseases.
  [FR] Synthèse de nouveaux dérivés d'indéno[1,2 b-]indole substitués du type des 5,6,7,8-tétrahydroindéno[1,2-b]indol-9,10-diones et des 5H-indéno-[1,2-b]indol-6,9,10-triones, qui présentent un effet marqué d'inhibition de la protéine kinase CK2 humaine, et leur utilisation comme principes actifs de médicaments et/ou agents thérapeutiques, notamment pour le traitement d'affections néoplasiques.
  [DE] Synthese neuer substituierter lndeno[1,2 b-]indolderivate vom Typ 5,6,7,8- Tetrahydro-indeno[1,2-b]indol-9,10-dione und 5H-lndeno[1,2-b]indol-6,9,10- trione, die eine ausgeprägte Inhibition der humanen Protein Kinase CK2 zeigen, und deren Verwendung als Wirkstoffe in Medikamenten und/oder Arzneimitteln insbesondere zur Behandlung von neoplastischen Erkrankungen.