5,10-dihydroindeno<1,2-b>indol-10-one | 53904-16-8

• 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: 5,10-dihydroindeno<1,2-b>indol-10-one
• 英文别名: 5H,10H-indeno[1,2-b]indol-10-one；indeno[1,2-b]indol-10(5H)-one；5H-indeno[1,2-b]indol-10-one；indeno[1,2]indole-10(5H)-one；5H-indeno[1,2-b]indol-10-one；Inden<1,2-b>indol-10(5H)-on
• CAS: 53904-16-8
• 化学式: C₁₅H₉NO
• 分子量: 219.243
• InChiKey: NHOZLQCFHOVMLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,10-dihydroindeno<1,2-b>indol-10-one 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 indeno[1,2-b]indol-10(5H)-one oxime
  参考文献：
  名称：

  Indenoindolone derivatives as topoisomerase II–inhibiting anticancer agents

  摘要：

  Based on known heterocyclic topoisomerase II inhibitors and anticancer agents, various indenoindolone derivatives were predicted as potential topoisomerase II-inhibiting anticancer agents. They are hydrazones, (thio)semicarbazones, and oximes of indenoindolones, and indenoindolols. These derivatives with suitable substitutions exhibited potent specific inhibition of human DNA TopoII alpha, while not showing inhibition of topoisomerase I and DNA intercalation, despite the fact that parent indenoindolones are known poor/moderate inhibitors of topoisomerase II. The potent topoisomerase II inhibitor indenoindolone derivatives exhibited good anticancer activities compared to etoposide and 5-fluorouracil, and relatively low toxicity to normal cells. These derivatizations of indenoindolones were found to result in enhancement of anticancer activities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.063
• 作为产物：
  描述：

  苯茚二酮 在 sodium azide 、 三氯氧磷 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 5.5h， 生成 5,10-dihydroindeno<1,2-b>indol-10-one
  参考文献：
  名称：

  3-叠氮基-2-苯基-茚满-1-酮热环化为5 h-茚并[1,2 - b ]吲哚-10-one †

  摘要：

  3-叠氮基-2-苯基茚-1-酮（4），其从3-氯-2-苯基茚-1-酮（得3），热解上环化从而5 ħ -茚并[1,2 b ]吲哚-10-一个（5）。3-azido-2-phenylindan-1-one（4）与三苯基膦反应生成2-phenyl-3-（triphenylphosphoranylideneaminoamino）-indan-1-one（6），可以将其水解为3-amino-2-phenylindan -1-一（7）。尝试对3-chloro-2-pyridylindan-1-ones执行类似的环化序列失败。

  DOI：

  10.1002/jhet.5570390119

文献信息

• Indenoindolone compounds
  申请人：——

  公开号：US20020173531A1

  公开（公告）日：2002-11-21

  Compound of formula (I): 1 wherein: R represents hydrogen or a group selected from alkenyl and optionally substituted alkyl, each of R 1 to R 8 , which may be identical or different, represents hydrogen or a group selected from alkyl, alkenyl, hydroxy, alkoxy, alkenyloxy, arylalkyl, arylalkoxy, carboxy, acyloxy and arylcarbonyloxy, or one of R 1 to R 8 forms with an adjacent one R 1 to R 8 an alkylenedioxy group, its optical isomers when they exist, and addition salts thereof with a pharmaceutically acceptable acid or base, with the proviso that: when R does not represent hydrogen, then at least one of R 1 to R 8 represents hydroxy or acyloxy, and the compounds of formula (I) are other than indeno[1,2-b]indol-10(5H)-one. Medicinal products containing the same which are useful for treatment of disorders of the melatoninergic system.

  化合物的化学式（I）如下：其中：R代表氢或从烯基和可选择的取代烷基中选择的基团，R1到R8中的每一个，可能相同也可能不同，代表氢或从烷基、烯基、羟基、烷氧基、烯基氧基、芳基烷基、芳基氧基、羧基、酰氧基和芳基羰氧基中选择的基团，或者R1到R8中的一个与相邻的R1到R8形成烷二氧基基团，其光学异构体（存在时）及其与药学上可接受的酸或碱形成的加合物，但条件是：当R不代表氢时，那么至少R1到R8中的一个代表羟基或酰氧基，化合物的化学式（I）不包括吲哚[1,2-b]吲哚-10(5H)-酮。含有该化合物的药物用于治疗褪黑素系统紊乱。
• Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems
  作者：Natalia Chernyak、David Tilly、Zhou Li、Vladimir Gevorgyan

  DOI：10.1039/b919991h

  日期：——

  possessing fused seven-membered rings were efficiently synthesized via the Pd-catalyzed intramolecular carbopalladation-annulation of 3-(2-iodobenzyl)-indoles and alkynes. A remarkable base effect on the chemoselectivity of this transformation has been found: switching from Et(3)N to CsOAc completely reverses the reaction path to intramolecular cyclization forming fused five-membered rings.

  通过 Pd 催化的 3-(2-碘苄基)-吲哚和炔烃的分子内碳钯化-环化有效合成了具有稠合七元环的多环吲哚结构。已经发现对这种转化的化学选择性的显着基础效应：从 Et(3)N 切换到 CsOAc 完全逆转了分子内环化形成稠合五元环的反应路径。
• Synthesis of Fluoren-9-ones by the Palladium-Catalyzed Cyclocarbonylation of <i>o</i>-Halobiaryls
  作者：Marino A. Campo、Richard C. Larock

  DOI：10.1021/jo020140m

  日期：2002.8.1

  The synthesis of various substituted fluoren-9-ones has been accomplished by the palladium-catalyzed cyclocarbonylation of o-halobiaryls. The cyclocarbonylation of 4'-substituted 2-iodobiphenyls produces very high yields of 2-substituted fluoren-9-ones bearing either electron-donating or electron-withdrawing substituents. 3'-Substituted 2-iodobiphenyls afford 3-substituted fluoren-9-ones in excellent

  各种取代的芴-9-酮的合成已通过邻卤代联芳基的钯催化环羰基化完成。4′-取代的2-碘联苯的环羰基化产生非常高产率的带有给电子或吸电子取代基的2-取代的芴-9-。3'-取代的2-碘联苯以优异的产率和良好的区域选择性提供3-取代的芴-9-一。该化学方法已成功地扩展到多环芴酮和含有稠合异喹啉，吲哚，吡咯，噻吩，苯并噻吩和苯并呋喃环的芴酮。
• An Easy Access to Carbazolones and 2,3-Disubstituted Indoles
  作者：Donala Janreddy、Veerababurao Kavala、J. W. John Bosco、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.1002/ejoc.201001357

  日期：2011.4

  Synthesis of carbazol-4-ones, 3,4-dihydrocyclopental-indol-1-one, and indole derivatives by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation of 3-hydroxy-2-(2-nitrophenyl)enones is demonstrated. The same protocol has been extended to access indolocarbazolone and indoloquinolone derivatives.

  通过 Fe/AcOH 介导的 3-羟基-2-(2-硝基苯基) 烯酮的分子内还原 N-杂环化合成 carbazol-4-ones、3,4-dihydrocyclopental-indol-1-one 和吲哚衍生物. 相同的协议已扩展到获取吲哚并咔唑酮和吲哚喹诺酮衍生物。
• Friedel-Crafts 3-(2-Bromobenzoylation) of Indoles and Intramolecular Direct Arylation: An Efficient Route to Indenoindolones
  作者：Sankar Guchhait、Maneesh Kashyap

  DOI：10.1055/s-0031-1289663

  日期：2012.2

  Friedel-Crafts reaction of 2-bromobenzoyl chlorides with indoles to give 3-(2-bromobenzoyl)indoles and their palladium-catalyzed intramolecular direct arylation to give indenoindolones, has been developed. 3-(2-Bromobenzoyl)indoles were crucial intermediates; the method was successful with N-unprotected or N-protected indoles. This approach affords a convenient preparation of diverse substituted and functionalized

  已经开发出一种有效的两步法，包括2-溴苯甲酰氯与吲哚的弗瑞德-克来福特反应，得到3-（2-溴苯甲酰基）吲哚，以及它们的钯催化的分子内直接芳基化，得到茚并吲哚酮。3-（2-溴苯甲酰基）吲哚是关键的中间体。该方法适用于N-未保护或N-保护的吲哚。该方法提供了从容易获得的起始原料以高收率到高收率方便地制备各种取代的和官能化的茚并吲哚酮的方法。通过该合成可以容易地掺入通常整合到生物活性化合物中的几个部分。 酰化-芳基化-催化-偶联-杂环-吲哚-路易斯酸-钯