1-(4-氯苄基)-5-甲基-1H-吲哚-2,3-二酮 | 303998-01-8

• 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
• 中文名称: 1-(4-氯苄基)-5-甲基-1H-吲哚-2,3-二酮
• 英文名称: 1-(4-chlorobenzyl)-5-methylindoline-2,3-dione
• 英文别名: 1-(4-chlorobenzyl)-5-methyl-1H-indole-2,3-dione；1-[(4-chlorophenyl)methyl]-5-methylindole-2,3-dione
• CAS: 303998-01-8
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: VSQRATQPXJILRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-氯苄基)-5-甲基-1H-吲哚-2,3-二酮 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 以95 %的产率得到1-(4-chlorobenzyl)-6-methyl-2H-benzo[d][1,3]oxazine-2,4(1H)-dione
  参考文献：
  名称：

  Discovery of novel series of 4-quinolone hybrids as multi-targeting agent: Design, synthesis and H1-antihistaminic activity to treat allergic asthma

  摘要：

  DOI：

  10.1016/j.molstruc.2023.136241
• 作为产物：
  描述：

  乙烷,三氯氟- 在 盐酸 、 盐酸羟胺 、 sodium hydride 、 sodium sulfate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 12.5h， 生成 1-(4-氯苄基)-5-甲基-1H-吲哚-2,3-二酮
  参考文献：
  名称：

  Synthesis and evaluation of 3-ylideneoxindole acetamides as potent anticancer agents

  摘要：

  Indirubin, an active component in the traditional Chinese medicine formula Danggui Longhui Wan, shows promising anticancer effects. Meisoindigo is an analog derived from indirubin, which is less toxic and appears to be even more potent against cancer. In considering meisoindigo as a structural template for the development of new drugs, we designed and synthesized a series of 3-ylideneoxindole acetamides as novel anticancer agents. The acetamides were then evaluated for in vitro and in vivo anticancer activities. The 3-ylideneoxindole acetamides were found to have better anticancer activity than was indirubin-3'-oxime in several cancer cell lines and also displayed a spectrum of activity similar to that of the drug candidate roscovitine, a CDK inhibitor. Among the 3-ylideneoxindole acetamides, compound 10 showed particularly good efficacy. Cell cycle analysis further revealed that compound 10 arrested cells in the G1 phase and caused an increase in the sub-G1 population, indicating that the apoptosis pathway had been induced. In addition, exposure of cells to compound 10 led to the upregulation of the cell-cycle regulator cyclin D1, which was sustained at a high level. In contrast, the same compound induced a short-term elevation in the level of cyclin E, which was followed by a rapid decrease and the attenuation of Rb phosphorylation. Furthermore, a docking model suggests that compound 10 binds to the active site of CDK4. In testing the therapeutic potency of compound 10 on CT26-xenografted BALB/c mice, a significant reduction in tumor size comparable to that of cisplatin was found when administrated via the i.p. route. The mice presented no loss of body weight, indicating that this compound possesses low toxicity. In the future, we are planning in vivo investigations of these new active anticancer agents to better elucidate active mechanisms at the cellular level and thus benefit the development of anticancer therapies. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.062

文献信息

• Synthesis of diverse isatins via ring contraction of 3-diazoquinoline-2,4-diones
  作者：Rajeev Shrestha、Gun Joon Lee、Yong Rok Lee

  DOI：10.1039/c6ra13585d

  日期：——

  An efficient synthesis of diverse isatin derivatives was accomplished by a copper-mediated reaction of 3-diazoquinoline-2,4-diones via ring contraction through domino Wolff rearrangement, decarboxylation, bromination, substitution, and dehydration. This protocol has several advantages as a one-pot procedure, with functional group tolerance, and high yield.

  通过铜介导的多米诺夫·沃尔夫重排，脱羧，溴化，取代和脱水，通过环介导的3-重氮喹啉-2,4-二酮的铜介导反应，完成了各种靛红衍生物的有效合成。该协议作为一锅法具有几个优点，具有官能团耐受性和高收率。
• Oxindole compounds and their uses as therapeutic agents
  申请人：Chafeev Mikhail

  公开号：US20070105820A1

  公开（公告）日：2007-05-10

  This invention is directed to oxindole compounds that are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of using the compounds are also disclosed.

  本发明涉及氧化吲哚化合物，其对钠通道介导的疾病或病状，如疼痛的治疗和/或预防有用。还公开了包含该化合物的制药组合物和使用该化合物的方法。
• Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain
  作者：Idan Chiyanzu、Elizabeth Hansell、Jiri Gut、Philip J. Rosenthal、James H. McKerrow、Kelly Chibale

  DOI：10.1016/s0960-894x(03)00756-x

  日期：2003.10

  While commercial isatins were practically inactive against the target proteases, thiosemicarbazone derivatives were found to be active. The most active compound from the series displayed an inhibitory IC50 value of 1 muM against rhodesain. One thiosemicarbazone was found to be active against all three proteases with inhibitory IC50 values of 10 muM or less. A combination of N-benzylation and appropriate substitution on the aromatic portion of the isatin scaffold was generally found to be beneficial especially against cruzain for ketone inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.
• OXINDOLE COMPOUNDS AND THEIR USES AS THERAPEUTIC AGENTS
  申请人：XENON PHARMACEUTICALS INC.

  公开号：EP1877378A2

  公开（公告）日：2008-01-16
• [EN] OXINDOLE COMPOUNDS AND THEIR USES AS THERAPEUTIC AGENTS<br/>[FR] COMPOSES D'OXINDOLE ET LEURS UTILISATIONS COMME AGENTS THERAPEUTIQUES
  申请人：XENON PHARMACEUTICALS INC

  公开号：WO2006113864A2

  公开（公告）日：2006-10-26

  [EN] This invention is directed to oxindole compounds that are useful for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain. Pharmaceutical compositions comprising the compounds and methods of using the compounds are also disclosed.
  [FR] L'invention concerne des composés d'oxindole utilisés pour le traitement et/ou la prévention de maladies ou de pathologies induites par le canal de sodium, notamment les douleurs. L'invention concerne également des compositions pharmaceutiques comprenant les composés et des procédés d'utilisation des composés.