4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione | 184529-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione
• 英文别名: 4,11-dimethoxy-1H-naphtho[2,3-f]indole-5,10-dione
• CAS: 184529-69-9
• 化学式: C₁₈H₁₃NO₄
• 分子量: 307.306
• InChiKey: FPAIXTBQZHRAST-UHFFFAOYSA-N

物化性质

• 沸点：
  579.3±50.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione 在 cerium(III) chloride 、 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 1-[3-chloropropyl]-4,11-dihydroxy-1H-naphtho[2,3-f]indole-5,10-dione
  参考文献：
  名称：

  Synthesis of 1-(ω-aminoalkyl)naphthoindolediones with antiproliferative properties

  摘要：

  The preparation and cytotoxic properties of 4,11-dihydroxynaphtho[2,3-f]indole-5,10-dione derivatives carrying N-aminoalkyl substituents are described. The N-aminobutylnaphthoindolediones obtained were studied in National Cancer Institute Screening Program and demonstrated high antiproliferative activity against 60 human cancer cell lines. All N-(4-aminobutyl) derivatives have higher potency than adriamycin or mitoxantrone against adriamycin selected multidrug resistant breast cancer cell line NCI/ADR. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.042
• 作为产物：
  描述：

  1,4-dimethoxy-3-methyl anthracene-9,10-dione 在 硝酸 、 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.75h， 生成 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione
  参考文献：
  名称：

  Naphthomoles. 7. Synthesis of 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione and 4-methoxynaphtho[2,3-f]-indole-5,10-dione

  摘要：

  DOI：

  10.1007/bf01176964

文献信息

• Synthesis and structure–activity relationship studies of 4,11-diaminonaphtho[2,3-f]indole-5,10-diones
  作者：Andrey E. Shchekotikhin、Valeria A. Glazunova、Yuri N. Luzikov、Vladimir N. Buyanov、Olga Yu. Susova、Alexander A. Shtil、Maria N. Preobrazhenskaya

  DOI：10.1016/j.bmc.2006.03.052

  日期：2006.8

  We describe the synthesis of derivatives of 4,11-diaminonaphtho[2,3-f]indole-5,10-dione and their cytotoxicity for human tumor cells that express major determinants of altered anticancer drug response, the efflux pump P-glycoprotein, and non-functional p53. Nucleophilic substitution of methoxy groups in 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione with various ethylenediamines yielded the derivatives

  我们描述了4,11-二氨基萘[2,3-f]吲哚-5,10-二酮衍生物的合成及其对人肿瘤细胞的细胞毒性，这些细胞表达改变的抗癌药物反应的主要决定因素，外排泵P糖蛋白，和无功能的p53。用各种乙二胺对4,11-二甲氧基萘[2,3-f]吲哚-5,10-二酮中的甲氧基进行亲核取代，得到4,11-二氨基萘[2,3-f]吲哚-5,10-的衍生物二酮，其吲哚含有抗肿瘤药金刚酮的类似物。新化合物对表达多药耐药性，表达P-糖蛋白的肿瘤细胞的细胞毒性高度依赖于乙二胺部分末端氨基处的N-取代基。相对于野生型p53，p53无效结肠癌细胞对参考药物阿霉素的敏感性较低，
• Heterocyclic analogs of 5,12-naphtacenequinone 13*. Synthesis of 4,11-diaminoanthra[2,3-b]furan-5,10-diones and sulfur-containing analogs
  作者：Alexander S. Tikhomirov、Eugeny E. Bykov、Yury N. Luzikov、Alexander M. Korolev、Andrey E. Shchekotikhin

  DOI：10.1007/s10593-016-1968-6

  日期：2016.10

  We have developed an effective method for the synthesis of 4,11-diaminoanthra[2,3-b]furan-5,10-dione and 4,11-diaminoanthra[2,3-b]-thiophene-5,10-dione derivatives based on the substitution of 4,11-alkoxy groups with n-butylamine and subsequent oxidative dealkylation of n-butylamino groups via treatment with tetrabutylammonium hydroxide in DMSO.

  我们已经开发出一种合成4,11-二氨基蒽[2,3- b ]呋喃-5,10-二酮和4,11-二氨基蒽[2,3 - b ]-噻吩-5,10-二酮的有效方法衍生物是基于用正丁胺取代4,11-烷氧基，然后通过在DMSO中用氢氧化四丁铵处理正丁氨基的氧化脱烷基而得到的衍生物。
• Reductive elimination of alkoxy group in anthraquinone derivatives
  作者：Alexander S. Tikhomirov、Daria V. Andreeva、Andrey E. Shchekotikhin

  DOI：10.1016/j.tet.2022.132957

  日期：2022.9

  Anthraquinone derivatives are constantly in a focus of synthetic chemists due to a diversity of valuable biological, photochemical and redox properties. However, quinone core limits applicability of chemical transformations making a search for new methods of modification of anthraquinones highly demanded. A convenient approach of regioselective reductive α-alkoxy group cleavage of anthraquinone derivatives

  由于具有多种有价值的生物、光化学和氧化还原特性，蒽醌衍生物一直是合成化学家关注的焦点。然而，醌核心限制了化学转化的适用性，因此迫切需要寻找新的蒽醌修饰方法。开发并评估了一种方便的区域选择性还原 α-烷氧基裂解蒽醌衍生物的方法。最有效的转化是通过醌部分的锌还原和酸性介质中的质子重排，然后是烷氧基的消除。蒽醌核心β位上的强供体对于转化至关重要，并且仅提供从α的消除-位置。该方法简化了一些具有生物活性的1,3-取代蒽醌的获取，并应用于天然产物的合成，例如1-甲基芸香苷、1,2-二甲基蒽酚蒽醌和去莨菪醇。
• Heterocyclic analogs of 5,12-naphthacenequinone 9*. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones
  作者：A. N. Nikitina、A. E. Shchekotikhin、Y. N. Luzikov、A. M. Korolev、V. N. Buyanov、M. N. Preobrazhenskaya

  DOI：10.1007/s10593-011-0740-1

  日期：2011.5

  A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-diones. Successive halogenation using phosphorus pentachloride and acylation of tert-butylamine by the intermediate 2-chloro derivative converted 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-dione to the 2-amino-3H-naphtho[2,3-f]indole-3,5,10-trione derivative.
• Naphthoindoles. 8. Electrophilic substitution reactions of 4,11-dimethyxynaphtho[2,3-f]indole-5,10-dione
  作者：A. E. Shchekotikhin、E. P. Baberkina、V. N. Buyanov、K. F. Turchin、N. N. Suvorov

  DOI：10.1007/bf02251688

  日期：1998.7