4,11-dimethoxy-1-methylnaphtho[2,3-f]indole-5,10-dione | 354118-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,11-dimethoxy-1-methylnaphtho[2,3-f]indole-5,10-dione
• 英文别名: 4,11-dimethoxy-1-methyl 1H-naphtho[2,3-f]indole-5,10-dione；N-methylnaphtho-[2,3-f]indole-5,10-dione
• CAS: 354118-55-1
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: TVKYRIIRAUWHNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  57.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,11-dimethoxy-1-methylnaphtho[2,3-f]indole-5,10-dione 在 磺酰氯 、 水 、 sodium acetate 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 25.0h， 以65%的产率得到4,11-dimethoxy-1-methyl-1H-naphtho[2,3-f]indole-2,3,5,10-tetraone
  参考文献：
  名称：

  Heterocyclic analogs of 5,12-naphthacenequinone 9*. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones

  摘要：

  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.

  DOI：

  10.1007/s10593-011-0740-1
• 作为产物：
  描述：

  4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到4,11-dimethoxy-1-methylnaphtho[2,3-f]indole-5,10-dione
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1017567317083

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。