6-hydroxy-6-methylindolo[2,1-b]quinazolin-12(6H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-hydroxy-6-methylindolo[2,1-b]quinazolin-12(6H)-one
• 英文别名: 6-Hydroxy-6-methyl-indolo[2,1-b]quinazolin-12-one；6-hydroxy-6-methylindolo[2,1-b]quinazolin-12-one
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: GTCFYZWEJXHTIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-fluoro-6-methylindolo[2,1-b]quinazolin-12(6H)-one 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以89 %的产率得到6-hydroxy-6-methylindolo[2,1-b]quinazolin-12(6H)-one
  参考文献：
  名称：

  用于合成吲哚喹唑啉酮的高效 Selectflor 介导的吲哚和邻氨基苯甲酸酯缩合

  摘要：

  吲哚与邻氨基苯甲酸盐的分子间氟环化反应在温和的反应条件下顺利进行，得到多种吲哚并喹唑啉酮结构。多种底物与该环化系统兼容。合成的氟化化合物可以通过转化为各种取代的喹唑啉酮来进行修饰，用于药物发现。此外，该方案已应用于生物活性天然生物碱 phaitanthrins A–B、cephalanthrin A 和 cruciferane 的简明全合成。

  DOI：

  10.1039/d3cc02673f

文献信息

• Synthesis of Tryptanthrins by Organocatalytic and Substrate Co-catalyzed Photochemical Condensation of Indoles and Anthranilic Acids with Visible Light and O₂
  作者：Xiangmin Li、He Huang、Chenguang Yu、Yueteng Zhang、Hao Li、Wei Wang

  DOI：10.1021/acs.orglett.6b03009

  日期：2016.11.4

  A metal-free catalytic approach to tryptanthrins has been achieved for the first time. The unique process is realized by an organocatalytic and indole and anthranilic acid substrate co-catalyzed photochemical oxidative condensation with visible light and O2. The truly environmentally friendly reaction conditions enable various reactants to participate in the process to deliver structurally diverse

  首次实现了无金属的类胰色胺的催化方法。独特的工艺是通过有机催化剂与吲哚和邻氨基苯甲酸底物与可见光和O 2共同催化光化学氧化缩合而实现的。真正的环境友好型反应条件使各种反应物都能参与该过程，从而提供结构多样的色胺酮。
• Aryne Insertion Reactions Leading to Bioactive Fused Quinazolinones: Diastereoselective Total Synthesis of Cruciferane
  作者：Sagar D. Vaidya、Narshinha P. Argade

  DOI：10.1021/ol4018062

  日期：2013.8.2

  Insertion reactions of an in situ generated arynes to a variety of suitably substituted 1,3-quinazolin-4-ones have been demonstrated for a new efficient one-step approach to a diverse range of fused quinazolinone architectures. The present protocol has been effectively utilized to accomplish the concise total synthesis of recently isolated bioactive natural products tryptanthrin, phaitanthrins A-C, and cruciferane.
• Tryptanthrin derivatives as Toxoplasma gondii inhibitors—structure–activity-relationship of the 6-position
  作者：Bogdana Krivogorsky、Amber C. Nelson、Kelsi A. Douglas、Peter Grundt

  DOI：10.1016/j.bmcl.2012.12.024

  日期：2013.2

  A panel of derivatives of the natural product tryptanthrin was synthesized and screened for its in vitro activity against the intracellular parasite Toxoplasma gondii. We concentrated on the modification of the 6-keto group of tryptanthrin and prepared a series of oximes, hydrazones and alcohols based on tryptanthrin. We evaluated parasite growth inhibition and host cell cytotoxicity. Our results indicate that in particular alcohol analogs are promising candidates for further investigation. (C) 2012 Elsevier Ltd. All rights reserved.
• Novel indolo[2,1-b]quinazoline analogues as cytostatic agents: synthesis, biological evaluation and structure–activity relationship
  作者：Vedula M. Sharma、P. Prasanna、K.V. Adi Seshu、B. Renuka、C.V. Laxman Rao、G. Sunil Kumar、C.Prasad Narasimhulu、P. Aravind Babu、R.C. Puranik、D. Subramanyam、A. Venkateswarlu、Sriram Rajagopal、K.B.Sunil Kumar、C.Seshagiri Rao、N.V.S.Rao Mamidi、Dhanvanthri S. Deevi、R. Ajaykumar、R. Rajagopalan

  DOI：10.1016/s0960-894x(02)00431-6

  日期：2002.9

  In our endeavor to design and synthesize novel anticancer agents, a new series of indoloquinazoline compounds were prepared and tested initially for anticancer activity in vitro against a panel of human cancer cell lines. Most of these compounds exhibited cytotoxic activity in in vitro screens. Compounds were selected and further evaluated using a modified Hollow Fiber Assay for their preliminary in vivo activity against 12 cell lines implanted in the subcutaneous and intraperitoneal compartments in mice. The results indicate that these compounds may constitute a new class of anticancer agents. (C) 2002 Elsevier Science Ltd. All rights reserved.
• An efficient Selectfluor-mediated condensation of indoles and anthranilates for the synthesis of indoloquinazolinones
  作者：Xinzhe Wang、Zhipeng Wu、Guogang Tu、Yuanyue Zhao、Xiaodong Xiong

  DOI：10.1039/d3cc02673f

  日期：——

  Intermolecular fluorocyclization of indoles with anthranilates, which proceeded smoothly to give diverse indoloquinazolinone architectures under mild reaction conditions, has been developed. A wide range of substrates were compatible with this cyclization system. The synthetic fluorinated compounds could be modified by their conversion to various substituted quinazolinones for drug discovery. In addition

  吲哚与邻氨基苯甲酸盐的分子间氟环化反应在温和的反应条件下顺利进行，得到多种吲哚并喹唑啉酮结构。多种底物与该环化系统兼容。合成的氟化化合物可以通过转化为各种取代的喹唑啉酮来进行修饰，用于药物发现。此外，该方案已应用于生物活性天然生物碱 phaitanthrins A–B、cephalanthrin A 和 cruciferane 的简明全合成。