6-hydroxy-6-(2-oxopropyl)indolo[2,1-b]quinazolin-12(6H)-one | 1033722-02-9

• 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-(2-oxopropyl)indolo[2,1-b]quinazolin-12(6H)-one
• 英文别名: phaitanthrin A；6-Acetonyl-6-hydroxy-indolo[2,1-b]quinazolin-12-one；6-hydroxy-6-(2-oxopropyl)indolo[2,1-b]quinazolin-12-one
• CAS: 1033722-02-9
• 化学式: C₁₈H₁₄N₂O₃
• 分子量: 306.321
• InChiKey: CCFVLTFAPUCNHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxy-6-(2-oxopropyl)indolo[2,1-b]quinazolin-12(6H)-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以50%的产率得到6-hydroxy-6-(2-hydrazinylidenepropyl)indolo[2,1-b]quinazolin-12-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of tryptanthrin adducts with ketones

  摘要：

  Reactions of tryptanthrin with acetone, cyclopentanone, hexan-2-one, 4-methylpentan-2-one, 4-hydroxy-4-methylpentan-2-one, cyclohexanone, and butan-2-one in the presence of potassium carbonate afforded racemic phaitanthrin A and other addition products to the ketone group of tryptanthrin with high yields. Thermal dissociation, some chemical transformations, and antimicrobial activity of some adducts were studied, and inhibitory effect against gram-positive bacteria was found for particular derivatives.

  DOI：

  10.1134/s1070428017030174
• 作为产物：
  描述：

  靛红酸酐 在 过氧化脲素 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 生成 6-hydroxy-6-(2-oxopropyl)indolo[2,1-b]quinazolin-12(6H)-one
  参考文献：
  名称：

  One-pot synthesis of tryptanthrin by the Dakin oxidation of indole-3-carbaldehyde

  摘要：

  DOI：

  10.1016/j.tetlet.2014.07.113

文献信息

• Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products
  作者：Subrata Sahoo、Shantanu Pal

  DOI：10.1021/acs.joc.1c02343

  日期：2021.12.17

  A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile

  首次通过铜催化的腈形成、水解和还原在一个锅中揭示了一种从 2-硝基苯甲醛构建喹唑啉酮的新型、高效和原子经济的方法。在该反应中，尿素用作生成腈的氮源，水合肼用于硝基的还原和腈的水解，大气中的氧气用作唯一的氧化剂。该方法描绘了具有良好官能团耐受性的宽底物范围。此外，该方法还用于合成裂殖菌素、色胺菊酯、phaitanthrin-A、phaitanthrin-B和8 H-喹唑啉[4,3 - b ]quinazolin-8-one。
• Isolation, Structure Elucidation, and Synthesis of Cytotoxic Tryptanthrin Analogues from <i>Phaius mishmensis</i>
  作者：Chen-Wei Jao、Wei-Chih Lin、Yao-Ting Wu、Pei-Lin Wu

  DOI：10.1021/np800064w

  日期：2008.7.1

  Bioassay-guided chromatographic separation of the cytotoxic MeOH extract of Phaius mishmensis led to the isolation of two known and six new indoloquinazolinones, phaitanthrins A-E (1-5) and methylisatoid (6). The structures of the new compounds were elucidated by spectroscopic analysis. Phaitanthrin A (1) and tryptanthrin (7) showed moderate cytotoxicity against MCF-7, NCI-H460, and SF-268 cell lines

  生物测定引导的色谱法对米氏海葵的细胞毒性甲醇提取物进行了色谱分离，从而分离出了两种已知的和六种新的吲哚并喹唑啉酮类，泛坦霉素AE（1-5）和甲基isatoid（6）。通过光谱分析阐明了新化合物的结构。Phaitanthrin A（1）和tryptanthrin（7）对MCF-7，NCI-H460和SF-268细胞系显示中等程度的细胞毒性。制备一系列色胺酮的酮加合物，并初步测试了其体外抗MCF-7，NCI-H460和SF-268人癌细胞系的抗癌活性。3-戊酮加合物13显示出类似于色胺酮的活性。
• Switching of Enantioselectivity in the Cu-Catalyzed Asymmetric Decarboxylative Aldol Reaction of Tryptanthrin with <i>β-</i>Keto Acids: An Unexpected Counteranion Effect
  作者：Fang-Fang Feng、Xue-Qi Wang、Long Sun、Chi Wai Cheung、Jing Nie、Jun-An Ma

  DOI：10.1021/acs.orglett.1c01315

  日期：2021.6.4

  Cu-bisoxazoline-catalyzed enantioselective decarboxylative aldol reaction of tryptanthrin with aryl-substituted β-keto acids is developed, providing a straightforward approach to deliver a series of phaitanthrin A analogues. Both enantiomers of the products can be obtained with good to high enantioselectivity in the presence of a single chiral ligand by simply changing the copper salts. Based on the

  开发了 Cu-双恶唑啉催化的色氨酸与芳基取代的β-酮酸的对映选择性脱羧醛醇反应，提供了一种直接的方法来提供一系列的苯菊酯 A 类似物。在单一手性配体存在下，通过简单地改变铜盐，可以以良好到高的对映选择性获得产物的两种对映异构体。基于手性 Cu(II)-双恶唑啉配合物的 X 射线晶体学分析，提出了初步的立体化学模型，以解释观察到的反阴离子诱导的对映选择性转换。
• <i>N</i>-Carboxyanhydrides directly from amino acids and carbon dioxide and their tandem reactions to therapeutic alkaloids
  作者：Thi V. Tran、Yi Shen、Hieu D. Nguyen、Shijie Deng、Hootan Roshandel、Mason M. Cooper、Jose R. Watson、Jeffery A. Byers、Paula L. Diaconescu、Loi H. Do

  DOI：10.1039/d2gc03507c

  日期：——

  versatile N-carboxyanhydrides (NCAs) directly from amino acids and CO2 using n-propylphosphonic anhydride. Most of the NCAs were isolated with >95% purity after simple workup, avoiding the need for tedious purification procedures typically required using conventional methods. Because the reagents and conditions employed are mild, tandem reactions with moisture-sensitive NCAs were carried out to transform

  我们报告了使用正丙基膦酸酐直接从氨基酸和 CO 2制备综合通用的N-羧基酸酐 (NCA) 。大多数 NCA 在简单的后处理后以 > 95% 的纯度被分离出来，避免了使用传统方法通常需要的繁琐纯化程序的需要。由于所使用的试剂和条件温和，因此与对水分敏感的 NCA 进行串联反应，将它们在一锅中转化为药用生物碱色胺菊酯和 Phaitanthrin A。定性分析表明，我们的 NCA 合成方法比直接或间接使用剧毒气体光气的传统方法更环保。
• 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。