(4S)-4-(3-indolylmethyl)-1,2,3,4-tetrahydro-5H-pyrazino[2,1-b]quinazoline-3,6-dione | 264602-12-2

• 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: (4S)-4-(3-indolylmethyl)-1,2,3,4-tetrahydro-5H-pyrazino[2,1-b]quinazoline-3,6-dione
• 英文别名: (4S)-4-((indol-2-yl)methyl)-1,2-dihydro-4H-pyrazino[2,1-b]quinazoline-3,6-dione；(S)-4-(1H-indol-3-ylmethyl)-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione；dhydrofumiquinazoline；(+)-glyantrypine；glyantrypine；(4S)-4-(1H-indol-3-ylmethyl)-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
• CAS: 264602-12-2
• 化学式: C₂₀H₁₆N₄O₂
• 分子量: 344.373
• InChiKey: YFNRNQBGKNOAPT-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (4S)-4-(3-indolylmethyl)-1,2,3,4-tetrahydro-5H-pyrazino[2,1-b]quinazoline-3,6-dione 在 吡啶 作用下， 反应 19.0h， 以67%的产率得到N,N-diacetylglyantrypine
  参考文献：
  名称：

  Synthesis of (−)-lapatin B

  摘要：

  The synthesis of (-)-lapatin B (1) has been achieved from L-tryptophan. The key reactions involve oxidative cyclization of N,N-diacetylglyantrypine (8) using PhI(OH)(OTs), and an indole-to-oxindole transformation in the penultimate step. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.089
• 作为产物：
  描述：

  N-苄氧羰基-L-色氨酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium hydroxide 、 三丁基膦 、 氢气 、 一水合肼 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 63.0h， 生成 (4S)-4-(3-indolylmethyl)-1,2,3,4-tetrahydro-5H-pyrazino[2,1-b]quinazoline-3,6-dione
  参考文献：
  名称：

  A New Route toward 4-Substituted Pyrazino[2,1-b]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine

  摘要：

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.

  DOI：

  10.1021/jo991626e

文献信息

• Enzymatic Processing of Fumiquinazoline F: A Tandem Oxidative-Acylation Strategy for the Generation of Multicyclic Scaffolds in Fungal Indole Alkaloid Biosynthesis
  作者：Brian D. Ames、Xinyu Liu、Christopher T. Walsh

  DOI：10.1021/bi1012029

  日期：2010.10.5

  Af12060, are necessary and sufficient to convert FQF to FQA. Af12060 oxidizes the 2′,3′-double bond of the indole side chain of FQF, and the three-domain NRPS Af12050 activates l-Ala as the adenylate, installs it as the pantetheinyl thioester on its carrier protein domain, and acylates the oxidized indole for subsequent intramolecular cyclization to create the 6-5-5 imidazolindolone of FQA. This work provides

  烟曲霉Af293 是喹唑啉天然产物的已知生产者，包括抗肿瘤化合物文喹唑啉，其中最简单的成员是文喹唑啉 F (FQF)，具有衍生自邻氨基苯甲酸、色氨酸和丙氨酸的 6-6-6 三环核心。FQF 是文喹唑啉 A (FQA) 的生物前体，其中吲哚侧链通过附加丙氨酸分子的氧化偶联进行修饰，产生融合的 6-5-5 咪唑吲哚酮。我们最近通过生物信息学方法鉴定了真菌邻氨基苯甲酸激活非核糖体肽合成酶（NRPS）结构域。之前确定的一个结构域是三模块 NRPS Af12080 的一部分，我们预测它负责 FQF 的形成。我们现在表明，两个相邻的烟曲霉ORF（单模块 NRPS Af12050 和黄素蛋白 Af12060）对于将 FQF 转化为 FQA 是必要且充分的。Af12060 氧化 FQF 吲哚侧链的 2',3'-双键，三结构域 NRPS Af12050 激活l -Ala 作为腺苷酸，将其作为泛醇硫酯安装在其
• Three-Component One-Pot Total Syntheses of Glyantrypine, Fumiquinazoline F, and Fiscalin B Promoted by Microwave Irradiation
  作者：Ji-Feng Liu、Ping Ye、Bailin Zhang、Grace Bi、Katie Sargent、Libing Yu、Daniel Yohannes、Carmen M. Baldino

  DOI：10.1021/jo0508043

  日期：2005.8.1

  A microwave-promoted three-component one-pot reaction has been developed to provide access to the core pyrazino[2,1-b]quinazoline-3,6-dione (1) scaffold, which is common to several families of alkaloids with significant biological activities. By adapting this synthetic strategy through the use of selected Boc-amino acids and amino acid esters, we have accomplished highly efficient and concise total syntheses of glyantrypine (2), fumiquinazoline F (3), and fiscalin B (5), achieving overall yields of 55, 39, and 20%, respectively.
• A New Route toward 4-Substituted Pyrazino[2,1-<i>b</i>]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine
  作者：Pilar Cledera、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1021/jo991626e

  日期：2000.3.1

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.
• Synthesis of (−)-lapatin B
  作者：Steven J. Walker、David J. Hart

  DOI：10.1016/j.tetlet.2007.06.089

  日期：2007.8

  The synthesis of (-)-lapatin B (1) has been achieved from L-tryptophan. The key reactions involve oxidative cyclization of N,N-diacetylglyantrypine (8) using PhI(OH)(OTs), and an indole-to-oxindole transformation in the penultimate step. (C) 2007 Elsevier Ltd. All rights reserved.