verrucine F | 1049778-80-4

• 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: verrucine F
• 英文别名: 3-[(1Z,4S)-1-benzylidene-3,6-dioxo-4H-pyrazino[2,1-b]quinazolin-4-yl]propanamide
• CAS: 1049778-80-4
• 化学式: C₂₁H₁₈N₄O₃
• 分子量: 374.399
• InChiKey: WUEWXBLUBVLZJD-WBILKINKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  verrucine A 在 tris-HCl-buffer 、 β-烟酰胺腺嘌呤二核苷酸 作用下， 以 水 为溶剂， 生成 verrucine F
  参考文献：
  名称：

  Verrucine F, a Quinazoline from Penicillium verrucosum

  摘要：

  Verrucine F (3), a quinazoline similar to verrucines A (1) and B (2), contains one anthranilic acid residue, one L-glutamine residue, and one alpha,beta-unsaturated phenylalanine residue, as determined by NMR, MS, and chemical methods. Compounds I and 3, but not 2, were produced by Penicillium verrucosum J255 and eight additional P. verrucosum strains. Verrucines were typically more concentrated in the inner (older) parts of the colony, and 3 peaked 4-8 days after 1, but at 10-fold lower concentrations (similar to 200 mu g/g). Verrucine F (3) formed spontaneously from 1 in buffered water solutions. probably by oxidation at C-1 followed by water elimination.

  DOI：

  10.1021/np800105e

文献信息

• Total Synthesis of Cyclotripeptidic Natural Products Anacine, Aurantiomide C, Polonimides A and C, and Verrucine F
  作者：Guanghui Han、Wei Zhang、Emmanuelle Acs、Alexis Paquin、Quentin Ronzon、Nicolas Casaretto、Bastien Nay

  DOI：10.1021/acs.orglett.4c00658

  日期：2024.4.5

  The total synthesis of cyclotripeptidic natural products possessing a central piperazino[2,1-b]quinazolin-3,6-dione core is described through an original strategy involving the pivotal cyclocondensation of an electrophilic homoserine lactone intermediate. The alkylidene group was spontaneously installed by autoxidation during the cyclocondensation process, while the propionamide side chain was introduced

  通过涉及亲电子高丝氨酸内酯中间体的关键环缩合的原始策略描述了具有中心哌嗪[2,1- b ]喹唑啉-3,6-二酮核心的环三肽天然产物的全合成。亚烷基是在环缩合过程中通过自氧化自发安装的，而丙酰胺侧链是通过溴乙基中间体的镍催化氨基羰基化引入的。对于这种高度功能化的中间体来说，最后的反应是前所未有的。最后，我们探索了天然产物的结构修饰和相互转化。总体而言，这项工作产生了 anacine、aurantiomide C、polonimides A 和 C 以及 verrucine F。