verrucine B | 252032-23-8

• 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 B
• 英文别名: (1R,4S)-1,3,4,6-tetrahydro-3,6-dioxo-1-(phenylmethyl)-2H-pyrazino[2,1-b]quinazoline-4-propanamide；3-[(1R,4S)-1-benzyl-3,6-dioxo-2,4-dihydro-1H-pyrazino[2,1-b]quinazolin-4-yl]propanamide
• CAS: 252032-23-8
• 化学式: C₂₁H₂₀N₄O₃
• 分子量: 376.415
• InChiKey: LISCNUCDEMJKLE-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  verrucine B 在 air 作用下， 以 甲醇 、 氘代二甲亚砜 为溶剂， 生成 (1S,4S)-1,3,4,6-tetrahydro-3,6-dioxo-1-hydroxy-1-(phenylmethyl)-2H-pyrazino[2,1-b]quinazoline-4-propanamide
  参考文献：
  名称：

  Total Solid Phase Syntheses of the Quinazoline Alkaloids:  Verrucines A and B and Anacine

  摘要：

  The first total syntheses of verrucines A and B and anacine (revised structure) were accomplished on Sasrin resin. This work confirmed the structure of verrucine A and unambiguously showed verrucine B to be a derivative of D-phenylalanine and L-glutamine, The study also proved that anacine and its epimer are quinazoline alkaloids, not benzodiazepines as originally proposed. 1-Hydroxyverrucine B, derived from air oxidization of verrucine B, was also isolated and characterized.

  DOI：

  10.1021/np010342y
• 作为产物：
  描述：

  N-[(1S)-2-氯-2-氧代-1-(苯甲基)乙基]-氨基甲酸-9H-芴-9-甲酯 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 verrucine B
  参考文献：
  名称：

  Total Solid Phase Syntheses of the Quinazoline Alkaloids:  Verrucines A and B and Anacine

  摘要：

  The first total syntheses of verrucines A and B and anacine (revised structure) were accomplished on Sasrin resin. This work confirmed the structure of verrucine A and unambiguously showed verrucine B to be a derivative of D-phenylalanine and L-glutamine, The study also proved that anacine and its epimer are quinazoline alkaloids, not benzodiazepines as originally proposed. 1-Hydroxyverrucine B, derived from air oxidization of verrucine B, was also isolated and characterized.

  DOI：

  10.1021/np010342y

文献信息

• Verrucine F, a Quinazoline from <i>Penicillium verrucosum</i>
  作者：Su-lin Leong、Johan Schnürer、Anders Broberg

  DOI：10.1021/np800105e

  日期：2008.8.1

  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.