3-(4-hydroxyphenyl)-5-(2-methylaminoethyl)-1H,7H-pyrrolo[3,2-f]indole-4,8-dione trifluoroacetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(4-hydroxyphenyl)-5-(2-methylaminoethyl)-1H,7H-pyrrolo[3,2-f]indole-4,8-dione trifluoroacetate
• 英文别名: zyzzyanone B；zyzzyanone B trifluoroacetate；3-(4-Hydroxyphenyl)-5-[2-(methylamino)ethyl]-1,7-dihydropyrrolo[3,2-f]indole-4,8-dione;2,2,2-trifluoroacetic acid
• 化学式: C₂HF₃O₂*C₁₉H₁₇N₃O₃
• 分子量: 449.386
• InChiKey: SYDIRQAMIHUNRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-{2-[7-benzyl-5-(4-benzyloxyphenyl)-4,8-dioxo-1-tosyl-1,4,7,8-tetrahydropyrrolo[3,2-f]indol-3-yl]ethyl}-N-methylcarbamic acid tert-butyl ester 在 sodium azide 、 甲酸铵 、 钯 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3-(4-hydroxyphenyl)-5-(2-methylaminoethyl)-1H,7H-pyrrolo[3,2-f]indole-4,8-dione trifluoroacetate
  参考文献：
  名称：

  Total synthesis of zyzzyanones A–D

  摘要：

  Zyzzyanones A-D is a group of biologically active marine alkaloids isolated from Australian marine sponge Zyzzya fuliginosa. They contain a unique bispyrroloquinone ring system as the core structure. The first total synthesis of all four zyzzyanones is described here. The synthesis of these alkaloids started from a previously known 6-benzylamino indole-4,7-quinone derivative and involves 6-7 steps. The key step in the synthesis involves the construction of a pyrrole ring in one step using a Mn(OAc)(3) mediated oxidative free radical cyclization reaction of a 6-benzylamino indole-4,7-quinone derivative with 4-benzyloxyphenyl acetaldehyde diethyl acetal in CH3CN. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.052

文献信息

• Zyzzyanones B−D, Dipyrroloquinones from the Marine Sponge <i>Zyzzya </i><i>f</i><i>uliginosa</i>
  作者：Natalia K. Utkina、Aleksandra E. Makarchenko、Vladimir A. Denisenko

  DOI：10.1021/np050154y

  日期：2005.9.1

  Zyzzyanones B, C, and D (2-4), three new dipyrroloquinones with a pyrrolo[3,2-f]indole-4,8(1H,7H)-dione skeleton, have been isolated from the Australian marine sponge Zyzzya fuliginosa. The known zyzzyanone A, makaluvamines C, E, G, H, and L, damirones A and B, 3,7-dimethylguanine, and 4-hydroxybenzoic acid were also isolated. The structures of the new compounds 2-4 were established by extensive NMR spectroscopic data. Compounds 2-4 showed moderate cytotoxic activity against mouse Ehrlich carcinoma cells (IC50 25 mu g/mL).
• Total synthesis of zyzzyanones A–D
  作者：Dwayaja H. Nadkarni、Srinivasan Murugesan、Sadanandan E. Velu

  DOI：10.1016/j.tet.2013.03.052

  日期：2013.5

  Zyzzyanones A-D is a group of biologically active marine alkaloids isolated from Australian marine sponge Zyzzya fuliginosa. They contain a unique bispyrroloquinone ring system as the core structure. The first total synthesis of all four zyzzyanones is described here. The synthesis of these alkaloids started from a previously known 6-benzylamino indole-4,7-quinone derivative and involves 6-7 steps. The key step in the synthesis involves the construction of a pyrrole ring in one step using a Mn(OAc)(3) mediated oxidative free radical cyclization reaction of a 6-benzylamino indole-4,7-quinone derivative with 4-benzyloxyphenyl acetaldehyde diethyl acetal in CH3CN. (C) 2013 Elsevier Ltd. All rights reserved.