14-(3-Methylbut-2-enyl)-8-thia-14-azapentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(19),2,4,6,9,11,16(20),17-octaene-13,15-dione | 474319-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 14-(3-Methylbut-2-enyl)-8-thia-14-azapentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(19),2,4,6,9,11,16(20),17-octaene-13,15-dione
• CAS: 474319-57-8
• 化学式: C₂₃H₁₇NO₂S
• 分子量: 371.459
• InChiKey: WMNKRGXQEDFJFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  14-(3-Methylbut-2-enyl)-8-thia-14-azapentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(19),2,4,6,9,11,16(20),17-octaene-13,15-dione 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以30%的产率得到2-(2-Hydroperoxy-3-methyl-but-3-enyl)-6-thia-2-aza-benzo[def]chrysene-1,3-dione
  参考文献：
  名称：

  Novel naphthalimide hydroperoxide photonucleases: The role of thiocyclic-Fused area and the difference in spectra, photochemistry and photobiological activity

  摘要：

  Novel five- and six-membered thiocyclic-fused naphthalimide hydroperoxides (7, 8) as photonucleases were designed, synthesized via unusual isomerization in Pschorr cyclization and photooxygenation. The five-membered 7 was able to induce single-strand nicks in duplex DNA pH independently (7.0-8.5) at 0.5 muM under 366 nm, while the six-membered 8 could photonick the duplex DNA pH dependently (7.0-8.5) at 5 muM under 450 nm and showed 'time-controlled' photo-bioactivity. Their thiocycles and the angular conjugated plane have contributions to their binding affinity with DNA and photocleaving efficiency. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.026
• 作为产物：
  描述：

  3-nitro-4-phenylthio-1,8-naphthalic anhydride 在 盐酸 、 硫酸 、 溶剂黄146 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 14-(3-Methylbut-2-enyl)-8-thia-14-azapentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(19),2,4,6,9,11,16(20),17-octaene-13,15-dione
  参考文献：
  名称：

  Novel naphthalimide hydroperoxide photonucleases: The role of thiocyclic-Fused area and the difference in spectra, photochemistry and photobiological activity

  摘要：

  Novel five- and six-membered thiocyclic-fused naphthalimide hydroperoxides (7, 8) as photonucleases were designed, synthesized via unusual isomerization in Pschorr cyclization and photooxygenation. The five-membered 7 was able to induce single-strand nicks in duplex DNA pH independently (7.0-8.5) at 0.5 muM under 366 nm, while the six-membered 8 could photonick the duplex DNA pH dependently (7.0-8.5) at 5 muM under 450 nm and showed 'time-controlled' photo-bioactivity. Their thiocycles and the angular conjugated plane have contributions to their binding affinity with DNA and photocleaving efficiency. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.026

文献信息

• Synthesis and properties of benzothioxanthene dicarboximide hydroperoxide: an efficient ‘time-resolved’ DNA photocleaver with long-wavelength
  作者：Xuhong Qian、Ping Mao、Wei Yao、Xiangfeng Guo

  DOI：10.1016/s0040-4039(02)00442-2

  日期：2002.4

  A novel hydroperoxide of benzothioxanthene dicarboximide B4 was synthesized through naphthyl radical-induced aromatic 1.5-hydrogen transfer in all unusual Pschorr cyclization and photooxygenation. It vas evaluated as all excellent 'time-resolved' DNA photocleaver with long-wavelength absorption, which can photonick the duplex DNA at a micromolar concentration of 5 muM upon irradiation at 450 nm. (C) 2002 Published by Elsevier Science Ltd.