14-(3-Methylbut-2-enyl)-3-thia-14-azapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1,4,6,8,10,12(20),16,18-octaene-13,15-dione | 312699-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 14-(3-Methylbut-2-enyl)-3-thia-14-azapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1,4,6,8,10,12(20),16,18-octaene-13,15-dione
• CAS: 312699-46-0
• 化学式: C₂₃H₁₇NO₂S
• 分子量: 371.459
• InChiKey: VPBCXVKXKRPFCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 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：
  65.6
• 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)-3-thia-14-azapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1,4,6,8,10,12(20),16,18-octaene-13,15-dione 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 6.5h， 生成 14-(2-Hydroxy-3-methylbut-3-enyl)-3-thia-14-azapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1,4,6,8,10,12(20),16,18-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
• 作为产物：
  描述：

  苯硫酚 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 14-(3-Methylbut-2-enyl)-3-thia-14-azapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1,4,6,8,10,12(20),16,18-octaene-13,15-dione
  参考文献：
  名称：

  Novel and highly efficient DNA photocleavers: hydroperoxides of heterocyclic-fused naphthalimides

  摘要：

  A series of novel hydroperoxides of heterocyclic-fused naphthalimides were designed, synthesized and exhibited excellent DNA photonicking activities. Among these compounds, the benzothiophenonaphthalimide-type reagent proved to be the most efficient, it can induce single-strand nicks in duplex DNA at micromolar concentration upon illumination. The relationship between the molecular structure and cleaving activities was discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01304-6

文献信息

• Novel and highly efficient DNA photocleavers: hydroperoxides of heterocyclic-fused naphthalimides
  作者：Wei Yao、Xuhong Qian、Qingyan Hu

  DOI：10.1016/s0040-4039(00)01304-6

  日期：2000.9

  A series of novel hydroperoxides of heterocyclic-fused naphthalimides were designed, synthesized and exhibited excellent DNA photonicking activities. Among these compounds, the benzothiophenonaphthalimide-type reagent proved to be the most efficient, it can induce single-strand nicks in duplex DNA at micromolar concentration upon illumination. The relationship between the molecular structure and cleaving activities was discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.
• SULFUR-CONTAINING NAPHTHALIMIDE DERIVATIVES
  申请人：Qian Xuhong

  公开号：US20080234287A1

  公开（公告）日：2008-09-25

  The invention discloses novel sulfur-containing naphthalimide derivatives, and the preparation and uses thereof. The conjugated plane of naphthalimide derivatives of the invention is enlarged by incorporating 5- or 6-membered heteroaromatic ring and/or introducing S heteroatom, thus increasing the anti-tumor activity of naphthalimide. The compounds of the invention displays significant inhibiting activities to the proliferation of various tumor cells such as human lung cancer, gastric cancer, liver cancer, leucocythemia and the like. The inhibition of cell proliferation is dose-dependent.
• US7541463B2
  申请人：——

  公开号：US7541463B2

  公开（公告）日：2009-06-02
• Novel naphthalimide hydroperoxide photonucleases: The role of thiocyclic-Fused area and the difference in spectra, photochemistry and photobiological activity
  作者：Yufang Xu、Xuhong Qian、Wei Yao、Ping Mao、Jingnan Cui

  DOI：10.1016/j.bmc.2003.09.026

  日期：2003.12

  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.