N-(N',N'-dimethylaminoethyl)benzo[k, l]thioxanthene-3,4-dicarboximide | 710324-89-3

• 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: N-(N',N'-dimethylaminoethyl)benzo[k, l]thioxanthene-3,4-dicarboximide
• 英文别名: N-(N',N'-dimethylaminoethyl)benzo[k,l]thioxanthene-3,4-dicarboximide；14-[2-(Dimethylamino)ethyl]-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: 710324-89-3
• 化学式: C₂₂H₁₈N₂O₂S
• 分子量: 374.463
• InChiKey: BGKVLOZDBCATTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(N',N'-dimethylaminoethyl)benzo[k, l]thioxanthene-3,4-dicarboximide 在 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以78%的产率得到C₂₂H₁₈N₂O₃S
  参考文献：
  名称：

  Novel aliphatic N-oxide of naphthalimides as fluorescent markers for hypoxic cells in solid tumor

  摘要：

  A series of novel aliphatic N-oxide of naphthalimides (A1-A5) were designed and prepared. The N-O group was firstly introduced into the amine side chain tailed to planar naphthalimide chromophore as hypoxic bioreductive marker. Fluorescence image analysis showed that the compounds could be used as potential markers for hypoxic cells (V79) in vitro especially for A1 with 17 times hypoxic-oxic fluorescence differential, which was probably due to the bis-bioreduction mechanism. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.040
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 盐酸 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成 N-(N',N'-dimethylaminoethyl)benzo[k, l]thioxanthene-3,4-dicarboximide
  参考文献：
  名称：

  Thio-heterocylic naphthalimides with aminoalkyl side chains: novel alternative tools for photodegradation of genomic DNA without impairment on bioactivities of proteins

  摘要：

  Thio-heterocylic naphthalimides (R1-R5) were designed, synthesized and evaluated as nonmetallic and long-wavelength photocleavers. Some of them showed highly efficient abilities in the degradation of plasmid and genomic DNA under the mild conditions without obvious impairment on the proteins' bioactivities, when compared with frequently applied nucleic acids removal reagents or precipitants. Their differences in photodegradation selectivity to DNA rather than proteins were dependent on their photodamage mechanisms and binding modes with bio-macromolecules. When maize genomic DNA was used as substrate, 2.38 x 10(-4) M of R5 exhibited the nuclease activity of 8 Unit DNase 1, R5 has some characteristic as a typical catalyst as no consumption after two cycles of the photodegradation for DNA. The experiments of enzymatic activity assay and immunology activity analysis showed that R5 was safe to proteins, suggesting its potential in the removal of transgenic material during the preparation of bioactive proteins or enzyme preparations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.012

文献信息

• SULFUR-CONTAINING NAPHTHOYLIMIDE DERIVATIVES
  申请人：East China University of Science and Technology

  公开号：EP1626050B1

  公开（公告）日：2009-12-02
• Highly-efficient DNA photocleavers with long wavelength absorptions: thio-heterocyclic fused naphthalimides containing aminoalkyl side chains
  作者：Xuhong Qian、Yonggang Li、Yufang Xu、Yan Liu、Baoyuan Qu

  DOI：10.1016/j.bmcl.2004.02.059

  日期：2004.5

  Thio-heterocyclic fused naphthalimides with aminoalkyl side chains were designed, synthesized and evaluated. These compounds have long wavelength absorptions and binding affinities to Calf thymus DNA. They could photodamage supercoiled pBR322 DNA from form I (closed) to II (nicked) at a concentration as low as 0.5 muM and to form III (linear) at a concentration of 50 muM. A possible mechanism of superoxide anion was provided. (C) 2004 Elsevier Ltd. All rights reserved.
• Novel N-oxide of naphthalimides as prodrug leads against hypoxic solid tumor: Synthesis and biological evaluation
  作者：Hong Yin、Yufang Xu、Xuhong Qian、Yuanli Li、Jianwen Liu

  DOI：10.1016/j.bmcl.2007.02.015

  日期：2007.4

  Novel tertiary amine N-oxides of naphthalimides were designed and synthesized as potential anticancer agents against hypoxic solid tumors. Although their ctDNA-binding affinities and cytotoxic activities against usual tumor cell lines were lower than those of corresponding amines, the N-oxides All and A4 showed hypoxia preference activities against A375 cells in vitro and might be used as interesting candidates of prodrug leads in hypoxic tumor cells. (c) 2007 Elsevier 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