12-Methyl-3-oxa-11-thia-13-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),12-hexaene-2,4-dione | 167541-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并噻唑类
• 英文名称: 12-Methyl-3-oxa-11-thia-13-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),12-hexaene-2,4-dione
• 英文别名: 12-methyl-3-oxa-11-thia-13-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),12-hexaene-2,4-dione
• CAS: 167541-85-7
• 化学式: C₁₄H₇NO₃S
• 分子量: 269.28
• InChiKey: IZMDXAZPAUQDDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  12-Methyl-3-oxa-11-thia-13-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),12-hexaene-2,4-dione 、 N-氨乙基哌嗪 以 乙醇 为溶剂， 反应 3.0h， 生成 12-Methyl-3-(2-piperazin-1-ylethyl)-11-thia-3,13-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),12-hexaene-2,4-dione
  参考文献：
  名称：

  Synthesis, antitumor evaluation and DNA photocleaving activity of novel methylthiazonaphthalimides with aminoalkyl side chains

  摘要：

  A series of methylthiazonaphthalimides was synthesized and quantitatively evaluated as efficient DNA intercalators, antitumor agents and DNA photocleavers. A(1) showed both efficient antitumor activities against cell lines of A549 and P388 with IC50 Of 82.8 and 31 nM, respectively. A(3) was the strongest antitumor agent against A549 with the IC50 of 20.8 nM. A(2), the most efficient DNA intercalator, was found to be the strongest DNA photocleaver via superoxide anion. An explanation was given for the disaccord between antitumor and DNA photocleaving activities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.012
• 作为产物：
  描述：

  4-溴-3-硝基-1,8-萘酐 在 sodium disulfide 、 溶剂黄146 作用下， 反应 12.0h， 生成 12-Methyl-3-oxa-11-thia-13-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),12-hexaene-2,4-dione
  参考文献：
  名称：

  Synthesis, antitumor evaluation and DNA photocleaving activity of novel methylthiazonaphthalimides with aminoalkyl side chains

  摘要：

  A series of methylthiazonaphthalimides was synthesized and quantitatively evaluated as efficient DNA intercalators, antitumor agents and DNA photocleavers. A(1) showed both efficient antitumor activities against cell lines of A549 and P388 with IC50 Of 82.8 and 31 nM, respectively. A(3) was the strongest antitumor agent against A549 with the IC50 of 20.8 nM. A(2), the most efficient DNA intercalator, was found to be the strongest DNA photocleaver via superoxide anion. An explanation was given for the disaccord between antitumor and DNA photocleaving activities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.012

文献信息

• BIS-IMIDE POLYCYCLIC AND HETEROCYCLIC CHROMOPHORES USEFUL AS TUMORICIDALS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0705250A1

  公开（公告）日：1996-04-10
• US5416089A
  申请人：——

  公开号：US5416089A

  公开（公告）日：1995-05-16
• US5585382A
  申请人：——

  公开号：US5585382A

  公开（公告）日：1996-12-17
• [EN] BIS-IMIDE POLYCYCLIC AND HETEROCYCLIC CHROMOPHORES USEFUL AS TUMORICIDALS<br/>[FR] CHROMOPHORES BIS-IMIDE POLYCYCLIQUES ET HETEROCYCLIQUES UTILES COMME AGENTS ANTICANCEREUX
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1995000490A1

  公开（公告）日：1995-01-05

  (EN) This invention relates to bis-imide derivatives of tri- and tetraamines of formula (I), pharmaceutical compositions containing them, and methods of using them to treat cancer, particularly solid tumors, in mammals.(FR) Cette invention concerne des dérivés bis-imide de triamines et de tétraamines de la formule (I), des compositions pharmaceutiques les contenant et des méthodes d'utilisation de celles-ci pour traiter le cancer, en particulier les tumeurs solides chez les mammifères.
• Novel thiazonaphthalimides as efficient antitumor and DNA photocleaving agents: Effects of intercalation, side chains, and substituent groups
  作者：Zhigang Li、Qing Yang、Xuhong Qian

  DOI：10.1016/j.bmc.2005.05.006

  日期：2005.8

  A series of novel antitumor and DNA photocleaving agents was designed and synthesized by fusing a (substituted) thiazole ring to the naphthalimide skeletons. C-1, the most active compound against A549. was about 10-fold more cytotoxic than the compound amonafide. A,. the most active compound against P388, was about 6-fold more cylotoxic than amonafide. C-2, the most efficient DNA intercalator, showed the strongest DNA photocleaving activity Via Superoxide anion produced under UV light at 360 nm. (c) 2005 Elsevier Ltd. All rights reserved.