4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione | 1030618-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione
• 英文别名: 4,11-dimethoxynaphtho[2,3-f][1]benzothiole-5,10-dione
• CAS: 1030618-81-5
• 化学式: C₁₈H₁₂O₄S
• 分子量: 324.357
• InChiKey: YFFVYDCWNFWQKI-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C(Solv: nitrobenzene (98-95-3))
• 沸点：
  552.0±50.0 °C(Predicted)
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione 、 羟乙基乙二胺 以56%的产率得到4,11-bis[{2-[(2-hydroxyethyl)amino]ethyl}amino]anthra[2,3-b]thiophene-5,10-dione
  参考文献：
  名称：

  Synthesis and cytotoxic properties of 4,11-bis[(aminoethyl)amino]anthra[2,3-b]thiophene-5,10-diones, novel analogues of antitumor anthracene-9,10-diones

  摘要：

  We developed the synthesis of a series of thiophene-fused tetracyclic analogues of the antitumor drug ametantrone. The reactions included nucleophilic substitution of methoxy groups in 4,11-dimethoxyanthra[2,3-b] thiophene-5,10-diones with ethylenediamines, producing the derivatives of 4,11-diaminoanthra[2,3-b] thiophene-5,10-dione in good yields. Several compounds showed marked antiproliferative potency against doxorubicin-selected, P-glycoprotein-expressing tumor cells and p53 (-/-) cells. The cytotoxicity of some novel compounds for P-glycoprotein-positive cells is highly dependent on N-substituent at the terminal amino group of ethylenediamine moiety. The cytotoxic potency of selected compounds correlated with their ability to attenuate the functions of topoisomerase I and telomerase, strongly suggesting that these enzymes are the major targets of antitumor activity of anthra[2,3-b] thiophene-5,10-dione derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.047
• 作为产物：
  描述：

  4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylic acid 在 copper chromite 作用下， 以 喹啉 为溶剂， 反应 0.5h， 以42%的产率得到4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione
  参考文献：
  名称：

  Heterocyclic analogs of 5,12-naphthacenequinone 6. Synthesis of 4,11-dimethoxy derivatives of anthra-[2,3-b]thiophene-5,10-dione and anthra[2,3-d]isothiazole-5,10-dione

  摘要：

  DOI：

  10.1007/s10593-007-0063-4

文献信息

• Synthesis of thiopheno-quinizarine derivatives
  作者：Yu. B. Sinkevich、A. E. Shchekotikhin、Yu. N. Luzikov、V. N. Buyanov、L. V. Kovalenko

  DOI：10.1007/s10593-007-0191-x

  日期：2007.10