4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylic acid | 1030618-80-4

• 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-2-carboxylic acid
• 英文别名: 4,11-dimethoxy-5,10-dioxonaphtho[2,3-f][1]benzothiole-2-carboxylic acid
• CAS: 1030618-80-4
• 化学式: C₁₉H₁₂O₆S
• 分子量: 368.367
• InChiKey: FLGSBRBGQJFQAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  methyl 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylate 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.17h， 以94%的产率得到4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylic acid
  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

• Thiophene-2-carboxamide derivatives of anthraquinone: A new potent antitumor chemotype
  作者：Yulia L. Volodina、Alexander S. Tikhomirov、Lyubov G. Dezhenkova、Alla A. Ramonova、Anastasia V. Kononova、Daria V. Andreeva、Dmitry N. Kaluzhny、Dominique Schols、Mikhail M. Moisenovich、Andrey E. Shchekotikhin、Alexander A. Shtil

  DOI：10.1016/j.ejmech.2021.113521

  日期：2021.10

  heteroarene-fused anthraquinones, we herein demonstrate that derivative of anthra[2,3-b]thiophene-2-carboxamide, (compound 8) is highly potent against a panel of human tumor cell lines and their drug resistant variants. Treatment with submicromolar or low micromolar concentrations of 8 for only 30 min was sufficient to trigger lethal damage of K562 chronic myelogenous leukemia cells. Compound 8 (2.5 μM, 3–6 h)

  蒽醌支架长期以来一直被认为是有效抗肿瘤药物的来源。特别是，该支架中侧链的各种化学修饰产生了对野生型肿瘤细胞有效的化合物，它们的对应物具有改变药物反应的分子决定因素，以及体内环境。进一步探索抗癌杂芳烃稠合蒽醌的化学型，我们在此证明蒽[2,3 - b ]噻吩-2-甲酰胺衍生物（化合物8）对一组人类肿瘤细胞系及其耐药性非常有效变种。用亚微摩尔或低微摩尔浓度8 处理仅 30 分钟就足以引发 K562 慢性粒细胞白血病细胞的致死性损伤。化合物8（2.5 μM，3-6 小时）诱导了细胞凋亡，这取决于半胱天冬酶 3 和 9 的伴随激活、聚（ADP-核糖）聚合酶的裂解、膜联蛋白 V/碘化丙啶双染色细胞的增加、DNA 片段化(subG1 分数) 和线粒体膜电位的降低。在无细胞系统中，既不能检测到与双链 DNA 的显着相互作用，也不能检测到 DNA 依赖性酶拓扑异构酶 1 by 8 的强烈抑制。激光扫描共聚焦显微镜显示，大约有8加入细胞后
• 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
  作者：Andrey E. Shchekotikhin、Valeria A. Glazunova、Lyubov G. Dezhenkova、Yuri N. Luzikov、Yuri B. Sinkevich、Leonid V. Kovalenko、Vladimir N. Buyanov、Jan Balzarini、Fong-Chun Huang、Jing-Jer Lin、Hsu-Shan Huang、Alexander A. Shtil、Maria N. Preobrazhenskaya

  DOI：10.1016/j.bmc.2009.01.047

  日期：2009.3

  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.