4-Acetyloxy-1-chlorothioxanthone | 147053-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 4-Acetyloxy-1-chlorothioxanthone
• 英文别名: (1-chloro-9-oxothioxanthen-4-yl) acetate
• CAS: 147053-83-6
• 化学式: C₁₅H₉ClO₃S
• 分子量: 304.754
• InChiKey: VRNYBRHUUMHZDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Acetyloxy-1-chlorothioxanthone 、 3,4,5-三甲氧基苯胺 在 copper(I) oxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.83h， 以7%的产率得到4-Hydroxy-1-[(3,4,5-trimethoxyphenyl)amino]-9H-thioxanthen-9-one
  参考文献：
  名称：

  Dual inhibitors of P-glycoprotein and tumor cell growth: (Re)discovering thioxanthones

  摘要：

  For many pathologies, there is a crescent effort to design multiple ligands that interact with a wide variety of targets. 1-Aminated thioxanthone derivatives were synthesized and assayed for their in vitro dual activity as antitumor agents and P-glycoprotein (P-gp) inhibitors. The approach was based on molecular hybridization of a thioxanthone scaffold, present in known antitumor drugs, and an amine, described as an important pharmacophoric feature for P-gp inhibition. A rational approach using homology modeling and docking was used, to select the molecules to be synthesized by conventional or microwave-assisted Ullmann C-N cross-coupling reaction. The obtained aminated thioxanthones were highly effective at inhibiting P-gp and/or causing growth inhibition in a chronic myelogenous leukemia cell line, K562. Six of the aminated thioxanthones had GI(50) values in the 1(562 cell line below 10 mu M and 1-{[2-(diethylamino)ethyl]amino}-4-propoxy-9H-thioxanthen-9-one (37) had a GI(50) concentration (1.90 mu M) 6-fold lower than doxorubicin (11.89 mu M) in the K562Dox cell line. The best P-gp inhibitor found was 1-[2-(1H-benzimidazol-2-yl)ethanamine]-4-propoxy-9H-thioxanthen-9-one (45), which caused an accumulation rate of rhodamine-123 similar to that caused by verapamil in the K562Dox resistant cell line, and a decrease in ATP consumption by P-gp. At a concentration of 10 mu M, compound 45 caused a decrease of 12.5-fold in the GI(50) value of doxorubicin in the K562Dox cell line, being 2-fold more potent than verapamil. From the overall results, the aminated thioxanthones represent a new class of P-gp inhibitors with improved efficacy in sensitizing a resistant P-gp overexpressing cell line (K562Dox) to doxorubicin. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2011.10.004
• 作为产物：
  描述：

  1-氯-4-丙氧基硫杂蒽-9-酮 在 吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 4-Acetyloxy-1-chlorothioxanthone
  参考文献：
  名称：

  Dual inhibitors of P-glycoprotein and tumor cell growth: (Re)discovering thioxanthones

  摘要：

  For many pathologies, there is a crescent effort to design multiple ligands that interact with a wide variety of targets. 1-Aminated thioxanthone derivatives were synthesized and assayed for their in vitro dual activity as antitumor agents and P-glycoprotein (P-gp) inhibitors. The approach was based on molecular hybridization of a thioxanthone scaffold, present in known antitumor drugs, and an amine, described as an important pharmacophoric feature for P-gp inhibition. A rational approach using homology modeling and docking was used, to select the molecules to be synthesized by conventional or microwave-assisted Ullmann C-N cross-coupling reaction. The obtained aminated thioxanthones were highly effective at inhibiting P-gp and/or causing growth inhibition in a chronic myelogenous leukemia cell line, K562. Six of the aminated thioxanthones had GI(50) values in the 1(562 cell line below 10 mu M and 1-{[2-(diethylamino)ethyl]amino}-4-propoxy-9H-thioxanthen-9-one (37) had a GI(50) concentration (1.90 mu M) 6-fold lower than doxorubicin (11.89 mu M) in the K562Dox cell line. The best P-gp inhibitor found was 1-[2-(1H-benzimidazol-2-yl)ethanamine]-4-propoxy-9H-thioxanthen-9-one (45), which caused an accumulation rate of rhodamine-123 similar to that caused by verapamil in the K562Dox resistant cell line, and a decrease in ATP consumption by P-gp. At a concentration of 10 mu M, compound 45 caused a decrease of 12.5-fold in the GI(50) value of doxorubicin in the K562Dox cell line, being 2-fold more potent than verapamil. From the overall results, the aminated thioxanthones represent a new class of P-gp inhibitors with improved efficacy in sensitizing a resistant P-gp overexpressing cell line (K562Dox) to doxorubicin. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2011.10.004

文献信息

• Thioxanthone derivatives
  申请人：International Bio-Synthetics Limited

  公开号：US05414092A1

  公开（公告）日：1995-05-09

  Thioxanthone derivatives of the general formula I ##STR1## wherein R.sup.1 wherein R.sup.1 represents a halogen atom or a C.sub.1-10 alkoxy group, R.sup.2 and R.sup.4 each represent a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.6 alkyl group, X represents oxygen or sulphur, and R.sup.3 represents a C.sub.1 -C.sub.10 alkyl group optionally substituted by a hydroxy group which hydroxy group may be alkylated by an optionally substituted C.sub.1-6 alkyl, C.sub.1-6 alkenyl or a benzyl group or acylated by a C.sub.1-8 alkanoyl or C.sub.1-8 alkenoyl group, a C.sub.1-10 alkenyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.1 -C.sub.8 alkanoyl group, a C.sub.1-8 alkenoyl group, an optionally substituted phenyl group, an optionally substituted benzyl group or an optionally substituted benzoyl group. Process for the preparation of the above thioxanthones, their use as photoinitiators, photopolymerisable compositions containing them, the use of such compositions for the production of photocured surface coating and products on which these photocured compositions have been applied.

  通用公式I的噻吩酮衍生物##STR1##其中R.sup.1代表卤素原子或C.sub.1-10烷氧基团，R.sup.2和R.sup.4各自代表氢原子、卤素原子或C.sub.1-C.sub.6烷基团，X代表氧或硫，R.sup.3代表C.sub.1-C.sub.10烷基团，该烷基团可以选择地被一个羟基取代，而该羟基可能被一个选择性取代的C.sub.1-6烷基、C.sub.1-6烯基或苄基烷基化，或者被一个C.sub.1-8烷酰基或C.sub.1-8烯酰基团酰化，一个C.sub.1-10烯基团，一个C.sub.3-C.sub.6环烷基团，一个C.sub.1-C.sub.8烷酰基团，一个C.sub.1-8烯酰基团，一个可选择取代的苯基团，一个可选择取代的苄基团或一个可选择取代的苯甲酰基团。上述噻吩酮的制备方法，它们作为光引发剂的用途，含有它们的光聚合组合物，以及这些光聚合组合物用于生产光固化表面涂层和应用了这些光固化组合物的产品的用途。
• US5414092A
  申请人：——

  公开号：US5414092A

  公开（公告）日：1995-05-09