1-chloro-4-hydroxy-9H-thioxanthen-9-one | 59803-22-4

• 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: 1-chloro-4-hydroxy-9H-thioxanthen-9-one
• 英文别名: 1-Chloro-4-hydroxythioxanthone；1-chloro-4-hydroxythioxanthen-9-one
• CAS: 59803-22-4
• 化学式: C₁₃H₇ClO₂S
• 分子量: 262.716
• InChiKey: CHVNGPFOOJHLLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-chloro-4-hydroxy-9H-thioxanthen-9-one 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 40.0h， 生成 1-[2-(Diethylamino)ethylamino]-4-phenylmethoxythioxanthen-9-one
  参考文献：
  名称：

  Ring-hydroxylated analogs of lucanthone as antitumor agents

  摘要：

  A series of ring-alkoxylated and ring-hydroxylated analogues of lucanthone was prepared and tested for antitumor activity. The most biologically interesting members of this group were the 7-hydroxylucanthone derivatives, 50 and 51, which gave T/C values in the NCI P-388 antitumor screen of 188 and 265, respectively. The apparent association constants and delta Tm values for a number of analogue-DNA complexes were determined to ascertain whether there was any quantitative correlation with biological activity. The most that can be said is that intercalation may be a necessary but far from sufficient condition for antitumor activity.

  DOI：

  10.1021/jm00345a006
• 作为产物：
  描述：

  1-氯-4-丙氧基硫杂蒽-9-酮 在 三溴化硼 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到1-chloro-4-hydroxy-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

文献信息

• [EN] NEW PHOTOINITIATORS<br/>[FR] NOUVEAUX PHOTOINITIATEURS
  申请人：SIEGWERK BENELUX SA

  公开号：WO2010124950A1

  公开（公告）日：2010-11-04

  The present invention is related to novel photoinitiators, in particular to photoinitiators comprising amino groups within the molecule.

  这项发明涉及新型光引发剂，特别是包含分子内氨基团的光引发剂。
• Synthesis of new lariat ethers containing polycyclic phenols and heterocyclic aromatic compound on graphite surface via mannich reaction
  作者：H. Sharghi、R. Khalifeh、A. R. Salimi Beni

  DOI：10.1007/bf03245889

  日期：2010.3

  Synthesis of novel lariat ethers containing polycyclic phenols and heterocyclic aromatic compound using graphite via Mannich reaction are herein described. For this purpose N-(methoxymethyl) azacrown ether 4 was synthesized in nearly quantitative yield. The reaction of N-(methoxymethyl) azacrown ether 4 with polycyclic phenols and heterocyclic aromatic compound was performed in 10-20 min in the presence

  本文描述了经由曼尼希反应使用石墨合成包含多环酚和杂环芳族化合物的新型套索状醚。为此目的，以几乎定量的产率合成了N-（甲氧基甲基）氮杂皇冠醚4。的反应ñ - （甲氧基甲基）氮杂冠醚4与多环酚和杂环芳族化合物是在10-20分钟中石墨的存在下进行。用丙酮简单洗涤后，石墨粉最多可重复使用五次。
• Ruthenium-catalyzed C–H activation of thioxanthones
  作者：Danny Wagner、Stefan Bräse

  DOI：10.3762/bjoc.11.49

  日期：——

  Thioxanthones - being readily available in one step from thiosalicylic acid and arenes - were used in ruthenium-catalyzed C-H-activation reaction to produce 1-mono- or 1,8-disubstituted thioxanthones in good to excellent yields. Scope and limitation of this reaction are presented.

  噻吨酮（可通过硫代水杨酸和芳烃一步获得）用于钌催化的 CH 活化反应，以良好至优异的产率生产 1-单取代或 1,8-二取代的噻吨酮。介绍了该反应的范围和局限性。
• NOVEL PHOTOINITIATORS
  申请人：Madsen Niels Joergen

  公开号：US20130296577A1

  公开（公告）日：2013-11-07

  Novel photoinitiators provide for polyurethane formation, in which a photoinitiator moiety and a tertiary amine are incorporated into the photoinitiator structure, and thus the polyurethane polymer.

  新型光引发剂可用于聚氨酯的形成，其中光引发剂基团和三级胺被并入光引发剂结构，从而形成聚氨酯聚合物。
• [EN] POLYMERISABLE PHOTOINITIATORS FOR LED CURABLE COMPOSITIONS<br/>[FR] PHOTOINITIATEURS POLYMÉRISABLES POUR COMPOSITIONS DURCISSABLES PAR LED
  申请人：AGFA GEVAERT

  公开号：WO2012052288A1

  公开（公告）日：2012-04-26

  A polymerisable photoinitiator according to Formula (I): wherein: R1 and R2 are independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkaryl group, a substituted or unsubstituted aryl or heteroaryl group, a halogen, an ether group, a thioether group, an aldehyde group, a ketone group, an ester group, an amide group, an amine and a nitro group; R1 and R2 may represent the necessary atoms to form a five to eight memberering; L represents an n+m-valent linking group comprising 1 to 30 carbon atoms; A represents a radically polymerizable group selected from the group consisting of an acrylate group, a methacrylate group, a styrene group, an acryl amide group a methacryl amide group, a maleate group, a fumarate group, an itaconate group, a vinyl ether group, an allyl ether group, a vinyl ester group and an allyl ester group;and n and m independently represent an integer from 1 to 5. Methods for preparing the polymerisable photoinitiator and radiation curable compositions including the polymerisable photoinitiator are also disclosed.

  根据公式（I）提供的可聚合光引发剂：其中：R1和R2独立地选自包括氢，取代或未取代的烷基，取代或未取代的烯基，取代或未取代的炔基，取代或未取代的芳基烷基，取代或未取代的烷基芳基基，取代或未取代的芳基或杂芳基，卤素，醚基，硫醚基，醛基，酮基，酯基，酰胺基，胺基和硝基的群; R1和R2可以表示形成五到八成员环所必需的原子; L表示1到30个碳原子的n+m价键连接基；A表示选自包括丙烯酸酯基，甲基丙烯酸酯基，苯乙烯基，丙烯酰胺基，甲基丙烯酰胺基，马来酸酯基，富马酸酯基，顺丁烯二酸酯基，乙烯醚基，烯丙醚基，乙烯酸酯基和烯丙酸酯基的自由基聚合基团; n和m独立地表示1到5的整数。还公开了制备可聚合光引发剂和包括可聚合光引发剂的辐射可固化组合物的方法。