1-chloro-7-methoxy-9H-thioxanthen-9-one | 86456-01-1

• 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-7-methoxy-9H-thioxanthen-9-one
• 英文别名: 1-chloro-7-methoxy-thioxanthen-9-one；1-Chloro-7-methoxythioxanthen-9-one
• CAS: 86456-01-1
• 化学式: C₁₄H₉ClO₂S
• 分子量: 276.743
• InChiKey: FROPPTMDIBNXLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C(Solv: methanol (67-56-1))
• 沸点：
  459.8±45.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-chloro-7-methoxy-9H-thioxanthen-9-one 在 sodium hydroxide 、 3-Cl-C₁₃H₆SO(OCH₃) 、 三氯氧磷 作用下， 以 吡啶 、 甲醇 、 甲酸 、 水 为溶剂， 生成 (2-(Diethylamino)ethy]-9-methoxy-2H-[1]-benzothiopyrano[4,3,2-cd]indazole-5-methanamine
  参考文献：
  名称：

  Cyclic variations of SR 233377 (WIN 33377) and effects on antitumor activity

  摘要：

  Novel derivatives of SR 233377 (1, WIN 33377) where a pyrazolo ring fusion has been incorporated at the 1- and 9-positions of the thioxanthone ring displayed outstanding in vivo efficacy against the murine solid tumor Pane 03 (T/C values of 0% with log cell kill greater than or equal to 2.0). No relationship between structure and Pane 03 activity was observed because all analogues studied were highly active. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00230-2
• 作为产物：
  描述：

  间氯溴苯 在 PPA 、 铜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 1-chloro-7-methoxy-9H-thioxanthen-9-one
  参考文献：
  名称：

  Analogs of hycanthone and lucanthone as antitumor agents

  摘要：

  Hycanthone analogues (5 and 6) containing 7-substituted hydroxyl groups were prepared and evaluated as antitumor agents. These compounds were significantly more active than the corresponding unsubstituted derivatives. The 7-hydroxylated 4-(hydroxymethyl)-9H-xanthen-9-ones, 11 and 12, were also active antitumor agents. However, the 7-hydroxy-9H-xanthen-9-one counterparts of the 7-hydroxylucanthones were totally devoid of antitumor activity. Results obtained thus far are consistent with the hypothesis that 4-hydroxymethyl substituents in the 9H-xanthen-9-one and 9H-thioxanthen-9-one series are required for antitumor activity.

  DOI：

  10.1021/jm00363a007

文献信息

• The preparation, antischistosomal and antitumor activity of hycanthone and some of its congeners. Evidence for the mode of action of hycanthone
  作者：Sydney Archer、Livia Pica-Mattoccia、Donato Cioli、Ahmad Seyed-Mozaffari、Abdel Hadi Zayed

  DOI：10.1021/jm00396a040

  日期：1988.1

  The synthesis of a series of esters of hycanthone (HC) and 7-hydroxyhycanthone, their antitumor activity, and their antischistosomal effects on HC-sensitive and HC-resistant schistosomes are reported. Binding studies using tritium-labeled HC and hycanthone N-methylcarbamate (HNMC) with calf thymus DNA provided evidence that HNMC but not HC alkylated the DNA. Tritiated HNMC also bound to the DNA of

  报道了一系列庚烷酮和7-羟基庚酮的酯的合成，它们的抗肿瘤活性以及它们对HC敏感和HC抵抗性血吸虫的抗血吸虫作用。使用tri标记的HC和庚酮N-甲基氨基甲酸酯（HNMC）与小牛胸腺DNA的结合研究提供了证据，表明HNMC而非HC使DNA烷基化。ti化的HNMC还与暴露于药物的完整HeLa细胞的DNA结合，而在相同条件下，极少的tri化的HC与DNA结合。如方案一所示，先前提出的解释HC的抗血吸虫作用的机制，即药物酯化然后DNA烷基化，也适用于药物的抗肿瘤作用。
• Thioxanthenone antitumor agents
  申请人：Sanofi-Aventis

  公开号：EP1197491B1

  公开（公告）日：2004-12-29
• An Improved Synthetic Method of 1-Chloro-7-methoxy-9<i>H</i>-thioxanthen-9-one
  作者：Hua-Zhong He、Chul-Hoon Kwon

  DOI：10.1081/scc-120021832

  日期：2003.1.8

  1-Chloro-7-methoxy-9H-thioxanthen-9-one (3) was prepared via cyclization of 2-chloro-6-(4-methoxyphenylthio)-benzonitrile (1) in a one pot, two step reaction with improved yield (60%) over the previous literature report.
• J. Med. Chem. 1998, 41, 3645-3654
  作者：

  DOI：——

  日期：——
• Bioorg. Med. Chem. Lett. 1994, 4, 609-614
  作者：

  DOI：——

  日期：——