1-<<2-(dimethylamino)ethyl>amino>-7-hydroxy-9-oxo-9H-thioxanthene-4-carboxaldehyde | 86456-11-3

• 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-<<2-(dimethylamino)ethyl>amino>-7-hydroxy-9-oxo-9H-thioxanthene-4-carboxaldehyde
• 英文别名: 1-<<2-(dimethylamino)ethyl>amino>-9-oxo-7-hydroxy-9H-thioxanthene-4-carboxaldehyde；1-[[2-(Dimethylamino)ethyl]amino]-7-hydroxy-9-oxo-9H-thioxanthene-4-carboxaldehyde；1-{[2-(dimethylamino)ethyl]amino}-7-hydroxy-9-oxo-9H-thioxanthene-4-carboxaldehyde；1-[2-(Dimethylamino)ethylamino]-7-hydroxy-9-oxothioxanthene-4-carbaldehyde
• CAS: 86456-11-3
• 化学式: C₁₈H₁₈N₂O₃S
• 分子量: 342.419
• InChiKey: NXXCKLQOROCGHB-UHFFFAOYSA-N

物化性质

• 熔点：
  222-223 °C(Solv: methanol (67-56-1))
• 沸点：
  587.4±50.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-<<2-(dimethylamino)ethyl>amino>-7-hydroxy-9-oxo-9H-thioxanthene-4-carboxaldehyde 在 咪唑 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 1-<<2-(dimethylamino)ethyl>amino>-7-<(tert-butyldiphenylsilyl)oxy>-4-(hydroxymethyl)-9H-thioxanthen-9-one
  参考文献：
  名称：

  庚酮及其某些同类物的制备及其抗血吸虫和抗肿瘤活性。庚酮作用方式的证据。

  摘要：

  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。

  DOI：

  10.1021/jm00396a040
• 作为产物：
  描述：

  间氯溴苯 在 manganese(IV) oxide 、 PPA 、 吡啶盐酸盐 、 铜 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.5h， 生成 1-<<2-(dimethylamino)ethyl>amino>-7-hydroxy-9-oxo-9H-thioxanthene-4-carboxaldehyde
  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

• ARCHER, S.
  作者：ARCHER, S.

  DOI：——

  日期：——
• ARCHER, SYDNEY;PICA-MATTOCCIA, LIVIA;CIOLI, DONATO;SEYED-MOZAFFARI, AHMAD+, J. MED. CHEM., 31,(1988) N 1, 254-260
  作者：ARCHER, SYDNEY、PICA-MATTOCCIA, LIVIA、CIOLI, DONATO、SEYED-MOZAFFARI, AHMAD+

  DOI：——

  日期：——
• US4539412A
  申请人：——

  公开号：US4539412A

  公开（公告）日：1985-09-03
• Analogs of hycanthone and lucanthone as antitumor agents
  作者：Sydney Archer、Abdel Hadi Zayed、Rabindra Rej、Thomas A. Rugino

  DOI：10.1021/jm00363a007

  日期：1983.9

  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.
• 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。