1-[[2-(diethylamino)ethyl]amino]-7-methoxy-9-oxothioxanthen-4-carboxaldehyde | 86456-08-8

• 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-(diethylamino)ethyl]amino]-7-methoxy-9-oxothioxanthen-4-carboxaldehyde
• 英文别名: 1-{[2-(diethylamino)ethyl]amino}-7-methoxy-9-oxo-9H-thioxanthene-4-carboxaldehyde；1-[2-(diethylamino)ethylamino]-7-methoxy-9-oxothioxanthene-4-carbaldehyde
• CAS: 86456-08-8
• 化学式: C₂₁H₂₄N₂O₃S
• 分子量: 384.499
• InChiKey: YJWSPUGSBXWTSA-UHFFFAOYSA-N

物化性质

• 沸点：
  591.8±50.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[[2-(diethylamino)ethyl]amino]-7-methoxy-9-oxothioxanthen-4-carboxaldehyde 以69的产率得到N-[1-(2-diethylamino-ethylamino)-7-methoxy-9-oxo-9H-thioxanthen-4-ylmethyl]formamide
  参考文献：
  名称：

  Thioxanthenone antitumor agents

  摘要：

  本文介绍了1-[[(二烷基氨基)烷基]氨基]-4-取代硫代黄酮-9-酮作为抗肿瘤剂的应用。同时还公开了含有硫代黄酮酮类化合物的组合物以及使用该类化合物治疗哺乳动物肿瘤和癌症的方法。

  公开号：

  US05346917A1
• 作为产物：
  描述：

  间氯溴苯 在 manganese(IV) oxide 、 PPA 、 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 46.0h， 生成 1-[[2-(diethylamino)ethyl]amino]-7-methoxy-9-oxothioxanthen-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

• Lyophilized thioxanthenone antitumor agents
  申请人：Sanofi Winthrop, Inc.

  公开号：US05665760A1

  公开（公告）日：1997-09-09

  Disclosed are reconstituted lyophilized formulations for the treatment of mammalian tumors comprising a thioxanthenone antitumor agent in combination with mannitol or sucrose as a stabilizer in a lactate buffer.

  公开了用于治疗哺乳动物肿瘤的重组冻干制剂，该制剂包括一种噻吨酮类抗肿瘤剂，并与乳糖酸缓冲液中的甘露醇或蔗糖作为稳定剂结合使用。
• [EN] LYOPHILIZED THIOXANTHENONE ANTIMUMOR AGENTS<br/>[FR] THIOXANTHENONE LYOPHILISEE COMME AGENTS ANTITUMORAUX
  申请人：SANOFI

  公开号：WO1997010809A1

  公开（公告）日：1997-03-27

  (EN) Disclosed are reconstituted lyophilized formulations for the treatment of mammalian tumors comprising a thioxanthenone antitumor agent in combination with mannitol or sucrose as a stabilizer in a lactate buffer.(FR) La présente invention concerne des formulations lyophilisées reconstituées destinées au traitement de tumeurs de mammifères. Ces formulations comprennent un agent antitumoral, à savoir la thioxanthénone, combinée à un stabilisant, en l'occurrence le mannitol ou le saccharose, dans un tampon de lactate.

  揭示了一种重组冻干配方，用于治疗哺乳动物肿瘤，包括一种硫代三环酮抗肿瘤剂与甘露醇或蔗糖作为稳定剂，在乳酸缓冲液中组合使用。
• Synthesis and Antitumor Activity of 4-Aminomethylthioxanthenone and 5-Aminomethylbenzothiopyranoindazole Derivatives
  作者：Robert B. Perni、Mark P. Wentland、Jianhua I. Huang、Ronald G. Powles、Suzanne Aldous、Kristina M. Klingbeil、A. Danielle Peverly、Ronald G. Robinson、Thomas H. Corbett、Julie L. Jones、Kenneth C. Mattes、James B. Rake、Susan A. Coughlin

  DOI：10.1021/jm9708083

  日期：1998.9.1

  Two new series of antitumor agents, 4-aminomethylthioxanthenones (6-50) and 5-aminomethylbenzothiopyranoindazoles (51-61), are described and compared. Nearly all members of both series display excellent in vivo activity versus murine pancreatic adenocarcinoma 03 (Panc03) although there is little to distinguish the two series from each other. In both series there is no discernible relationship between structure and in vivo efficacy. Selected analogues were evaluated in vitro; all were observed to have moderate to strong DNA binding via intercalation. However, varying degrees of in vitro P388 cytotoxicity and topoisomerase II inhibition were seen. In general, those molecules which exhibited strong topoisomerase II inhibition were significantly more cytotoxic than those which did not. In both series, those derivatives (48-50, 60, and 61) having a phenolic hydroxy substitution exhibited the most potent P388 cytotoxicity and topoisomerase II inhibition.
• 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：——