N-[[1-[[2-(diethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]formamide | 146537-03-3

• 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: N-[[1-[[2-(diethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]formamide
• 英文别名: N-[1-(2-diethylamino-ethylamino)-9-oxo-9H-thioxanthen-4-ylmethyl]formamide；N-[[1-[2-(diethylamino)ethylamino]-9-oxothioxanthen-4-yl]methyl]formamide
• CAS: 146537-03-3
• 化学式: C₂₁H₂₅N₃O₂S
• 分子量: 383.514
• InChiKey: SFDBHPJUOZSMJY-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156 °C
• 沸点：
  645.8±55.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  86.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[[1-[[2-(diethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]formamide 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 N-[[1-[[2-(diethylamino)ethyl]amino]-9-oxo-9H-thiaxanthen-4-yl]methyl]methanesulfonamide
  参考文献：
  名称：

  Synthesis and Antitumor Activity of 4-Aminomethylthioxanthenone and 5-Aminomethylbenzothiopyranoindazole Derivatives

  摘要：

  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.

  DOI：

  10.1021/jm9708083
• 作为产物：
  描述：

  1-[[2-(diethylamino)-ethyl]amino]-9-oxo-thioxanthen-4-carboxaldehyde 生成 N-[[1-[[2-(diethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]formamide
  参考文献：
  名称：

  J. Med. Chem. 1998, 41, 3645-3654

  摘要：

  DOI：

文献信息

• Thioxanthenone antitumor agents
  申请人：Sterling Winthrop Inc.

  公开号：US05346917A1

  公开（公告）日：1994-09-13

  1-[[(Dialkylamino)alkyl]amino]-4-substituted-thioxanthen-9-ones are disclosed as antitumor agents. Compositions containing the thioxanthenones and methods of treating tumors and cancer in mammals with the thioxanthenones are also disclosed.

  1-[[(二烷基氨基)烷基]氨基]-4-取代-噻吨-9-酮被披露为抗肿瘤剂。还披露了含有噻吨酮的制剂以及使用噻吨酮治疗哺乳动物肿瘤和癌症的方法。
• 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。
• One Step Synthesis of <i>N</i>-[1-(2-Diethylamino-ethylamino)-7-(<i>H</i> or methoxy)-9-oxo-9<i>H</i>-thioxanthen-4-ylmethyl]-formamides and, Acetamide from Their Corresponding Alcohols, Hycanthone, and 7-Methoxy-hycanthone
  作者：Hua-Zhong He、Chul-Hoon Kwon

  DOI：10.1081/scc-120021833

  日期：2003.1.8

  Abstract N-[1-(2-Diethylamino-ethylamino)-7-(H or methoxy)-9-oxo-9H-thioxanthen-4-ylmethyl]-formamides and acetamide were synthesized from their corresponding alcohols, hycanthone and 7-methoxy-hycanthone, in one step procedure and 45% yield.

  摘要 N-[1-(2-二乙氨基-乙氨基)-7-(H 或甲氧基)-9-氧代-9H-噻吨-4-基甲基]-甲酰胺和乙酰胺由其相应的醇、乙氧基和7-甲氧基合成。 -hycanthone，一步法，产率45%。
• [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。
• LYOPHILIZED THIOXANTHENONE ANTIMUMOR AGENTS
  申请人：SANOFI

  公开号：EP0917458A1

  公开（公告）日：1999-05-26