2-(4-chlorophenyl)-1,3-di(morpholin-4-yl)propenethione | 156483-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-chlorophenyl)-1,3-di(morpholin-4-yl)propenethione
• 英文别名: 2-(4-Chlorophenyl)-1,3-dimorpholin-4-ylprop-2-ene-1-thione；2-(4-chlorophenyl)-1,3-dimorpholin-4-ylprop-2-ene-1-thione
• CAS: 156483-09-9
• 化学式: C₁₇H₂₁ClN₂O₂S
• 分子量: 352.885
• InChiKey: RAOVEIJJGJLXRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-1,3-di(morpholin-4-yl)propenethione 在 氢氧化钾 、 碘 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 4-(4-chlorophenyl)-3-morpholinopyrrole
  参考文献：
  名称：

  Synthesis, Anticonvulsant Activity, and Structure−Activity Relationships of Sodium Channel Blocking 3-Aminopyrroles

  摘要：

  Starting from the corresponding acetophenone and glycine derivatives, a series of new 3-aminopyrroles was synthesized in few steps. Using this procedure with hydrazine and hydroxylamine instead of the glycinates provides access to S-aminopyrazoles and 5-amino-1,2-oxazoles. The various derivatives were tested for anticonvulsant activity in a variety of test models. Several compounds exhibit considerable activity with a remarkable lack of neurotoxicity. 4-(4-Bromophenyl)-3-morpholinopyrrole-2-carboxylic acid methyl ester, 3, proved to be the most active compound. It was protective in the maximal electroshock seizure (MES) test in rats with an oral ED50 of 2.5 mg/kg with no neurotoxicity noted at doses up to 500 mg/kg. Compound 3 blocks sodium channels in a frequency-dependent manner. The essential structural features which could be responsible for an interaction with an active site of the voltage-dependent sodium channel are established within a suggested pharmacophore model.

  DOI：

  10.1021/jm970327j
• 作为产物：
  描述：

  trimorpholylmethane 、 2-(4-chlorophenyl)-1-(morpholin-4-yl)-ethanethione 以 neat (no solvent) 、 melt 为溶剂， 反应 0.5h， 以93.6%的产率得到2-(4-chlorophenyl)-1,3-di(morpholin-4-yl)propenethione
  参考文献：
  名称：

  Efficient Synthesis of 3-Aminothioacrylamides by Iminoformylation of Thioacetamides

  摘要：

  将取代的硫代乙酰胺 1 与三吗啉甲烷或原甲酸三乙酯和仲胺的混合物一起加热，可以得到高产率的合成用途广泛的 3-氨基硫代丙烯酰胺 4。

  DOI：

  10.1055/s-1994-25545

文献信息

• Design, synthesis and evaluation of novel 2-thiophen-5-yl-3H-quinazolin-4-one analogues as inhibitors of transcription factors NF-кB and AP-1 mediated transcriptional activation: Their possible utilization as anti-inflammatory and anti-cancer agents
  作者：Rajan S. Giri、Hardik M. Thaker、Tony Giordano、Jill Williams、Donna Rogers、Kamala K. Vasu、Vasudevan Sudarsanam

  DOI：10.1016/j.bmc.2010.01.007

  日期：2010.4

  inhibitors of NF-κB and AP-1 mediated transcriptional activation utilizing the concept of chemical lead based medicinal chemistry and bioisosterism a series of 2-(2,3-disubstituted-thiophen-5-yl)-3H-quinazolin-4-one analogs was designed. A facile and simple route for the synthesis of the designed molecules was developed. Synthesized molecules were evaluated for their activity as inhibitors towards NF-кB

  为了利用基于化学铅的药物化学和生物立体异构的概念来发现新的NF-κB和AP-1介导的转录激活抑制剂，一系列2-（2,3-二取代-噻吩-5-基）-3 H设计了喹喹啉-4-酮类似物。开发了一种简单易行的合成设计分子的途径。在基于细胞系报告的分析中评估了合成分子作为针对NF-кB和AP-1介导的转录激活的抑制剂的活性。该系列为我们提供了许多抑制NF-кB和/或AP-1介导的转录激活活性的化合物。这些化合物在炎症和癌症的体内模型中还显示出抗炎和抗癌活性。发现4-吡啶基是噻吩环第三位置上最重要的抑制NF- κ的药效基团B和AP-1介导的转录激活。这些化合物在体内和体外模型中显示的活性之间的关系已通过使用FVB转基因小鼠模型建立。这些结果表明，所设计的分子框架适合作为潜在支架，用于设计对NF-κB和AP-1介导的转录激活具有抑制活性的分子，该分子也可能表现出抗炎和抗癌活性。这一系列分子值得进一步研究，
• 3-Amino- and 5-Aminopyrazoles with Anticonvulsant Activity
  作者：Hans-Joachim Lankau、Manfred Menzer、Angelika Rostock、Thomas Arnold、Chris Rundfeldt、Klaus Unverferth

  DOI：10.1002/(sici)1521-4184(19996)332:6<219::aid-ardp219>3.0.co;2-t

  日期：1999.6

  New 3‐amino‐ and 5‐aminopyrazoles were synthesised. 3‐Aminopyrazoles exert a strong anticonvulsant effect. 4‐Chlorophenyl‐3‐( morpholin‐4‐yl)‐1H‐pyrazole 2 distinctively blocks sodium channels and is strongly effective in the Maximal Electroshock Seizure (MES) test.

  合成了新的 3-氨基和 5-氨基吡唑。3-氨基吡唑类药物具有很强的抗惊厥作用。4 - Chlorophenyl - 3- (morpholin - 4-yl) -1H - pyrazole 2 独特地阻断钠通道并且在最大电休克癫痫 (MES) 测试中非常有效。
• THIAZOLE AND THIOPHENE ANALOGUES, AND THEIR USE IN TREATING AUTOIMMUNE DISEASES AND CANCERS
  申请人：Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College

  公开号：EP2007393A2

  公开（公告）日：2008-12-31
• Thiazole and Thiophene Analogues, and Their Use in Treating Autoimmune Diseases and Cancers
  申请人：Giordano Anthony

  公开号：US20090306073A1

  公开（公告）日：2009-12-10

  Thiazole and thiophene compounds are disclosed having utility in treating inflammatory conditions, immunoinflammatory conditions, autoimmune diseases, and cancers. Methods for the synthesis of these compounds are also disclosed.
• US8217037B2
  申请人：——

  公开号：US8217037B2

  公开（公告）日：2012-07-10