3-[(4-methylphenyl)methyl]-6-methylsulfanyl-1H-1,3,5-triazine-2,4-dione | 1616092-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 3-[(4-methylphenyl)methyl]-6-methylsulfanyl-1H-1,3,5-triazine-2,4-dione
• CAS: 1616092-03-5
• 化学式: C₁₂H₁₃N₃O₂S
• 分子量: 263.32
• InChiKey: YGERWXRVOIWJTG-UHFFFAOYSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(4-methylphenyl)methyl]-6-methylsulfanyl-1H-1,3,5-triazine-2,4-dione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 60.0h， 生成 6-((2-aminoethyl)amino)-1-(3,4-dichlorobenzyl)-3-(4-methylbenzyl)-1,3,5-triazine-2,4(1H,3H)-dione
  参考文献：
  名称：

  A new convenient synthetic method and preliminary pharmacological characterization of triazinediones as prokineticin receptor antagonists

  摘要：

  A new efficient synthetic method to obtain prokineticin receptor antagonists based on the triazinedione scaffold is described. In this procedure the overall yield improves from 13% to about 54%, essentially for two factors: 1) N-(chlorocarbonyl) isocyanate is no more used, it represents the yield limiting step with an average yield not exceeding 30%. 2) The Mitsunobu reaction is not involved in the new synthetic scheme avoiding the use of time and solvent consuming column chromatography. All synthesized triazinediones were preliminary pharmacologically screened in vivo for their ability to reduce the Bv8-induced thermal hyperalgesia. In this assay all compounds displayed EC50 values in the picomolar-subpicomolar range, some triazinediones containing a 4-halogen substituted benzyl group in position 5 showed the best activity. The analogues containing a 4-fluorine atom (PC-7) and a 4-bromobenzyl group (PC-25) resulted 10 times more potent than the reference PC-1 that bears a 4-ethylbenzyl group. While the 4-trifluoromethylbenzyl substituted analog (PC-27) was 100 times more potent as compared to PC1. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.030
• 作为产物：
  描述：

  N-(4-甲基苄基)脲 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 7.5h， 生成 3-[(4-methylphenyl)methyl]-6-methylsulfanyl-1H-1,3,5-triazine-2,4-dione
  参考文献：
  名称：

  A new convenient synthetic method and preliminary pharmacological characterization of triazinediones as prokineticin receptor antagonists

  摘要：

  A new efficient synthetic method to obtain prokineticin receptor antagonists based on the triazinedione scaffold is described. In this procedure the overall yield improves from 13% to about 54%, essentially for two factors: 1) N-(chlorocarbonyl) isocyanate is no more used, it represents the yield limiting step with an average yield not exceeding 30%. 2) The Mitsunobu reaction is not involved in the new synthetic scheme avoiding the use of time and solvent consuming column chromatography. All synthesized triazinediones were preliminary pharmacologically screened in vivo for their ability to reduce the Bv8-induced thermal hyperalgesia. In this assay all compounds displayed EC50 values in the picomolar-subpicomolar range, some triazinediones containing a 4-halogen substituted benzyl group in position 5 showed the best activity. The analogues containing a 4-fluorine atom (PC-7) and a 4-bromobenzyl group (PC-25) resulted 10 times more potent than the reference PC-1 that bears a 4-ethylbenzyl group. While the 4-trifluoromethylbenzyl substituted analog (PC-27) was 100 times more potent as compared to PC1. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.030

文献信息

• PROKINETICIN 1 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF PAIN
  申请人：Flores Christopher M.

  公开号：US20110319400A1

  公开（公告）日：2011-12-29

  Disclosed are compounds, compositions and methods for treating pain, including inflammatory, visceral, and acute pain. Such compounds are represented by Formula (I) as follows: wherein A 1 , L 1 , D, and Q are defined herein.

  披露了用于治疗疼痛的化合物、组合物和方法，包括炎症性、内脏性和急性疼痛。这些化合物由以下式（I）表示： 其中A1、L1、D和Q在此处定义。
• PROKINETICIN 1 RECEPTOR ANTAGONISTS
  申请人：Coats Steven J.

  公开号：US20120028997A1

  公开（公告）日：2012-02-02

  The present invention relates to certain novel compounds of Formula (I): and methods for preparing these compounds, compositions, intermediates and derivatives thereof and for the treatment of prokineticin 1 or prokinetin 1 receptor mediated disorders.
• US8372973B2
  申请人：——

  公开号：US8372973B2

  公开（公告）日：2013-02-12
• A new convenient synthetic method and preliminary pharmacological characterization of triazinediones as prokineticin receptor antagonists
  作者：Cenzo Congiu、Valentina Onnis、Alessandro Deplano、Severo Salvadori、Veronica Marconi、Daniela Maftei、Lucia Negri、Roberta Lattanzi、Gianfranco Balboni

  DOI：10.1016/j.ejmech.2014.05.030

  日期：2014.6

  A new efficient synthetic method to obtain prokineticin receptor antagonists based on the triazinedione scaffold is described. In this procedure the overall yield improves from 13% to about 54%, essentially for two factors: 1) N-(chlorocarbonyl) isocyanate is no more used, it represents the yield limiting step with an average yield not exceeding 30%. 2) The Mitsunobu reaction is not involved in the new synthetic scheme avoiding the use of time and solvent consuming column chromatography. All synthesized triazinediones were preliminary pharmacologically screened in vivo for their ability to reduce the Bv8-induced thermal hyperalgesia. In this assay all compounds displayed EC50 values in the picomolar-subpicomolar range, some triazinediones containing a 4-halogen substituted benzyl group in position 5 showed the best activity. The analogues containing a 4-fluorine atom (PC-7) and a 4-bromobenzyl group (PC-25) resulted 10 times more potent than the reference PC-1 that bears a 4-ethylbenzyl group. While the 4-trifluoromethylbenzyl substituted analog (PC-27) was 100 times more potent as compared to PC1. (C) 2014 Elsevier Masson SAS. All rights reserved.