Phenyl-(3-m-tolyl-thioureido)-acetic acid

• 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: Phenyl-(3-m-tolyl-thioureido)-acetic acid
• 英文别名: 2-[(3-Methylphenyl)carbamothioylamino]-2-phenylacetic acid
• 化学式: C₁₆H₁₆N₂O₂S
• 分子量: 300.381
• InChiKey: SYSPYNBYFWTQSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Phenyl-(3-m-tolyl-thioureido)-acetic acid 在 盐酸 作用下， 以 水 为溶剂， 生成 5-Phenyl-2-thioxo-3-m-tolyl-imidazolidin-4-one
  参考文献：
  名称：

  Synthesis, molecular modelling and enzymatic evaluation of (±)3,5-diphenyl-2-thioxoimidazolidin-4-ones as new potential cyclooxygenase inhibitors

  摘要：

  A series of substituted (+/-)3,5-diphenyl-2-thioxoimidazolin-4-ones was synthesized in order to design new type-2 cyclooxygenase (COX-2) inhibitors. This study has led to Molecules which completely inhibit human recombinant COX-2 at 50 mu M. Molecular modelling highlighted drug interactions with the active site of both cyclooxygenases and suggested modifications to enhance the selectivity of the compounds. In human blood, COX-2 expression was then induced by LPS, and the inhibitory potency of these drugs was disappointing. This weak activity was attributed to a poor aqueous stability of these imidazolidinones Substituted by two aryl in position 3 and 5 (15 min < t(1/2) < 130 min). The improvement of the stability of this heterocycle Could generate a novel template to treat COX-associated diseases Such as arthritis, rheumatoid polyarthritis and cancer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.005
• 作为产物：
  描述：

  2-氨基-2-苯基乙酸 、 间甲苯异硫氰酸酯 在 吡啶 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.5h， 生成 Phenyl-(3-m-tolyl-thioureido)-acetic acid
  参考文献：
  名称：

  Synthesis, molecular modelling and enzymatic evaluation of (±)3,5-diphenyl-2-thioxoimidazolidin-4-ones as new potential cyclooxygenase inhibitors

  摘要：

  A series of substituted (+/-)3,5-diphenyl-2-thioxoimidazolin-4-ones was synthesized in order to design new type-2 cyclooxygenase (COX-2) inhibitors. This study has led to Molecules which completely inhibit human recombinant COX-2 at 50 mu M. Molecular modelling highlighted drug interactions with the active site of both cyclooxygenases and suggested modifications to enhance the selectivity of the compounds. In human blood, COX-2 expression was then induced by LPS, and the inhibitory potency of these drugs was disappointing. This weak activity was attributed to a poor aqueous stability of these imidazolidinones Substituted by two aryl in position 3 and 5 (15 min < t(1/2) < 130 min). The improvement of the stability of this heterocycle Could generate a novel template to treat COX-associated diseases Such as arthritis, rheumatoid polyarthritis and cancer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.005