3,5-difluoro-N-(3,4,5-trimethoxyphenyl)benzamide | 941099-41-8

• 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: 3,5-difluoro-N-(3,4,5-trimethoxyphenyl)benzamide
• CAS: 941099-41-8
• 化学式: C₁₆H₁₅F₂NO₄
• 分子量: 323.296
• InChiKey: PDERYYPKKOXQDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-difluoro-N-(3,4,5-trimethoxyphenyl)benzamide 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到N-(3,4,5-trimethoxyphenyl)-3,5-difluorothiobenzamide
  参考文献：
  名称：

  Synthesis, spasmolytic activity and structure–activity relationship study of a series of polypharmacological thiobenzanilides

  摘要：

  Recently we presented a series of benzanilide derivatives with a selective spasmolytic effect on terminal ileum preparations of the guinea pig. In this report we demonstrate a further development of these compounds. The exchange of the amide oxygen against a sulfur atom resulted in an up to 325 fold increase of the antispasmodic activity of the thiobenzanilide (IC50 of 0.1 mu M) compared to its benzanilide derivative. Considering their mode of action the compounds interacted with several molecular targets, suggesting that we identified a chemical identity able to modulate multiple targets simultaneously. Furthermore, based on this data set, we present a structure-activity relationship study supporting the important role of the sulfur atom. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2010.10.005
• 作为产物：
  描述：

  3,5-二氟苯甲酰氯 、 3,4,5-三甲氧基苯胺 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以88%的产率得到3,5-difluoro-N-(3,4,5-trimethoxyphenyl)benzamide
  参考文献：
  名称：

  Benzanilides with spasmolytic activity: Chemistry, pharmacology, and SAR

  摘要：

  The following study describes the synthesis of new benzanilide derivatives and their pharmacological investigation on smooth muscle preparations of guinea pigs. All compounds were synthesized in good yields and showed a spasmolytic activity without significant effect on vascular smooth muscles and heart muscle preparations. Moreover, further pharmacological investigations as well as in silico studies were performed to elucidate the mechanism of action. Compound 3 showed the most potent spasmolytic activity with an IC(50) of 3.25 mu M. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.057

文献信息

• Benzanilides with spasmolytic activity: Chemistry, pharmacology, and SAR
  作者：Gerda Brunhofer、Norbert Handler、Klaus Leisser、Christian R. Studenik、Thomas Erker

  DOI：10.1016/j.bmc.2008.04.057

  日期：2008.6

  The following study describes the synthesis of new benzanilide derivatives and their pharmacological investigation on smooth muscle preparations of guinea pigs. All compounds were synthesized in good yields and showed a spasmolytic activity without significant effect on vascular smooth muscles and heart muscle preparations. Moreover, further pharmacological investigations as well as in silico studies were performed to elucidate the mechanism of action. Compound 3 showed the most potent spasmolytic activity with an IC(50) of 3.25 mu M. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis, spasmolytic activity and structure–activity relationship study of a series of polypharmacological thiobenzanilides
  作者：Gerda Brunhofer、Christian Studenik、Gerhard F. Ecker、Thomas Erker

  DOI：10.1016/j.ejps.2010.10.005

  日期：2011.1

  Recently we presented a series of benzanilide derivatives with a selective spasmolytic effect on terminal ileum preparations of the guinea pig. In this report we demonstrate a further development of these compounds. The exchange of the amide oxygen against a sulfur atom resulted in an up to 325 fold increase of the antispasmodic activity of the thiobenzanilide (IC50 of 0.1 mu M) compared to its benzanilide derivative. Considering their mode of action the compounds interacted with several molecular targets, suggesting that we identified a chemical identity able to modulate multiple targets simultaneously. Furthermore, based on this data set, we present a structure-activity relationship study supporting the important role of the sulfur atom. (C) 2010 Elsevier B.V. All rights reserved.