N-(3,4,5-trimethoxyphenyl)-3,5-difluorothiobenzamide | 1036377-85-1

• 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: N-(3,4,5-trimethoxyphenyl)-3,5-difluorothiobenzamide
• 英文别名: 3,5-difluoro-N-(3,4,5-trimethoxyphenyl)benzenecarbothioamide
• CAS: 1036377-85-1
• 化学式: C₁₆H₁₅F₂NO₃S
• 分子量: 339.363
• InChiKey: ZMDHOFZGARFHCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  71.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  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

文献信息

• [DE] BENZOTHIOAMIDE UND DEREN VERWENDUNG<br/>[EN] BENZOTHIOAMIDES, AND USE THEREOF<br/>[FR] BENZOTHIOAMIDES ET LEUR UTILISATION
  申请人：UNIV WIEN

  公开号：WO2008077170A2

  公开（公告）日：2008-07-03

  [EN] The invention relates to the use of a compound of general formula (I), wherein Y is selected from among the group comprising thienyl, pyridyl, and formula (a), wherein each radical R represents hydrogen or a substituent selected from among the group comprising F, Cl, Br, I, OH, OCH₃, NO₂, CF₃, CH₃, OCF₃, N(CH₃)₂, and SCH₃, provided that at least one radical R does not represent hydrogen, X represents an unsubstituted or substituted aryl group, one or more ring atoms being substituted with a radical selected from among the group comprising F, Cl, Br, I, OH, OCH₃, NO₂, CF₃, CH₃, OCF₃, N(CH₃)₂, and SCH₃, and n, m = 0 or 1, as well as the salts thereof for producing a medicament for relaxing smooth muscles. Also disclosed are particularly suitable groups of compounds of formula (I).
  [FR] L'invention concerne l'utilisation d'un composé de formule (I), dans laquelle Y est choisi dans le groupe comprenant le thiényle, le pyridyle et un groupe de formule (a), chaque reste R désignant l'hydrogène ou un substituant choisi dans le groupe comprenant F, Cl, Br, I, OH, OCH₃, NO₂, CF₃, CH₃, OCF₃, N(CH₃)₂ et SCH₃, sous réserve qu'au moins un reste R n'est pas un hydrogène, X désigne un groupe aryle non substitué ou substitué, un ou plusieurs atomes du noyau étant substitués par un reste choisi dans le groupe comprenant F, Cl, Br, I, OH, OCH₃, NO₂, CF₃, CH₃, OCF₃, N(CH₃)₂ et SCH₃, et n, m = 0 ou 1, ainsi que les sels de ce composé pour la production d'un médicament destiné à la relaxation des muscles lisses. L'invention concerne également des groupes de composés de formule (I) particulièrement appropriés.
  [DE] Die Erfindung betrifft die Verwendung einer Verbindung der allgemeinen Formel (I), wobei Y ausgewählt ist aus der Gruppe bestehend aus Thienyl, Pyridyl und Formel (a), wobei jeder Rest R Wasserstoff oder ein Substituent, ausgewählt aus der Gruppe bestehend aus F, Cl, Br, I, OH, OCH₃, NO₂, CF₃, CH₃, OCF₃, N(CH₃)₂ und SCH₃, ist, mit der Maßgabe, dass mindestens ein Rest R nicht Wasserstoff ist, X eine unsubstituierte oder substituierte Arylgruppe ist, wobei ein oder mehrere Ringatome mit einem Rest, ausgewählt aus der Gruppe bestehend aus F, Cl, Br, I, OH, OCH₃, NO₂, CF₃, CH₃, OCF₃, N(CH₃)₂ und SCH₃, substituiert sind, und n, m = 0 oder 1, und deren Salze zur Herstellung eines Arzneimittels zur Relaxierung glatter Muskulatur, sowie besonders geeignete Verbindungsgruppen der Formel (I).
• 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.