4-(5-methyl-1,2,4-oxadiazol-3-yl)-N-(3,3,3-trifluoropropyl)benzamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-methyl-1,2,4-oxadiazol-3-yl)-N-(3,3,3-trifluoropropyl)benzamide
• 化学式: C₁₃H₁₂F₃N₃O₂
• 分子量: 299.252
• InChiKey: IZNKJTRPPITJIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对氰基苯甲酸 在 盐酸羟胺 、 溶剂黄146 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 生成 4-(5-methyl-1,2,4-oxadiazol-3-yl)-N-(3,3,3-trifluoropropyl)benzamide
  参考文献：
  名称：

  COMPOUNDS FOR USE IN THE TREATMENT OF MYCOBACTERIAL INFECTIONS

  摘要：

  本发明涉及通式（I）的化合物： 其中Y和Z从CH和N中选择；T从CO或SO2中选择；n为1到3；R1代表选择的一种基团，例如从C1-C3烷基链中未取代或取代的氟，未取代或取代的环状，氰基，偶氮基，烷氧基和苯基；R从偶氮基，氰基，炔烃基和2-苯并噻唑基以及一个可选择取代的具有五个顶点的芳香杂环中选择；以及其在治疗细菌和分枝杆菌感染，如肺结核、麻风和非典型分枝杆菌感染中的用途。本发明还涉及包含上述化合物中至少一种和可选通过EthA途径激活的抗生素作为活性成分的药物组合物。

  公开号：

  US20150225388A1

文献信息

• COMPOUNDS FOR USE IN THE TREATMENT OF MYCOBACTERIAL INFECTIONS
  申请人：UNIVERSITE DE DROIT ET DE LA SANTE DE LILLE 2

  公开号：US20150225388A1

  公开（公告）日：2015-08-13

  The present invention concerns compounds of general formula (I): in which Y and Z are chosen from CH and N; T is chosen from CO or SO 2 ; n is 1 to 3; R1 represents a group chosen, for example, from C1-C3 alkyl chains unsubstituted or substituted by fluorine, the unsubstituted or substituted cyclic, cyano, azido, alkoxy and phenyl groups; and R is chosen from the azido, cyano, alkinyl and 2-benzothiazolyl groups and an optionally substituted aromatic heterocycle with five vertices; and the use thereof in the treatment of bacterial and mycobacterial infections such as, for example, tuberculosis, leprosy and atypical mycobacterial infections. The present invention also concerns pharmaceutical compositions comprising, as the active ingredient, at least one of the abovementioned compounds and optionally an antibiotic activatable via the EthA pathway

  本发明涉及通式（I）的化合物： 其中Y和Z从CH和N中选择；T从CO或SO2中选择；n为1到3；R1代表选择的一种基团，例如从C1-C3烷基链中未取代或取代的氟，未取代或取代的环状，氰基，偶氮基，烷氧基和苯基；R从偶氮基，氰基，炔烃基和2-苯并噻唑基以及一个可选择取代的具有五个顶点的芳香杂环中选择；以及其在治疗细菌和分枝杆菌感染，如肺结核、麻风和非典型分枝杆菌感染中的用途。本发明还涉及包含上述化合物中至少一种和可选通过EthA途径激活的抗生素作为活性成分的药物组合物。
• COMPOSES UTILISABLES DANS LE TRAITEMENT DES INFECTIONS MYCOBACTERIENNES
  申请人：Université de Droit et de la Santé de Lille 2

  公开号：EP2900638A1

  公开（公告）日：2015-08-05
• US9920042B2
  申请人：——

  公开号：US9920042B2

  公开（公告）日：2018-03-20
• Fragment-Based Optimized EthR Inhibitors with <i>in Vivo</i> Ethionamide Boosting Activity
  作者：Baptiste Villemagne、Arnaud Machelart、Ngoc Chau Tran、Marion Flipo、Martin Moune、Florence Leroux、Catherine Piveteau、Alexandre Wohlkönig、René Wintjens、Xue Li、Ruxandra Gref、Priscille Brodin、Benoit Deprez、Alain R Baulard、Nicolas Willand

  DOI：10.1021/acsinfecdis.9b00277

  日期：2020.3.13

  Killing more than one million people each year, tuberculosis remains the leading cause of death from a single infectious agent. The growing threat of multidrug-resistant strains of Mycobacterium tuberculosis stresses the need for alternative therapies. EthR, a mycobacterial transcriptional regulator, is involved in the control of the bioactivation of the second-line drug ethionamide. We have previously reported the discovery of in vitro nanomolar boosters of ethionamide through fragment-based approaches. In this study, we have further explored the structure-activity and structure-property relationships in this chemical family. By combining structure-based drug design and in vitro evaluation of the compounds, we identified a new oxadiazole compound as the first fragment-based ethionamide booster which proved to be active in vivo, in an acute model of tuberculosis infection.