N-(prop-2-yn-1-yl)-4-(trifluoromethoxy)benzamide

• 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-(prop-2-yn-1-yl)-4-(trifluoromethoxy)benzamide
• 英文别名: N-prop-2-ynyl-4-(trifluoromethoxy)benzamide
• 化学式: C₁₁H₈F₃NO₂
• mdl: MFCD17646012
• 分子量: 243.185
• InChiKey: LAWLETDOJIIYNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(prop-2-yn-1-yl)-4-(trifluoromethoxy)benzamide 在 lithium hydroxide monohydrate 、 potassium tert-butylate 、 水 、 三溴化硼 、 zinc trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 (R)-3-methyl-6-(2-((5-methyl-2-(4-(trifluoromethoxy)phenyl)-1H-imidazol-1-yl)methyl)phenoxy)hexanoic acid
  参考文献：
  名称：

  Selective PPARδ Modulators Improve Mitochondrial Function: Potential Treatment for Duchenne Muscular Dystrophy (DMD)

  摘要：

  The X-ray structure of the previously reported PPAR delta modulator 1 bound to the ligand binding domain (LBD) revealed that the amide moiety in 1 exists in the thermodynamically disfavored cis-amide orientation. Isosteric replacement of the cis-amide with five-membered heterocycles led to the identification of imidazole 17 (MA-0204), a potent, selective PPAR delta modulator with good pharmacokinetic properties. MA-0204 was tested in vivo in mice and in vitro in patient derived muscle myoblasts (from Duchenne Muscular Dystrophy (DMD) patients); 17 altered the expression of PPAR delta target genes and improved fatty acid oxidation, which supports the therapeutic hypothesis for the study of MA-0204 in DMD patients.

  DOI：

  10.1021/acsmedchemlett.8b00287
• 作为产物：
  描述：

  炔丙胺 、 4-三氟甲氧基苯甲酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以95.4%的产率得到N-(prop-2-yn-1-yl)-4-(trifluoromethoxy)benzamide
  参考文献：
  名称：

  [EN] PPAR AGONISTS, COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
  [FR] AGONISTES DE PPAR, COMPOSÉS, COMPOSITIONS PHARMACEUTIQUES ET MÉTHODES D'UTILISATION DE CEUX-CI

  摘要：

  公开号：

  WO2017062468A8

文献信息

• TBAI-Mediated Cyclization and Methylsulfonylation of Propargylic Amides with Dimethyl Sulfite
  作者：Jia-Qing Zhuang、Ying-Qiong Guo、Chen-Liang Deng、Xing-Guo Zhang、Hai-Yong Tu

  DOI：10.1021/acs.joc.3c00785

  日期：2023.8.4

  A tetramethylammonium iodide (TBAI)-mediated cyclization and methylsulfonylation of propargylic amides enabled by dimethyl sulfite as a SO2 surrogate and methyl source have been developed. The transition metal-free and oxidant-free reaction provides a practical and efficient approach for the selective synthesis of methylsulfonyl oxazoles in moderate to excellent yields with good functional group compatibility

  已经开发出四甲基碘化铵 (TBAI) 介导的炔丙酰胺环化和甲基磺酰化，通过亚硫酸二甲酯作为 SO 2替代物和甲基源实现。无过渡金属和无氧化剂的反应为选择性合成甲磺酰恶唑提供了一种实用且有效的方法，具有中等至优异的产率和良好的官能团相容性。
• PPAR agonists, compounds, pharmaceutical compositions, and methods of use thereof
  申请人：Mitobridge, Inc.

  公开号：US10399958B2

  公开（公告）日：2019-09-03

  Provided herein are compounds I, II or III and compositions useful in increasing PPAR8 activity. The compounds and compositions provided herein are useful for the treatment of PPAR8 related diseases (e.g., muscular diseases, vascular disease, demyelinating disease, and metabolic diseases).

  本文提供了可提高 PPAR8 活性的化合物 I、II 或 III 及组合物。本文提供的化合物和组合物可用于治疗 PPAR8 相关疾病（如肌肉疾病、血管疾病、脱髓鞘疾病和代谢性疾病）。
• [EN] PPAR AGONISTS, COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF<br/>[FR] AGONISTES DE PPAR, COMPOSÉS, COMPOSITIONS PHARMACEUTIQUES ET MÉTHODES D'UTILISATION DE CEUX-CI
  申请人：MITOBRIDGE INC

  公开号：WO2017062468A8

  公开（公告）日：2017-05-11
• Selective PPARδ Modulators Improve Mitochondrial Function: Potential Treatment for Duchenne Muscular Dystrophy (DMD)
  作者：Bharat Lagu、Arthur F. Kluge、Effie Tozzo、Ross Fredenburg、Eric L. Bell、Matthew M. Goddeeris、Peter Dwyer、Andrew Basinski、Ramesh S. Senaiar、Mahaboobi Jaleel、Nirbhay Kumar Tiwari、Sunil K. Panigrahi、Narasimha Rao Krishnamurthy、Taisuke Takahashi、Michael A. Patane

  DOI：10.1021/acsmedchemlett.8b00287

  日期：2018.9.13

  The X-ray structure of the previously reported PPAR delta modulator 1 bound to the ligand binding domain (LBD) revealed that the amide moiety in 1 exists in the thermodynamically disfavored cis-amide orientation. Isosteric replacement of the cis-amide with five-membered heterocycles led to the identification of imidazole 17 (MA-0204), a potent, selective PPAR delta modulator with good pharmacokinetic properties. MA-0204 was tested in vivo in mice and in vitro in patient derived muscle myoblasts (from Duchenne Muscular Dystrophy (DMD) patients); 17 altered the expression of PPAR delta target genes and improved fatty acid oxidation, which supports the therapeutic hypothesis for the study of MA-0204 in DMD patients.
• PPAR AGONISTS, COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
  申请人：Mitobridge, Inc.

  公开号：EP3359528B1

  公开（公告）日：2022-01-12