N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)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-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)benzamide
• 英文别名: N-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]benzamide；N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]benzamide
• 化学式: C₁₆H₁₁F₆NO₂
• 分子量: 363.259
• InChiKey: QYOBPISPXIUKPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯胺 在 对甲苯磺酸 、 三乙胺 作用下， 以 水 、 甲苯 为溶剂， 生成 N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)benzamide
  参考文献：
  名称：

  Synthesis and inhibitory activity on hepatitis C virus RNA replication of 4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)aniline analogs

  摘要：

  Using our recently developed assay system for full-genome-length hepatitis C virus (HCV) RNA replication in human hepatoma-derived Li23 cells (ORL8), we identified 4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)aniline analog 1a as a novel HCV inhibitor. Structural modifications of 1a provided a series of sulfonamides 7 with much more potent HCV RNA replication-inhibitory activity than ribavirin. Compound 7a showed an additive anti-HCV effect in combination with standard anti-HCV therapy (IFN-α plus ribavirin). Since 7a generated reactive oxygen species (ROS) in the ORL8 system and its anti-HCV activity was blocked by vitamin E, its anti-HCV activity may be mediated at least in part by ROS.

  DOI：

  10.1016/j.bmcl.2014.07.019

文献信息

• [EN] MODULATORS OF THE RETINOIC ACID RECEPTOR-RELATED ORPHAN RECEPTORS<br/>[FR] MODULATEURS DES RÉCEPTEURS ORPHELINS LIÉS AU RÉCEPTEUR DE L'ACIDE RÉTINOÏQUE
  申请人：GRIFFIN PATRICK R

  公开号：WO2011115892A1

  公开（公告）日：2011-09-22

  The invention provides small molecule modulators of retinoic acid receptor-related orphan receptors such as RORα RORβ, or RORγ. Compounds of the invention can be effective modulators at concentrations ineffective to act on LXR receptors, or on other nuclear receptors, or other biological targets. Methods of modulation the RORs and methods of treating metabolic disorders, immune disorders, cancer, and CNS disorders wherein modulation of an ROR is medically indicated are also provided.

  这项发明提供了调节视黄酸受体相关孤儿受体的小分子调节剂，如RORα、RORβ或RORγ。该发明的化合物可以在无法对LXR受体或其他核受体或其他生物靶点产生作用的浓度下起到有效的调节作用。还提供了调节RORs的方法以及治疗代谢紊乱、免疫紊乱、癌症和中枢神经系统紊乱的方法，其中调节ROR在医学上是指示的。
• Structure-based design of substituted hexafluoroisopropanol-arylsulfonamides as modulators of RORc
  作者：Benjamin P. Fauber、Gladys de Leon Boenig、Brenda Burton、Céline Eidenschenk、Christine Everett、Alberto Gobbi、Sarah G. Hymowitz、Adam R. Johnson、Marya Liimatta、Peter Lockey、Maxine Norman、Wenjun Ouyang、Olivier René、Harvey Wong

  DOI：10.1016/j.bmcl.2013.10.054

  日期：2013.12

  The structure-activity relationships of T0901317 analogs were explored as RORc inverse agonists using the principles of property- and structure-based drug design. An X-ray co-crystal structure of T0901317 and RORc was obtained and provided molecular insight into why T0901317 functioned as an inverse agonist of RORc; whereas, the same ligand functioned as an agonist of FXR, LXR, and PXR. The structural data was also used to design inhibitors with improved RORc biochemical and cellular activities. The improved inhibitors possessed enhanced selectivity profiles (rationalized using the X-ray crystallographic data) against other nuclear receptors.
• [EN] CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS FOR MODULATING TRPV1<br/>[FR] CERTAINS TYPES D'ENTITES CHIMIQUES, COMPOSITIONS ET METHODE DE MODULATION DE TRPV1
  申请人：AMPHORA DISCOVERY CORP

  公开号：WO2007067619A2

  公开（公告）日：2007-06-14

  [EN] Provided are chemical entities chosen from compounds of Formula I and pharmaceutically or cosmetically acceptable salts, solvates, chelates, non-covalent complexes, prodrugs, and mixtures thereof. The chemical entities modulate TRPV1and are useful in the treatment of at least one disease or disorder modulated by TRPV1activity.
  [FR] L'invention porte sur des entités chimiques choisies parmi des composés de formule (I) et sur des sels acceptables d'un point de vue pharmaceutique ou cosmétique, des solvates, des chélates, des complexes non covalents, des promédicaments et des mélanges de ceux-ci. Les entités chimiques modulent TRPV1 et sont utiles dans le traitement d'au moins une maladie ou trouble modulé par l'activité de TRPV1.
• [EN] THERAPEUTIC AGENT FOR HEPATITIS C WHICH COMPRISES 4-(1,1,1,3,3,3-HEXAFLUORO-2-HYDROXYPROPAN-2-YL)BENZENE DERIVATIVE<br/>[FR] AGENT THÉRAPEUTIQUE POUR L'HÉPATITE C QUI COMPREND UN DÉRIVÉ DE 4-(1,1,1,3,3,3-HEXAFLUORO-2-HYDROXYPROPAN-2-YL)BENZÈNE
  申请人：UNIV OKAYAMA NAT UNIV CORP

  公开号：WO2014148438A1

  公开（公告）日：2014-09-25

  　本発明は、Ｃ型肝炎ウイルス複製阻害剤、及び、Ｃ型肝炎ウイルス感染症を治療するための医薬の提供を目的とする。具体的には、本発明は、一般式（Ｉ）で表される４－（１，１，１，３，３，３－ヘキサフルオロ－２－ヒドロキシプロパン－２－イル）ベンゼン誘導体及びそれらの溶媒和物若しくはそれらの水和物を有効成分として含む、Ｃ型肝炎ウイルス複製阻害剤である。 ［式中、Ｒ１及びＲ２は、同一又は相異なって、水素、ハロゲン原子、炭素数１～６の直鎖状又は分岐したアルキル基、炭素数１～６の直鎖状又は分岐したアルコキシ基、トリフルオロメチル基を表し、ＡはＮＲ３ＣＯ基、ＮＲ３ＳＯ２基、ＮＲ３ＣＯＮＨ基、ＮＲ３ＣＨ２基を表し、Ｒ３は、水素、あるいは、炭素数１～６の直鎖状又は分岐したアルキル基を表し、また、Ｒ３は左ベンゼン環と結合して５～７角形を形成しても良い。］
• Synthesis and inhibitory activity on hepatitis C virus RNA replication of 4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)aniline analogs
  作者：Kenji Matsuno、Youki Ueda、Miwa Fukuda、Kenji Onoda、Minoru Waki、Masanori Ikeda、Nobuyuki Kato、Hiroyuki Miyachi

  DOI：10.1016/j.bmcl.2014.07.019

  日期：2014.9

  Using our recently developed assay system for full-genome-length hepatitis C virus (HCV) RNA replication in human hepatoma-derived Li23 cells (ORL8), we identified 4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)aniline analog 1a as a novel HCV inhibitor. Structural modifications of 1a provided a series of sulfonamides 7 with much more potent HCV RNA replication-inhibitory activity than ribavirin. Compound 7a showed an additive anti-HCV effect in combination with standard anti-HCV therapy (IFN-α plus ribavirin). Since 7a generated reactive oxygen species (ROS) in the ORL8 system and its anti-HCV activity was blocked by vitamin E, its anti-HCV activity may be mediated at least in part by ROS.