N-(adamantan-1-yl)-[1,1′-biphenyl]-4-carboxamide | 313373-25-0

• 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-(adamantan-1-yl)-[1,1′-biphenyl]-4-carboxamide
• 英文别名: N-(adamantan-1-yl)-[1,1‘-biphenyl]-4-carboxamide；N-(1-adamantyl)-4-phenylbenzamide
• CAS: 313373-25-0
• 化学式: C₂₃H₂₅NO
• 分子量: 331.458
• InChiKey: YNLIWSUCYOIHQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对三氟甲基苯胺 、 N-(adamantan-1-yl)-[1,1′-biphenyl]-4-carboxamide 在 Cp*Ir(OAc)₂ 、 copper diacetate 、 双三氟甲烷磺酰亚胺银盐 作用下， 反应 3.0h， 以56%的产率得到4-adamantyl-N-butyl-2-(4-(trifluoromethyl)phenylamino)benzamide
  参考文献：
  名称：

  Iridium-Catalyzed C–H Amination with Anilines at Room Temperature: Compatibility of Iridacycles with External Oxidants

  摘要：

  Described herein is the development of an iridium-catalyzed direct C-H amination of benzamides with anilines at room temperature, representing a unique example of an Ir catalyst system that is compatible with external oxidants. Mechanistic details, such as the isolation and characterization of key iridacycle intermediates, are also discussed.

  DOI：

  10.1021/ja502270y
• 作为产物：
  描述：

  盐酸金刚烷胺 、 4-苯基苯甲酸 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 四氢呋喃 为溶剂， 反应 1.0h， 以62%的产率得到N-(adamantan-1-yl)-[1,1′-biphenyl]-4-carboxamide
  参考文献：
  名称：

  人瞬态受体潜在阳离子通道亚家族M成员8通道的新型联苯酰胺拮抗剂的基于结构的设计，在感觉神经病的治疗中具有潜在的意义。

  摘要：

  报道的基于薄荷醇的瞬时受体潜在阳离子通道亚家族M成员8通道（TRPM8）拮抗剂的结构活性关系研究，在计算模拟和基于结构的设计的指导下，发现了一系列新的TRPM8拮抗剂，其选择性> 10倍。相关的TRP亚型。Spiro [4.5] decan-8-yl类似物14抑制伊西林诱发的Ca2 +进入稳定表达人TRPM8（hTRPM8）的HEK-293细胞，IC50为2.4±1.0 nM，而在全细胞膜片钳记录中，该类似物抑制薄荷醇诱发的电流，hTRPM8 IC50为64±2 nM。在我们的hTRPM8同源模型中，化合物14的分子动力学（MD）模拟表明，该拮抗剂在正构位点内形成广泛的疏水性接触。在湿狗摇（WDS）分析中，化合物14剂量依赖性地阻断了西西林触发的小鼠摇动行为。局部给药后，化合物14剂量依赖性地抑制微克剂量的周围神经病的鼠模型中由化学疗法奥沙利铂引起的感性异常性疼痛。我们的发现表明，我们系列

  DOI：

  10.1021/acschemneuro.9b00404

文献信息

• Iridium-Catalyzed Direct C–H Amination with Alkylamines: Facile Oxidative Insertion of Amino Group into Iridacycle
  作者：Hyunwoo Kim、Sukbok Chang

  DOI：10.1021/acscatal.5b02165

  日期：2015.11.6

  Described herein is the development of Cp*Ir-(III)-catalyzed direct arene C-H amination using alkylamines as an amino source. This C-N bond formation showcases a notable example of cross-dehydrogenative coupling to install an amino functionality at the ortho-position of benzamide substrates. Mechanistic studies including the isolation of an amine-bound iridacyclic intermediate along with a set of chemical oxidations demonstrated the Ir-catalyzed inner-sphere C-H amination with primary alkylamines for the first time.
• [EN] TRANSIENT RECEPTOR POTENTIAL MELASTATIN 8 (TRPM8) ANTAGONISTS AND RELATED METHODS<br/>[FR] ANTAGONISTES DU MELASTATIN POTENTIEL DE RÉCEPTEUR TRANSITOIRE 8 (TRPM8) ET MÉTHODES ASSOCIÉES
  申请人：MARSHALL UNIV RESEARCH CORPORATION

  公开号：WO2020160464A1

  公开（公告）日：2020-08-06

  A TRPM8 antagonist is provided that comprises the following the formula (I) described herein. In the formula (I), R1 is selected from a cycloalkyl, a bicycloalkyl, or a tricycloalkyl group. Each R1 group has 5 to 12 carbon atoms. Further, each R1 group is optionally substituted with an alkyl group having 1 to 5 carbons atoms or with a cycloalkyl group having 4 to 12 carbon atoms, and each R1 group is optionally saturated or partially unsaturated. Methods for treating pain are further provided and comprise administering to a subject in need thereof an effective amount of a TRPM8 antagonist comprising the formula (I).
• Structure-Based Design of Novel Biphenyl Amide Antagonists of Human Transient Receptor Potential Cation Channel Subfamily M Member 8 Channels with Potential Implications in the Treatment of Sensory Neuropathies
  作者：V. Blair Journigan、Zhiwei Feng、Saifur Rahman、Yuanqiang Wang、A. R. M. Ruhul Amin、Colleen E. Heffner、Nicholas Bachtel、Siyi Wang、Sara Gonzalez-Rodriguez、Asia Fernández-Carvajal、Gregorio Fernández-Ballester、Jacob K. Hilton、Wade D. Van Horn、Antonio Ferrer-Montiel、Xiang-Qun Xie、Taufiq Rahman

  DOI：10.1021/acschemneuro.9b00404

  日期：2020.2.5

  dose-dependently blocks icilin-triggered shaking behaviors in mice. Upon local administration, compound 14 dose dependently inhibits cold allodynia evoked by the chemotherapy oxaliplatin in a murine model of peripheral neuropathy at microgram doses. Our findings suggest that 14 and other biphenyl amide analogues within our series can find utility as potent antagonist chemical probes derived from (-)-menthol

  报道的基于薄荷醇的瞬时受体潜在阳离子通道亚家族M成员8通道（TRPM8）拮抗剂的结构活性关系研究，在计算模拟和基于结构的设计的指导下，发现了一系列新的TRPM8拮抗剂，其选择性> 10倍。相关的TRP亚型。Spiro [4.5] decan-8-yl类似物14抑制伊西林诱发的Ca2 +进入稳定表达人TRPM8（hTRPM8）的HEK-293细胞，IC50为2.4±1.0 nM，而在全细胞膜片钳记录中，该类似物抑制薄荷醇诱发的电流，hTRPM8 IC50为64±2 nM。在我们的hTRPM8同源模型中，化合物14的分子动力学（MD）模拟表明，该拮抗剂在正构位点内形成广泛的疏水性接触。在湿狗摇（WDS）分析中，化合物14剂量依赖性地阻断了西西林触发的小鼠摇动行为。局部给药后，化合物14剂量依赖性地抑制微克剂量的周围神经病的鼠模型中由化学疗法奥沙利铂引起的感性异常性疼痛。我们的发现表明，我们系列
• Iridium-Catalyzed C–H Amination with Anilines at Room Temperature: Compatibility of Iridacycles with External Oxidants
  作者：Hyunwoo Kim、Kwangmin Shin、Sukbok Chang

  DOI：10.1021/ja502270y

  日期：2014.4.23

  Described herein is the development of an iridium-catalyzed direct C-H amination of benzamides with anilines at room temperature, representing a unique example of an Ir catalyst system that is compatible with external oxidants. Mechanistic details, such as the isolation and characterization of key iridacycle intermediates, are also discussed.