N-Adamantan-1-yl-2-hydroxy-2-phenyl-acetamide | 120282-84-0

• 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-2-hydroxy-2-phenyl-acetamide
• 英文别名: N-(1-adamantyl)-2-hydroxy-2-phenylacetamide
• CAS: 120282-84-0
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: DXJXOHXGELNKQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Acetic acid (adamantan-1-ylcarbamoyl)-phenyl-methyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以99%的产率得到N-Adamantan-1-yl-2-hydroxy-2-phenyl-acetamide
  参考文献：
  名称：

  Anti-inflammatory Properties of New Adamantane Derivatives. Design, Synthesis, and Biological Evaluation

  摘要：

  A series of adamantane-containing molecules consisting of two lipophilic centers which are linked by different bridges (oxime esters, oxime ethers, amides, and symmetric alcohols), were designed and synthesized as anti-inflammatory agents. Their anti-inflammatory activity was evaluated as their ability to inhibit phlogistic-induced mouse paw edema. Some of the tested compounds exhibited activity comparable to that of diclofenac, others had a weaker activity, while some oxime esters proved to enhance the inflammatory response. In all cases, activity was dose-dependent. The deacylated compound 10 was found to be the most active of the series, inhibiting inflammation due to Baker's yeast, the mechanism of which involves mainly the activation of lipoxygenase and/or complement systems, a property which is absent from most selective cyclooxygenase only inhibiting non-steroidal anti-inflammatory drugs (NSAIDs).

  DOI：

  10.1002/(sici)1521-4184(199802)331:2<72::aid-ardp72>3.0.co;2-e

文献信息

• Structural Determinants of Indole-2-carboxamides: Identification of Lead Acetamides with Pan Antimycobacterial Activity
  作者：Pankaj Bhattarai、Pooja Hegde、Wei Li、Pavan Kumar Prathipati、Casey M. Stevens、Lixinhao Yang、Hinman Zhou、Amit Pandya、Katie Cunningham、Jenny Grissom、Mariaelena Roman Sotelo、Melanie Sowards、Lilian Calisto、Christopher J. Destache、Sonia Rocha-Sanchez、James C. Gumbart、Helen I. Zgurskaya、Mary Jackson、E. Jeffrey North

  DOI：10.1021/acs.jmedchem.2c00352

  日期：2023.1.12