N-methyl-N-phenyl-2-<(5-hydroxy)methylindole> carboxamide | 160153-66-2

• 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-methyl-N-phenyl-2-<(5-hydroxy)methylindole> carboxamide
• 英文别名: 5-Hydroxy-N,1-dimethyl-N-phenyl-1H-indole-2-carboxamide；5-hydroxy-N,1-dimethyl-N-phenylindole-2-carboxamide
• CAS: 160153-66-2
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: OURSOMLIIYDTJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-methyl-N-phenyl-5-(3-methoxymethyl)indole-2-carboxamide 在 三氯化铝 、 苄硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以70%的产率得到N-methyl-N-phenyl-2-<(5-hydroxy)methylindole> carboxamide
  参考文献：
  名称：

  Functionalisation of the alkoxy group of alkyl aryl ethers. Demethylation, alkylthiolation and reduction of 5-methoxyindoles

  摘要：

  In the presence of AlX(3)-RSH three kinds of reactions may take place with 5-methoxy indoles : demethylation, alkylthiolation and reduction. The two latter reactions have never been observed to the present, with such reagents. Considerable improvement in the selective demethylation was found when PhCH(2)SH replaced EtSH previously used in such transformations. Factors leading to selective alkylthiolations or reductions are shown and mechanisms are proposed to explain these new reactions.

  DOI：

  10.1016/s0040-4020(01)89350-9

文献信息

• Indoles substitués et les compositions pharmaceutiques qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0624575A1

  公开（公告）日：1994-11-17

  Composés de formule générale (I) :    dans laquelle : X représente O ou S, X' représente O, S ou H₂, et R₁, R₂, R₃ et R₄ sont tels que définis dans la description. Ces composés trouvent leur application en thérapeutique dans le traitement ou la prévention des affections dues ou reliées à des phénomènes de peroxydation et notamment les désordres ischémiques cérébraux, rénaux ou cardiaques et les maladies métaboliques notamment l'athérome et l'artériosclérose, ainsi que l'inflammation.

  通式(I)化合物： 其中 X 代表 O 或 S X' 代表 O、S 或 H₂、 且 R₁、R₂、R₃ 和 R₄ 如说明中所定义。 这些化合物可用于治疗或预防过氧化现象引起的或与之相关的疾病，特别是脑、肾或心脏缺血性疾病和代谢性疾病，尤其是动脉粥样硬化和动脉硬化，以及炎症。
• Functionalisation of the alkoxy group of alkyl aryl ethers. Demethylation, alkylthiolation and reduction of 5-methoxyindoles
  作者：Catherine Caubère、Paul Caubère、Pierre Renard、Jean-Guy Bizot-Espiart、Sandra Ianelli、Mario Nardelli、Brigitte Jamart-Grégoiref

  DOI：10.1016/s0040-4020(01)89350-9

  日期：1994.1

  In the presence of AlX(3)-RSH three kinds of reactions may take place with 5-methoxy indoles : demethylation, alkylthiolation and reduction. The two latter reactions have never been observed to the present, with such reagents. Considerable improvement in the selective demethylation was found when PhCH(2)SH replaced EtSH previously used in such transformations. Factors leading to selective alkylthiolations or reductions are shown and mechanisms are proposed to explain these new reactions.
• Novel Indole-2-carboxamide and Cycloalkeno[1,2-<i>b</i>]indole Derivatives. Structure−Activity Relationships for High Inhibition of Human LDL Peroxidation
  作者：Catherine Kuehm-Caubere、Paul Caubere、Brigitte Jamart-Gregoire、Anne Negre-Salvayre、Dominique Bonnefont-Rousselot、Jean-Guy Bizot-Espiard、Bruno Pfeiffer、Daniel-Henri Caignard、Béatrice Guardiola-Lemaitre、Pierre Renard

  DOI：10.1021/jm960542k

  日期：1997.4.1

  Series of indole-2-carboxamide and cycloalkeno[1,2-b]indole derivatives were synthesized and evaluated in order to determine the necessary structural requirements for a high inhibition of human LDL copper-induced peroxidation. Various modulations were systematically performed on the indole and cycloalkeno[1,2-b]indole nuclei as well as on the carboxamide moiety. The best compounds (3c, 3e, 7c, 7f, 7h, 7g, and 7o) are between 5 and 30 times more active than probucol itself. Two of these compounds (3c and 70) were selected for complementary in vitro and in vivo investigations, which have shown additional properties of interest for the treatment and the prevention of atherosclerosis injuries. Compound 3e was found to have some antiinflammatory properties while compound 70 was proved to protect endothelial cells from the direct cytotoxicity of oxidized LDL with some additional calcium channel blocking properties.