N-{2-[(3-methoxyphenyl)phenylamino]ethyl}butanamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-{2-[(3-methoxyphenyl)phenylamino]ethyl}butanamide
• 英文别名: N-{2-[(3-methoxyphenyl)-phenylamino]ethyl}butanamide；N-[2-(N-(3-methoxyphenyl)anilino)ethyl]butanamide
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: MBOGNCNDFYBDJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丁酸酐 、 3-[(3-methoxyphenyl)methylamino]propionitrile 在 镍 氢气 作用下， 以 四氢呋喃 为溶剂， 60.0 ℃ 、405.33 kPa 条件下， 反应 5.0h， 以80%的产率得到N-{2-[(3-methoxyphenyl)phenylamino]ethyl}butanamide
  参考文献：
  名称：

  N-（取代的苯胺基乙基）酰胺：一类新型褪黑激素受体配体的设计，合成和药理学表征。

  摘要：

  提出了一系列新型的褪黑激素受体配体，其特征在于N-（取代的苯胺基乙基）酰胺基支架，以及初步的结构-活性关系（SAR）。通过在苯胺氮，苯环和酰胺侧链上引入不同的取代基，可以调节MT1和MT2受体的结合亲和力和内在活性。通过应用先前开发的SAR模型已经实现了新合成化合物的固有活性和MT2选择性的调节，从而提供了具有不同结合和固有活性特征的化合物。具有庞大的ss-萘基的化合物3d表现为具有亚nM亲和力的MT2选择性拮抗剂。如在非选择性N-甲基-苯胺基激动剂3i中那样，取代基的尺寸减小增强了内在活性。

  DOI：

  10.1021/jm700957j
• 作为试剂：
  描述：

  N-{2-[(3-methoxyphenyl)phenylamino]ethyl}acetamide 、 、 丁酸酐 在 N-{2-[(3-methoxyphenyl)phenylamino]ethyl}butanamide 作用下， 以Yield (5n)的产率得到N-{2-[(3-methoxyphenyl)phenylamino]ethyl}butanamide
  参考文献：
  名称：

  Melatonin ligands having antidepressant activity as well as sleep inducing properties

  摘要：

  公式I的新型褪黑素配体：或其药学上可接受的盐，其中：n为1或2；m为0、1或2；p为0、1、2、3、4、5、6、7或8；v为2或3；A为芳基或杂环芳基；Z为O、S或NR8；Y选自氢、芳基、杂环芳基、C1-C6烷基、C3-C6环烷基和R，其中R选自氢、羟基、—OCF3、CF3、C1-C8烷基、C1-C8烷氧基、C1-C8烷硫基、卤素和—Z—（CH2）p-A；R1选自C1-C4烷基、C3-C6环烷基、CF3、羟基取代的C1-C4烷基、羟基取代的C3-C8环烷基和NHR5，其中R5为C1-C3烷基或C3-C6环烷基；R2选自氢、C1-C4烷基、C1-C4烷氧基、OCF3、CF3、羟基和卤素；R3选自氢、C1-C4烷基、C1-C4烷氧基、OCF3、CF3、羟基和卤素；R和R3可连接在一起形成一个—O—（CH2）v桥，代表它们附着的碳原子形成一个5-或6-成员的杂环环系；R4选自氢、C1-C4烷基、C1-C4烷氧基、OCF3、CF3、羟基和卤素；R6选自氢和C1-C6烷基；R7选自氢、C1-C4烷基、C1-C4烷氧基、OCF3、CF3、羟基和卤素；R8选自氢和C1-C4烷基。

  公开号：

  US08791163B2

文献信息

• [EN] METHODS AND USES OF MELATONIN LIGANDS<br/>[FR] PROCÉDÉS ET UTILISATIONS DE LIGANDS DE TYPE MÉLATONINE
  申请人：GOBBI GABRIELLA

  公开号：WO2015021535A1

  公开（公告）日：2015-02-19

  The disclosure provides methods and uses for alleviating and/or treating pain including pain disorders using melatonin ligands of Formula I: or pharmaceutically acceptable salts thereof wherein: n is 1 or 2; m is 0, 1 or 2; p is 0, 1, 2, 3, 4, 5, 6, 7 or 8; v is 2 or 3; A is aryl or heteroaryl; Z is 0, S or NR8; Y is chosen from hydrogen, aryl, heteroaryl, C1-C6 alkyl, C3-C6 cycloalkyl, and R is chosen from hydrogen, hydroxyl, -OCF3, CF3, C1-C8 alkyl, C1-C8 alkyloxy, C1-C8 alkylthio, halogen and -Z-(CH2)P-A; R1 is chosen from C1-C4 alkyl, C3-C6 cycloalkyl, CF3, hydroxy- substituted C1-C4 alkyl, hydroxy-substituted C3-C6 cycloalkyl, and NHR5, wherein R5 is H, C1-C3 alkyl or C3-C6 cycloalkyl; R2 is chosen from hydrogen, C1-C4 alkyl, C1-C4 alkyloxy, OCF3, CF3, hydroxyl, and halogen; R3 is chosen from hydrogen, C1-C4 alkyl, C1-C4 alkyloxy, OCF3, CF3, hydroxyl and halogen; R and R3 may be connected together to form an -0-(CH2)v bridge representing with the carbon atoms to which they are attached a 5- or 6-membered heterocyclic ring system; R4 is chosen from hydrogen, C1-C4 alkyl, C1-C4 alkyloxy, OCF3, CF3, hydroxyl, and halogen; R6 is chosen from hydrogen and C1-C4 alkyl; R7 is chosen from hydrogen, C1-C4 alkyl, C1-C4 alkyloxy, OCF3, CF3, hydroxyl and halogen; and R8 is chosen from hydrogen and C1-C4 alkyl.

  本文提供了使用公式I中的褪黑素配体或其药学上可接受的盐来缓解和/或治疗疼痛，包括疼痛性疾病的方法和用途，其中：n为1或2；m为0、1或2；p为0、1、2、3、4、5、6、7或8；v为2或3；A为芳基或杂环芳基；Z为0、S或NR8；Y选自氢、芳基、杂环芳基、C1-C6烷基、C3-C6环烷基，R选自氢、羟基、-OCF3、CF3、C1-C8烷基、C1-C8烷氧基、C1-C8烷硫基、卤素和-Z-(CH2)P-A；R1选自C1-C4烷基、C3-C6环烷基、CF3、羟基取代的C1-C4烷基、羟基取代的C3-C6环烷基和NHR5，其中R5为H、C1-C3烷基或C3-C6环烷基；R2选自氢、C1-C4烷基、C1-C4烷氧基、OCF3、CF3、羟基和卤素；R3选自氢、C1-C4烷基、C1-C4烷氧基、OCF3、CF3、羟基和卤素；R和R3可以连接在一起形成一个-0-(CH2)v桥，代表它们附着的碳原子形成一个5-或6-成员杂环环系；R4选自氢、C1-C4烷基、C1-C4烷氧基、OCF3、CF3、羟基和卤素；R6选自氢和C1-C4烷基；R7选自氢、C1-C4烷基、C1-C4烷氧基、OCF3、CF3、羟基和卤素；R8选自氢和C1-C4烷基。
• NOVEL MELATONIN LIGANDS HAVING ANTIDEPRESSANT ACTIVITY AS WELL AS SLEEP INDUCING PROPERTIES
  申请人：Gobbi Gabriella

  公开号：US20100267836A1

  公开（公告）日：2010-10-21

  Novel melatonin ligands of Formula I: or pharmaceutically acceptable salts thereof wherein: n is 1 or 2; m is 0, 1 or 2; p is 0, 1, 2, 3, 4, 5, 6, 7 or 8; v is 2 or 3; A is aryl or heteroaryl; Z is O, S or NR 8 ; Y is selected from the group consisting of hydrogen, aryl, heteroaryl, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, and R is selected from the group consisting of hydrogen, hydroxyl, —OCF 3 , CF 3 , C 1 -C 8 alkyl, C 1 -C 8 alkyloxy, C 1 -C 8 alkylthio, halogen and —Z—(CH 2 ) p -A; R 1 is selected from the group consisting of C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, CF 3 , hydroxy-substituted C 1 -C 4 alkyl, hydroxy-substituted C 3 -C 8 cycloalkyl, and NHR 5 , wherein R 5 is C 1 -C 3 alkyl or C 3 -C 6 cycloalkyl; R 2 is selected from the group consisting of: hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, OCF 3 , CF 3 , hydroxyl, and halogen; R 3 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, OCF 3 , CF 3 , hydroxyl, and halogen; R and R 3 may be connected together to form an —O—(CH 2 ) v bridge representing with the carbon atoms to which they are attached a 5 - or 6 -membered heterocyclic ring system; R 4 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, OCF 3 , CF 3 , hydroxyl, and halogen; R 6 is selected from the group consisting of hydrogen and C 1 -C 6 alkyl; R 7 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, OCF 3 , CF 3 , hydroxyl, and halogen; and R 8 is selected from the group consisting of hydrogen and C 1 -C 4 alkyl.

  化合物I的新型褪黑激素配体：或其药学上可接受的盐，其中：n为1或2；m为0，1或2；p为0，1，2，3，4，5，6，7或8；v为2或3；A为芳基或杂芳基；Z为O，S或NR8；Y选择自氢，芳基，杂芳基，C1-C6烷基，C3-C6环烷基和R，其中R选择自氢，羟基，—OCF3，CF3，C1-C8烷基，C1-C8烷氧基，C1-C8烷硫基，卤素和—Z—（CH2）p-A；R1选择自C1-C4烷基，C3-C6环烷基，CF3，羟基取代的C1-C4烷基，羟基取代的C3-C8环烷基和NHR5，其中R5为C1-C3烷基或C3-C6环烷基；R2选择自氢，C1-C4烷基，C1-C4烷氧基，OCF3，CF3，羟基和卤素；R3选择自氢，C1-C4烷基，C1-C4烷氧基，OCF3，CF3，羟基和卤素；R和R3可以连接形成—O—（CH2）v桥，表示与它们连接的碳原子一起形成5-或6-成员杂环环系；R4选择自氢，C1-C4烷基，C1-C4烷氧基，OCF3，CF3，羟基和卤素；R6选择自氢和C1-C6烷基；R7选择自氢，C1-C4烷基，C1-C4烷氧基，OCF3，CF3，羟基和卤素；R8选择自氢和C1-C4烷基。
• Novel elatonin ligands having antidepressant activity as well as sleep inducing properties
  申请人：McGill University

  公开号：EP1973868B1

  公开（公告）日：2015-09-09
• Methods and Uses of Melatonin Ligands
  申请人：DOMINGUEZ LOPEZ Sergio

  公开号：US20160221932A1

  公开（公告）日：2016-08-04

  The disclosure provides methods and uses for alleviating and/or treating pain including pain disorders using melatonin ligands of Formula I: or pharmaceutically acceptable salts thereof wherein: n is 1 or 2; m is 0, 1 or 2; p is 0, 1, 2, 3, 4, 5, 6, 7 or 8; v is 2 or 3; A is aryl or heteroaryl; Z is 0, S or NR 8 ; Y is chosen from hydrogen, aryl, heteroaryl, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, and R is chosen from hydrogen, hydroxyl, —OCF 3 , CF 3 , C 1 -C 8 alkyl, C 1 -C 8 alkyloxy, C 1 -C 8 alkylthio, halogen and —Z—(CH 2 p -A; R 1 is chosen from C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, CF 3 , hydroxy-substituted C 1 -C 4 alkyl, hydroxy-substituted C 3 -C 6 cycloalkyl, and NHR 5 , wherein R 5 is H, C 1 -C 3 alkyl or C 3 -C 6 cycloalkyl; R 2 is chosen from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, OCF 3 , CF 3 , hydroxyl, and halogen; R 3 is chosen from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, OCF 3 , CF 3 , hydroxyl and halogen; R and R 3 may be connected together to form an -0-(CH 2 ) v bridge representing with the carbon atoms to which they are attached a 5- or 6-membered heterocyclic ring system; R 4 is chosen from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, OCF 3 , CF 3 , hydroxyl, and halogen; R 6 is chosen from hydrogen and C 1 -C 4 alkyl; R 7 is chosen from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy, OCF 3 , CF 3 , hydroxyl and halogen; and R 8 is chosen from hydrogen and C 1 -C 4 alkyl.
• US8791163B2
  申请人：——

  公开号：US8791163B2

  公开（公告）日：2014-07-29