N-{2-[(3-butoxyphenyl)(methylamino)]ethyl}acetamide | 944285-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-{2-[(3-butoxyphenyl)(methylamino)]ethyl}acetamide
• 英文别名: N-[2-(3-butoxy-N-methylanilino)ethyl]acetamide
• CAS: 944285-38-5
• 化学式: C₁₅H₂₄N₂O₂
• 分子量: 264.368
• InChiKey: BTJYTGMZHGTHJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  N-{2-[(3-methoxyphenyl)(methyl)amino]ethyl}acetamide 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 18.08h， 生成 N-{2-[(3-butoxyphenyl)(methylamino)]ethyl}acetamide
  参考文献：
  名称：

  MT1选择性褪黑激素受体配体：N-{[（（3-O-取代）苯胺基]烷基}酰胺的合成，药理学评估和分子动力学研究

  摘要：

  由于对MT 1亚型选择性具有选择性的结构特征的了解有限，因此对MT 1褪黑激素受体具有选择性的化合物的设计仍然是一项艰巨的任务，迄今仅报道了很少的选择性化合物。N-（苯胺基烷基）酰胺是一类多用途的褪黑激素受体配体，包括非选择性MT 1 / MT 2激动剂和MT 2选择性拮抗剂。我们合成了一系列新的N-（苯胺基烷基）酰胺，在苯胺环上带有3-芳基烷氧基或3-烷氧基取代基，以寻找新的强力和MT 1选择性配体。为了评估取代基大小和形状对结合亲和力和内在活性的影响，制备了柔性和构象受限的衍生物。的苯基丁氧基取代基，得到最好的结果，提供部分激动剂4，它被赋予高MT 1的结合亲和力（第ķ我= 8.93）和78倍的选择性为MT 1受体。为了研究对于激动剂识别的分子基础，并解释所述3-芳基烷氧基取代基的作用，我们建立了MT的同源模型1受体基于所述β 2在其激活状态下肾上腺素能受体的晶体结构。MT 1的绑定模

  DOI：

  10.1002/cmdc.201200303

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