2-(4-hydroxy-3-nitrophenyl)-N,N-dipropylacetamide | 101389-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-hydroxy-3-nitrophenyl)-N,N-dipropylacetamide
• 英文别名: N,N-dipropyl-(4-hydroxy-3-nitrophenyl)-acetamide；N,N-dipropyl-(4-hydroxy-3-nitrophenyl)acetamide；N,N-dipropyl-(4-hydroxy-3-nitrophenyl) acetamide
• CAS: 101389-55-3
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: GFHQSRIMUNIWRS-UHFFFAOYSA-N

物化性质

• 熔点：
  63-65 °C
• 沸点：
  436.2±35.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxy-3-nitrophenyl)-N,N-dipropylacetamide 生成 2-(4-甲氧基-3-硝基苯基)-N,N-二丙基乙胺盐酸盐
  参考文献：
  名称：

  STRINGER, O.;WEINSTOCK, J.

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-3-硝基苯乙酸 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 3.5h， 生成 2-(4-hydroxy-3-nitrophenyl)-N,N-dipropylacetamide
  参考文献：
  名称：

  Synthesis and evaluation of non-catechol D-1 and D-2 dopamine receptor agonists: benzimidazol-2-one, benzoxazol-2-one, and the highly potent: benzothiazol-2-one 7-ethylamines

  摘要：

  Our interest in identifying D-1 and D-2 dopamine receptor agonists that are not catechols led us to extend previous studies with oxindoles by investigating analogues of dopamine, N,N-dipropyldopamine, m-tyramine, N,N-dipropyl-m-tyramine, and epinine in which the m-hydroxyl is replaced by the NH portion of a thiazol-2-one, oxazol-2-one, or imidazol-2-one group fused to the 2,3-position. These compounds were evaluated for their affinity and agonist activity at D-1 and D-2 receptors by using in vitro assays. Replacement of the m-hydroxy in N,N-dipropyldopamine with the thiazol-2-one group resulted in a dramatic increase in D-2 receptor affinity and activity compared to that of N,N-dipropyldopamine itself or that of the corresponding oxindole, 1. The resulting compound, 7-hydroxy-4-[2-(di-n-propylamino)ethyl]benzothiazol-2(3H)-one (4), is the most potent D-2 receptor agonist reported to date in the field-stimulated rabbit ear artery (ED50 = 0.028 nM). The benzoxazol-2-one (6), benzimidazol-2-one (5), and isatin (51) analogues showed D-2 receptor agonist potency similar to that of 1. The des-7-hydroxyl analogue of 4 (21) also has enhanced D-2 receptor activity compared to that of the corresponding oxindole, 8. 7-Hydroxy-4-(2-aminoethyl)benzothiazol-2(3H)-one, 27, a non-catechol, has enhanced D-1 and D-2 receptor activity in vitro compared to that of the corresponding oxindole, 7. In vivo, 27 increased renal blood flow and decreased blood pressure in the dog. However, these effects were mediated primarily by D-2 receptor agonist activity. This may be a result of the D-1 partial agonist activity of 27 coupled with its potent D-2 receptor activity.

  DOI：

  10.1021/jm00390a009

文献信息

• Melanin-concentrating hormone antagonist
  申请人：——

  公开号：US20030158177A1

  公开（公告）日：2003-08-21

  A melanin-concentrating hormone antagonist comprising a compound of the formula: 1 wherein R is hydrogen atom or a cyclic group which may be substituted; X is a bond or a spacer having a main chain of 1 to 10 atoms; Y is a spacer having a main chain of 1 to 6 atoms; ring A is benzene ring which may be further substituted; ring B is a 5- to 9-membered nitrogen-containing non-aromatic heterocyclic ring which may be further substituted; R 1 and R 2 are the same or different and are hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted; or R 1 and R 2 , together with the adjacent nitrogen atom, may form a nitrogen-containing heterocyclic ring which may be substituted; or R 2 , together with the adjacent nitrogen atom and Y, may form a nitrogen-containing heterocyclic ring which may be substituted; or a salt thereof is useful as a preventive or therapeutic agent for obesity, etc.

  一种黑素浓缩激素拮抗剂，包括以下结构的化合物：其中R是氢原子或可能被取代的环状基团；X是具有1到10个原子主链的键或间隔物；Y是具有1到6个原子主链的间隔物；环A是苯环，可能进一步被取代；环B是一个含氮的非芳香杂环环，成员数为5到9，可能进一步被取代；R1和R2相同或不同，是氢原子、可能被取代的烃基或可能被取代的杂环基；或者R1和R2，与相邻的氮原子一起，可以形成一个可能被取代的含氮杂环环；或者R2，与相邻的氮原子和Y一起，可以形成一个可能被取代的含氮杂环环；或其盐可用作肥胖等疾病的预防或治疗剂。
• 7-[2-(Dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0175525A1

  公开（公告）日：1986-03-26

  Compounds of the formula: and pharmaceutically acceptable salts are described in which: R is hydrogen, methyl or C2-6-alkanoyl; and R1 and R2 are, each, C1-6-alkyl, benzyl, phenethyl, methoxyphenethyl, hydroxyphenethyl or C2-6-alkanoyloxyphen- ethyl. The compounds are D2-dopamine agonists and have anti-hypertensive activity. Pharmaceutical compositions and methods of use are described, as are processes for their preparation.

  式中的化合物： 及药学上可接受的盐类，其中 R 是氢、甲基或 C2-6-烷酰基；以及 R1和R2各自为C1-6-烷基、苄基、苯乙基、甲氧基苯乙基、羟基苯乙基或C2-6-烷酰氧基苯乙基。 这些化合物是 D2-多巴胺激动剂，具有抗高血压活性。本文介绍了药物组合物和使用方法以及制备工艺。
• MELANIN-CONCENTRATING HORMONE ANTAGONIST
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1283199A1

  公开（公告）日：2003-02-12

  A melanin-concentrating hormone antagonist comprising a compound of the formula: wherein R is hydrogen atom or a cyclic group which may be substituted; X is a bond or a spacer having a main chain of 1 to 10 atoms; Y is a spacer having a main chain of 1 to 6 atoms; ring A is benzene ring which may be further substituted; ring B is a 5- to 9-membered nitrogen-containing non-aromatic heterocyclic ring which may be further substituted; R1 and R2 are the same or different and are hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted; or R1 and R2, together with the adjacent nitrogen atom, may form a nitrogen-containing heterocyclic ring which may be substituted; or R2, together with the adjacent nitrogen atom and Y, may form a nitrogen-containing heterocyclic ring which may be substituted; or a salt thereof is useful as a preventive or therapeutic agent for obesity, etc.

  一种黑色素浓缩激素拮抗剂，包括式中化合物： 其中 R 是氢原子或可被取代的环状基团；X 是主链为 1 至 10 个原子的键或间隔物；Y 是主链为 1 至 6 个原子的间隔物；环 A 是可被进一步取代的苯环；环 B 是可被进一步取代的 5 至 9 元含氮非芳香杂环；R1和R2相同或不同，且为氢原子、可被取代的烃基或可被取代的杂环基；或R1和R2连同相邻的氮原子可形成可被取代的含氮杂环；或R2连同相邻的氮原子和Y可形成可被取代的含氮杂环；或其盐可用作肥胖症等的预防或治疗剂。
• STRINGER, O. D.;WEINSTOCK, J.
  作者：STRINGER, O. D.、WEINSTOCK, J.

  DOI：——

  日期：——
• STRINGER, O.;WEINSTOCK, J.
  作者：STRINGER, O.、WEINSTOCK, J.

  DOI：——

  日期：——