1-ethoxycarbonyl-4-nitromethyl-1,2,3,6-tetrahydropyridine | 106244-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-ethoxycarbonyl-4-nitromethyl-1,2,3,6-tetrahydropyridine
• 英文别名: ethyl 3,6-dihydro-4-(nitromethyl)-1(2H)-pyridinecarboxylate；ethyl 4-(nitromethyl)-3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 106244-74-0
• 化学式: C₉H₁₄N₂O₄
• 分子量: 214.221
• InChiKey: TUKFGLKKADZRBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-ethoxycarbonyl-4-nitromethyl-1,2,3,6-tetrahydropyridine 在 铁粉 、 氯化铵 作用下， 以 水 、 甲苯 为溶剂， 反应 6.0h， 以89%的产率得到乙基4-(氨基甲基)-3,6-二氢-1(2H)-吡啶羧酸酯
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of benzamide derivatives as selective 5-HT4 receptor agonists

  摘要：

  It is thought that selective 5-HT4 receptor agonists-such as 4-amino-5-chloro-2-metboxy-N-[1-(6-oxo-6-phenylhexyl)piperidin-4-ylmethyl]benzamide (2)-have the ability to enhance both upper and lower gastrointestinal motility without any significant adverse effects.Modification of 2 was performed. Variation of the piperidin-4-ylmethyl moiety of 2 led to a decrease in the binding affinity for the 5-HT4 receptor. Following conversion of the carbonyl group on the benzoyl part to a hydroxyl or sulfoxide group, the binding affinity for the 5-HT4 receptor was retained although the effect on defecation was reduced. Many of the 4-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamides that had a ether or sulfide moiety in the side-chain part at the 1-position of the piperidine exhibited high affinity for the 5-HT4 receptor.Among these, phenylthio 41c and benzylthio derivative 44 were selective 5-HT4 receptor agonists, and had a similar effect on defecation to compound 2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.016
• 作为产物：
  描述：

  N-乙氧羰基-4-哌啶酮 在 sodium ethanolate 、 phosphorus pentoxide 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.5h， 生成 1-ethoxycarbonyl-4-nitromethyl-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of benzamide derivatives as selective 5-HT4 receptor agonists

  摘要：

  It is thought that selective 5-HT4 receptor agonists-such as 4-amino-5-chloro-2-metboxy-N-[1-(6-oxo-6-phenylhexyl)piperidin-4-ylmethyl]benzamide (2)-have the ability to enhance both upper and lower gastrointestinal motility without any significant adverse effects.Modification of 2 was performed. Variation of the piperidin-4-ylmethyl moiety of 2 led to a decrease in the binding affinity for the 5-HT4 receptor. Following conversion of the carbonyl group on the benzoyl part to a hydroxyl or sulfoxide group, the binding affinity for the 5-HT4 receptor was retained although the effect on defecation was reduced. Many of the 4-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamides that had a ether or sulfide moiety in the side-chain part at the 1-position of the piperidine exhibited high affinity for the 5-HT4 receptor.Among these, phenylthio 41c and benzylthio derivative 44 were selective 5-HT4 receptor agonists, and had a similar effect on defecation to compound 2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.016

文献信息

• Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed
  申请人：Janssen Pharmaceutica N.V.

  公开号：US04689330A1

  公开（公告）日：1987-08-25

  Novel substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines useful as anti-depressives, in the treatment of Parkinson's disease and in the treatment of diseases related with disturbed enterokinesia.

  新型替代N-[(4-哌啶基)烷基]的环状氧唑和噻唑胺类化合物可用作抗抑郁药，在帕金森病的治疗以及与肠动力紊乱相关疾病的治疗中有用。
• Substituted N-[(4-piperidinyl)alkyl] bicyclic condensed ozazol- and thiazolamines
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0199400A2

  公开（公告）日：1986-10-29

  Novel substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol-and thiazolamines of formula wherein L is a radical or the pharmaceutically acceptable acid addition salts and possible stereochemically isomeric forms thereof, which compounds have anti-depressive, anti-Parkinson and enterokinetic activity; pharmaceutical compositions containing such compounds as an active ingredient and methods of preparing said compounds and pharmaceutical compositions.

  式中的新型取代 N-[(4-哌啶基)烷基]双环缩合噁唑和噻唑胺 其中 L 是自由基 或 药学上可接受的酸加成盐及其可能的立体化学异构形式，这些化合物具有抗抑郁、抗帕金森和肠动力活性；含有这些化合物作为活性成分的药物组合物以及制备所述化合物和药物组合物的方法。
• US4689330A
  申请人：——

  公开号：US4689330A

  公开（公告）日：1987-08-25
• US4749702A
  申请人：——

  公开号：US4749702A

  公开（公告）日：1988-06-07
• US4826848A
  申请人：——

  公开号：US4826848A

  公开（公告）日：1989-05-02