1-苄基-1,2,5,6-四氢吡啶-3-羧酸甲酯 | 88928-69-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 中文名称: 1-苄基-1,2,5,6-四氢吡啶-3-羧酸甲酯
• 英文名称: 1-benzyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
• 英文别名: 1-Benzyl-1,2,5,6-tetrahydro-pyridin-3-carbonsaeure-methylester；1-Benzyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester；methyl 1-benzyl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 88928-69-2
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: JVQXZYPGMNMHKE-UHFFFAOYSA-N

物化性质

• 沸点：
  327.6±30.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-苄基-1,2,5,6-四氢吡啶-3-羧酸甲酯 在 六甲基磷酰三胺 、 三乙酰氧基硼氢化钠 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 38.0h， 生成 (1-Benzyl-3-butyl-1,2,3,6-tetrahydro-pyridin-3-ylmethyl)-butyl-amine
  参考文献：
  名称：

  一种基于生物遗传学原理的马丹胺三环核心的方法。

  摘要：

  [反应：见正文]描述了一种简短合成的中间体，该中间体具有天然madangamines的三环核心，即海洋海绵中发现的生物活性生物碱。关键反应需要使二乙基丙酮二羧酸钠盐与二氢吡啶鎓盐衍生物缩合。这种新方法是基于将麦当胺与ircinals（一种在相同数量的海绵中存在的相关生物碱）相关联的生物遗传学提案进行建模的。

  DOI：

  10.1021/ol050740i
• 作为产物：
  描述：

  氢溴酸槟榔碱 在 1-氯乙基氯甲酸酯 、 碳酸氢钠 、 sodium carbonate 、 1,2-二氯乙烷 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 11.33h， 生成 1-苄基-1,2,5,6-四氢吡啶-3-羧酸甲酯
  参考文献：
  名称：

  N-Heteroarylmethyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid a novel scaffold for the design of uncompetitive α-glucosidase inhibitors

  摘要：

  The enzyme alpha-glucosidase has attracted interest owing to its involvement in the digestive process of carbohydrate, its role in intracellular glycoprotein trafficking, tumorigenesis and viral infection. In this study, several members of a new family of N-heteroarylmethyl substituted azasugars were synthesized and evaluated as alpha-glucosidase inhibitors. We systematically investigated the effect of different N-substituents as well as the role of hydroxyl and carboxylate moieties on the piperidine ring. The compounds N-heteroarylmethyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid emerged as potent alpha-glucosidase inhibitors. Unlike Acarbose and other clinically relevant alpha-glucosidase inhibitors, these compounds act through a reversible uncompetitive mechanism of inhibition which make them attractive candidates for drug development. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.012

文献信息

• Efficient Synthesis of Fused Bicyclic Glutarimides. Its Application to (±)-Alloyohimbane and Louisianin D
  作者：Hung-Wei Chen、Ru-Ting Hsu、Meng-Yang Chang、Nein-Chen Chang

  DOI：10.1021/ol060958k

  日期：2006.7.1

  [reaction: see text] The reaction of alpha-sulfonyl acetamide 1 with various cyclic unsaturated esters 2 to fused bicyclic glutarimides is reported. Syntheses of (+/-)-alloyohimbane (4) and louisianin D (5) have been accomplished.

  [反应：见正文]据报道，α-磺酰基乙酰胺1与各种环状不饱和酯2反应生成稠合的双环戊二酰亚胺。（+/-）-铝环戊烷（4）和路易宁D（5）的合成已完成。
• Compound
  申请人：AstraZeneca AB

  公开号：US20040087800A1

  公开（公告）日：2004-05-06

  The present invention relates to certain spirooxindole derivatives of the formula I, and pharmaceutically acceptable salts thereof, which exhibit good analgesic properties and are particularly effective in the treatment of chronic pain. 1

  本发明涉及公式I的某些螺环氧吲哚衍生物及其药学上可接受的盐，它们具有良好的镇痛性能，特别是在治疗慢性疼痛方面非常有效。
• Spirooxindole derivatives that act as analgesics
  申请人：AstraZeneca AB

  公开号：US06774132B1

  公开（公告）日：2004-08-10

  The present invention relates to certain spirooxindole derivatives and to pharmaceutically acceptable salts thereof, which exhibit good analgesic properties and are effective in the treatment of chronic pain. The derivatives have the structure of formula I: wherein: Ar is benzene or pyridine; X is NHCO—; —CONH—; or —NH—SO2—; Y is a single bond; and Z is —CH═CHCH2.

  本发明涉及某些螺环氧吲哚衍生物及其药学上可接受的盐，其表现出良好的镇痛性能并且在治疗慢性疼痛方面有效。这些衍生物具有以下结构式I： 其中：Ar是苯或吡啶；X是NHCO—；—CONH—；或—NH—SO2—；Y是单键；Z是—CH═CHCH2。
• Blood platelet aggregation inhibitory 1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid derivatives and salts thereof; pharmaceutical compositions thereof; and analogy processes for the manufacture thereof
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0011447A1

  公开（公告）日：1980-05-28

  The invention concerns novel 1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid derivates of the tormuta:- wherein R1 is hydroxy, amino, (1-4C)alkylamino, di-[(1-4C)alkyl]amino, benzyloxy optionally substituted by halogeno, or (1-6C)alkoxy optionally substituted by (1- '4C)alkoxy, morpholino or di-[(1-4C)alkyl]amino; and benzene ring A bears one or two substituents selected from halogeno, (1-4C)alkyl, cyano, carboxamido, trifluoromethyl and hydroxy; and their pharmaceutically acceptable salts; together with pharmaceutical compositions thereof; and analogy processes for their manufacture. The compounds of formula I are inhibitors of the aggregation of blood platelets and may be of application in the treatment or prophylaxis of thrombosis or occlusive vascular disease. A representative compound of the invention is 1-(2-chlorobenzyl)-1,2,5,6-tetrahydropyridine -3-carboxylic acid.

  本发明涉及新型 1-苄基-1,2,5,6-四氢吡啶-3-羧酸衍生物，其结构式为：- 1-苄基-1,2,5,6-四氢吡啶-3-羧酸衍生物 其中 R1 是羟基、氨基、(1-4C)烷基氨基、二[(1-4C)烷基]氨基、任选被卤素取代的苄氧基或任选被(1-'4C)烷氧基取代的(1-6C)烷氧基、吗啉基或二[(1-4C)烷基]氨基；和苯环 A 带有一个或两个选自卤素、(1-4C)烷基、氰基、羧酰胺基、三氟甲基和羟基的取代基；及其药学上可接受的盐；连同其药物组合物；以及类比的制造工艺。 式 I 的化合物是血小板聚集的抑制剂，可用于治疗或预防血栓形成或闭塞性血管疾病。本发明的代表性化合物是 1-(2-氯苄基)-1,2,5,6-四氢吡啶-3-羧酸。
• Analgesic spiroindole derivatives
  申请人：AstraZeneca AB

  公开号：EP1426375A2

  公开（公告）日：2004-06-09

  The present invention relates to certain spirooxindole derivatives of the formula I, and pharmaceutically acceptable salts thereof, which exhibit good analgesic properties and are particularly effective in the treatment of chronic pain.

  本发明涉及某些式 I 的螺氧化吲哚衍生物及其药学上可接受的盐类，它们具有良好的镇痛特性，对治疗慢性疼痛特别有效。