1,2,5,6-四氢吡啶-3-甲酸甲酯盐酸盐 | 6197-39-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 中文名称: 1,2,5,6-四氢吡啶-3-甲酸甲酯盐酸盐
• 英文名称: methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride
• 英文别名: Norarecoline hydrochloride；1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester hydrochloride；hydron;methyl 1,2,3,6-tetrahydropyridine-5-carboxylate;chloride
• CAS: 6197-39-3
• 化学式: C₇H₁₁NO₂*ClH
• 分子量: 177.631
• InChiKey: ZWALOEQHJRUTKM-UHFFFAOYSA-N

物化性质

• 熔点：
  121-122 °C
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 储存条件：
  2-8℃

制备方法与用途

化学性质：白色结晶粉末状物质，能溶解于甲醇、乙醇及DMSO等有机溶剂，源于槟榔。

用途：去甲槟榔碱具备抗癌和抗炎的功效。

反应信息

• 作为反应物：
  描述：

  1,2,5,6-四氢吡啶-3-甲酸甲酯盐酸盐 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.05h， 生成 3,6-二氢-1,3(2H)-吡啶二甲酸 1-叔丁酯 3-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
• 作为产物：
  描述：

  氢溴酸槟榔碱 在 1-氯乙基氯甲酸酯 、 sodium carbonate 、 1,2-二氯乙烷 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.25h， 生成 1,2,5,6-四氢吡啶-3-甲酸甲酯盐酸盐
  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
• 作为试剂：
  描述：

  氢溴酸槟榔碱 、 potassium carbonate 、 氯化钠 、 1-氯乙基氯甲酸酯 在 乙醚 、 Sodium sulfate-III 、 colourless oil 、 盐酸 、 甲醇 、 1,2,5,6-四氢吡啶-3-甲酸甲酯盐酸盐 作用下， 以 水 、 甲苯 为溶剂， 反应 18.0h， 生成 1,2,5,6-四氢吡啶-3-羧酸甲酯
  参考文献：
  名称：

  1H-Indole-Pyridinecarboxamide and 1H-Indole-Piperidinecarboxamide Compounds

  摘要：

  化学式为（I）的化合物：其中：A代表二价基团：其中：Z代表氧原子或硫原子，R6代表氢原子，烷基，烯基，芳基烷基或多卤代烷基或取代的，线性或支链烷基链，代表单键或双键，R1、R2、R3和R4代表氢或卤素原子，烷基，烷氧基，羟基，氰基，硝基，多卤代烷基或可选取代的氨基团，或被一个或多个基团取代的线性或支链烷基链，R5代表氢原子或烷基，氨基烷基或羟基烷基，X和Y代表氢原子或烷基，Ra、Rb、Rc和Rd代表氢或卤素原子，烷基，羟基，烷氧基，氰基，硝基，多卤代烷基，可选取代的氨基团，或取代的，线性或支链烷基链，Re代表氢原子或烷基，芳基烷基或烯基或取代的，线性或支链烷基链，它们的对映体，顺反异构体和N-氧化物，以及与药用可接受的酸或碱形成的加成盐。

  公开号：

  US20090258883A1

文献信息

• A General, Selective, High-Yield N-Demethylation Procedure for Tertiary Amines by Solid Reagents in a Convenient Column Chromatography-like Setup
  作者：Thomas Rosenau、Andreas Hofinger、Antje Potthast、Paul Kosma

  DOI：10.1021/ol036319g

  日期：2004.2.1

  [reaction: see text] A traditional preparative chromatographic column can be used to achieve quantitative N-demethylation of tertiary N-methylamines and alkaloids. The filling is the crucial part and is loaded with different solid reagents in three reaction zones. The parent compound is charged on the column, and the neat N-demethylated secondary amine leaves the column some minutes later.

  [反应：请参见文本]传统的制备型色谱柱可用于实现叔N-甲基胺和生物碱的定量N-去甲基化。填充物是至关重要的部分，在三个反应区中装有不同的固体试剂。将母体化合物装到色谱柱上，几分钟后，纯净的N-脱甲基仲胺离开色谱柱。
• Beta-sulfonamide hydroxamic acid inhibitors of tace/matrix metalloproteinase
  申请人：Levin I. Jeremy

  公开号：US20060211730A1

  公开（公告）日：2006-09-21

  This invention provides compounds of Formula I, having the structure: that are useful in treating diseases or disorders mediated by TNF-α, such as arthritis (rheumatoid arthritis (RA), juvenile RA, psoriatic arthritis, osteoarthritis etc), tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection, ankylosing spondylitis, psoriasis, sepsis, multiple sclerosis, Crohn's disease, degenerative cartilage loss, asthma, idiopathic pulmonary fibrosis, vasculitis, systemic lupus erythematosus, irritable bowel syndrome, acute coronary syndrome, hepatitis C, cachexia, COPD, stroke or type 2 diabetes, and for alleviation of symptoms thereof. The invention further provides methods for use of the compounds.

  这项发明提供了具有结构的Formula I的化合物，这些化合物在治疗由TNF-α介导的疾病或紊乱方面非常有用，如关节炎（类风湿关节炎（RA），幼年RA，银屑病性关节炎，骨关节炎等），肿瘤转移，组织溃疡，异常伤口愈合，牙周病，骨病，糖尿病（胰岛素抵抗）和HIV感染，强直性脊柱炎，银屑病，败血症，多发性硬化，克罗恩病，退行性软骨丢失，哮喘，特发性肺纤维化，血管炎，系统性红斑狼疮，肠易激综合征，急性冠状动脉综合征，丙型肝炎，虚弱，慢性阻塞性肺病，中风或2型糖尿病的缓解症状。该发明还提供了使用这些化合物的方法。
• [EN] SPIRO CYCLOPENTANE COMPOUNDS USEFUL AS ANTAGONISTS OF THE H1-RECEPTOR<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXO GROUP LTD

  公开号：WO2009016084A1

  公开（公告）日：2009-02-05

  This invention relates to novel spiro cyclopentane derivatives of formula (I) or a pharmaceutically acceptable salt thereof, for treating diseases and conditions of the central nervous system (CNS), in particular sleep disorders.

  该发明涉及公式（I）的新颖螺环戊烷衍生物或其药用盐，用于治疗中枢神经系统（CNS）的疾病和病症，特别是睡眠障碍。
• Inhibition of GABA uptake by N-substituted azaheterocyclic carboxylic
  申请人：Smithkline Beckman Corporation

  公开号：US04383999A1

  公开（公告）日：1983-05-17

  N-Substituted azaheterocyclic carboxylic acids and their esters, useful as inhibitors of GABA uptake, are prepared by reacting an appropriate N-alkylating derivative with an ester of an N-unsubstituted azaheterocyclic carboxylic acid followed by hydrolysis of the ester.

  N-取代的氮杂杂环羧酸及其酯，可用作GABA摄取抑制剂，通过将适当的N-烷基化衍生物与N-未取代的氮杂杂环羧酸酯反应，然后水解酯来制备。
• Carboxylic acid derivatives of N-substituted
  申请人：Imperial Chemical Industries Limited

  公开号：US04238488A1

  公开（公告）日：1980-12-09

  The invention concerns novel 1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid derivatives of the formula: ##STR1## wherein R.sup.1 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.

  该发明涉及一种新的1-苄基-1,2,5,6-四氢吡啶-3-羧酸衍生物，其化学式为：##STR1## 其中R.sup.1是羟基、氨基、(1-4C)烷基氨基、二[(1-4C)烷基]氨基、苄氧，可选择由卤素取代，或(1-6C)烷氧，可选择由(1-4C)烷氧取代、吗啉或二[(1-4C)烷基]氨基;苯环A带有一个或两个取代基，所选取代基为卤素、(1-4C)烷基、氰基、羧酰胺基、三氟甲基和羟基;以及其药学上可接受的盐；以及其药物组合物；以及其制造类似物的过程。该式I化合物是血小板聚集抑制剂，可能应用于治疗或预防血栓或闭塞性血管疾病。该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。