5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-ethyl ester 3-methyl ester | 74719-24-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-ethyl ester 3-methyl ester
• 英文别名: 1-ethyl 3-methyl-5,6-dihydropyridine-1,3(2H)-dicarboxylate；1-O-ethyl 5-O-methyl 3,6-dihydro-2H-pyridine-1,5-dicarboxylate
• CAS: 74719-24-7
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: OZCUQZUMOUQYNG-UHFFFAOYSA-N

物化性质

• 沸点：
  120-130 °C(Press: 1.1 Torr)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-ethyl ester 3-methyl ester 在 吡啶 、 sodium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 15.17h， 生成 5-Acetyl-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  5-(Alk-1-enyl)-1,2,3,6-tetrahydropyridines as congeners of streptazolin

  摘要：

  描述了与抗生素和抗真菌活性独特天然化合物链霉唑（streptazolin）结构相关的1,3-二烯的合成。模仿两个建议的药效团单元导致了具有增强化学稳定性的化合物，但抗生素活性并没有令人满意的提升。

  DOI：

  10.1039/a607309c
• 作为产物：
  描述：

  氢溴酸槟榔碱 在 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 3.75h， 生成 5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-ethyl ester 3-methyl ester
  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

• Heterotricyclic Himbacine Analogs as Potent, Orally Active Thrombin Receptor (Protease Activated Receptor-1) Antagonists
  作者：Mariappan V. Chelliah、Samuel Chackalamannil、Yan Xia、Keith Eagen、Martin C. Clasby、Xiaobang Gao、William Greenlee、Ho-Sam Ahn、Jacqueline Agans-Fantuzzi、George Boykow、Yunsheng Hsieh、Matthew Bryant、Jairam Palamanda、Tze-Ming Chan、David Hesk、Madhu Chintala

  DOI：10.1021/jm070704k

  日期：2007.10.1

  Pursuing our earlier efforts in the himbacine-based thrombin receptor antagonist area, we have synthesized a series of compounds that incorporate heteroatoms in the C-ring of the tricyclic motif. This effort has resulted in the identification of several potent heterocyclic analogs with excellent affinity for the thrombin receptor. Several of these compounds demonstrated robust inhibition of platelet

  遵循我们在基于组氨酸的凝血酶受体拮抗剂领域的早期努力，我们合成了一系列在三环基序的C环中掺入杂原子的化合物。这项工作已导致鉴定出几种对凝血酶受体具有优异亲和力的有效杂环类似物。这些化合物中的几种在口服给药后在食蟹猴的离体模型中显示出对血小板聚集的强烈抑制。介绍了28b（本系列的基准化合物）的详细资料，Ki为4.3 nM。
• Thrombin receptor antagonists
  申请人：Schering Corporation

  公开号：US20030203927A1

  公开（公告）日：2003-10-30

  Heterocyclic-substituted tricyclics of the formula 1 or a pharmaceutically acceptable salts thereof, wherein: n 1 and n 2 are independently 0-2; Het is an optionally substituted mono-, bi- or tricyclic heteroaromatic group; B is alkyl or optionally substituted alkenyl; R 22 is —COR 23 or a carboxy, sulfinyl, sulfonyl, sulfonamide or amino acid derivative; R 23 is haloalkyl; alkenyl; haloalkenyl; alkynyl; optionally substituted cycloalkyl; cycloalkyl-alkyl; aryl; arylalkyl; heteroaryl; heterocycloalkyl; or —COOH and/or —SO 3 H substituted alkyl; R 1 , R 2 , R 3 , R 9 , R 10 and R 11 are as defined in the specification; are disclosed, as well as pharmaceutical compositions containing them and a method of treating diseases associated with thrombosis, atherosclerosis, restenosis, hypertension, angina pectoris, arrhythmia, heart failure, and cancer by administering said compounds.

  公式1中的杂环取代的三环化合物或其药学上可接受的盐，其中：n1和n2独立地为0-2；Het是可选择取代的单环、双环或三环杂芳基基团；B是烷基或可选择取代的烯基；R22是-COR23或羧基、亚磺酰基、磺酰基、磺酰胺或氨基酸衍生物；R23是卤代烷基；烯基；卤代烯基；炔基；可选择取代的环烷基；环烷基-烷基；芳基；芳基烷基；杂芳基；杂环烷基；或取代的-COOH和/或-SO3H的烷基；R1、R2、R3、R9、R10和R11如规范所定义；公开了含有它们的制药组合物以及通过给予所述化合物治疗与血栓形成、动脉粥样硬化、再狭窄、高血压、心绞痛、心律失常、心力衰竭和癌症相关的疾病的方法。
• [EN] HIMBACINE ANALOGUES AS THROMBIN RECEPTOR ANTAGONISTS<br/>[FR] ANALOGUES D'HIMBACINE TELS QUE DES ANTAGONISTES RECEPTEURS DE LATHROMBINE
  申请人：SCHERING CORP

  公开号：WO2003033501A1

  公开（公告）日：2003-04-24

  Heterocyclic-substituted tricyclics of the formula (I) or a pharmaceutically acceptable salts thereof, wherein: n1 and n2 are independently 0-2; Het is an optionally substituted mono-, bi- or tricyclic heteroaromatic group; B is alkyl or optionally substituted alkenyl; R22 is -COR23 or a carboxy, sulfinyl, sulfonyl, sulfonamide or amino acid derivative; R23 is haloalkyl; alkenyl; haloalkenyl; alkynyl; optionally substituted cycloalkyl; cycloalkyl-alkyl; aryl; arylalkyl; heteroaryl; heterocycloalkyl; or -COOH and/or -SO¿3?H substituted alkyl; R?1, R2, R3, R9, R10 and R11¿ are as defined in the specification; are disclosed, as well as pharmaceutical compositions containing them and a method of treating diseases associated with thrombosis, atherosclerosis, restenosis, hypertension, angina pectoris, arrhythmia, heart failure, and cancer by administering said compounds.

  公式（I）中的杂环取代三环化合物或其药学上可接受的盐，其中：n1和n2独立地为0-2；Het是一个可选取代的单环、双环或三环杂芳基团；B是烷基或可选取代的烯基；R22为-COR23或羧基、亚砜基、磺酰基、磺酰胺或氨基酸衍生物；R23为卤代烷基、烯基、卤代烯基、炔基、可选取代的环烷基、环烷基-烷基、芳基、芳基烷基、杂芳基、杂环烷基或-COOH和/或-SO3H取代的烷基；R1、R2、R3、R9、R10和R11如说明书中所定义；还公开了含有它们的药物组合物和通过给予这些化合物治疗与血栓形成、动脉粥样硬化、再狭窄、高血压、心绞痛、心律失常、心力衰竭和癌症相关的疾病的方法。
• CHRISTENSEN S. B.; KROGSGAARD-LARSEN P., J. LABELLED COMPOUNDS AND RADIOPHARM., 1980, 17, NO 2, 191-202
  作者：CHRISTENSEN S. B.、 KROGSGAARD-LARSEN P.

  DOI：——

  日期：——
• HIMBACINE ANALOGUES AS THROMBIN RECEPTOR ANTAGONISTS
  申请人：SCHERING CORPORATION

  公开号：EP1436298A1

  公开（公告）日：2004-07-14

表征谱图