6-(叔丁基)-4-氧代-4H-吡喃-3-羧酸乙酯 | 134653-81-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 6-(叔丁基)-4-氧代-4H-吡喃-3-羧酸乙酯
• 英文名称: ethyl 6-tert-butyl-4-oxo-4H-pyran-3-carboxylate
• 英文别名: 3-carbethoxy-6-(1,1-dimethylethyl)-4-pyrone；6-tert-butyl-4-oxo-4H-pyran-3-carboxylic acid ethyl ester；Ethyl 6-(tert-butyl)-4-oxo-4H-pyran-3-carboxylate；ethyl 6-tert-butyl-4-oxopyran-3-carboxylate
• CAS: 134653-81-9
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: MCVPTHYFVGKZET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  6-(叔丁基)-4-氧代-4H-吡喃-3-羧酸乙酯 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 N3-(1-adamantyl)-6-tert-butyl-1-pentyl-4-oxo-1,4-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  4-Oxo-1,4-dihydropyridines as Selective CB₂ Cannabinoid Receptor Ligands: Structural Insights into the Design of a Novel Inverse Agonist Series

  摘要：

  Growing evidence shows that CB2 receptor is an attractive therapeutic target. Starting from a series of 4-oxo-1,4-dihydroquinoline-3-carboxamide as selective CB2 agonists, we describe here the medicinal chemistry approach leading to the development of CB2 receptor inverse agonists with a 4-oxo-1,4-dihydropyridine scaffold. The compounds reported here show high affinity and potency at the CB2, receptor while showing only modest affinity for the centrally expressed CB1 cannabinoid receptor. Further, we found that the functionality of this series is controlled by its C-6 substituent because agonists bear a methyl or a tert-butyl group and inverse agonists, a phenyl or 4-chlorophenyl group, respectively. Finally, in silico studies suggest that the C-6 substituent could modulate the conformation of W6.48 known to be critical in GPCR activation.

  DOI：

  10.1021/jm100286k
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 二甲基硫 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 6-(叔丁基)-4-氧代-4H-吡喃-3-羧酸乙酯
  参考文献：
  名称：

  4-Oxo-1,4-dihydropyridines as Selective CB₂ Cannabinoid Receptor Ligands Part 2: Discovery of New Agonists Endowed with Protective Effect Against Experimental Colitis

  摘要：

  Further on to our earlier work on the 4-oxo-1,4-dihydropyridine, we describe herein our strategy to get access to potent selective CB2 receptor agonists. Thus, we designed and synthesized 29 compounds, evaluated on both hCB(1) and hCB(2) cannabinoid receptors, and assessed 11 of them in the TNBS-induced colitis model in mice. Compound 48 was found to be the most efficient of our series, exhibiting an exquisite protection against experimental colitis, superior to the one observed after treatment with Pentasa.

  DOI：

  10.1021/jm3008568

文献信息

• [EN] CHIRAL CIS-IMIDAZOLINES<br/>[FR] CIS-IMIDAZOLINES CHIRALES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2009047161A1

  公开（公告）日：2009-04-16

  There are provided compounds of Formula (I), or the pharmaceutically acceptable salts thereof, wherein X, Y, Z, V1, V2, R1, R2, R3, R4 and R5 are as herein described, processes for obtaining said compounds and pharmaceutical preparations containing them. These compounds are useful as anticancer agents, in particular as agents in the treatment of solid tumors.

  提供了式（I）的化合物，或其药学上可接受的盐，其中X、Y、Z、V1、V2、R1、R2、R3、R4和R5如本文所述，获得该化合物的方法以及含有它们的药物制剂。这些化合物可用作抗癌剂，特别是作为固体肿瘤治疗中的药物。
• [EN] 1,4 DIHYDROPYRIDINE DERIVATIVES AND THEIR USES<br/>[FR] DÉRIVÉS DE LA 1,4-DIHYDROPYRIDINE ET LEURS UTILISATIONS
  申请人：UNIV LILLE II DROIT & SANTE

  公开号：WO2010133973A1

  公开（公告）日：2010-11-25

  The present invention relates to 1,4-dihydropyridine derivatives of the formula (I) and their uses in the treatment and/or prevention of diseases and disorders directly or indirectly associated with the modification (increase or decrease) of the activity of the cannabinoid receptor 2 (CB2).

  本发明涉及式(I)的1,4-二氢吡啶衍生物及其在治疗和/或预防与大麻素受体2（CB2）的活性修改（增加或减少）直接或间接相关的疾病和紊乱中的用途。
• CHIRAL CIS-IMIDAZOLINES
  申请人：Bartkovitz David Joseph

  公开号：US20090111789A1

  公开（公告）日：2009-04-30

  There are provided compounds of the formula or the pharmaceutically acceptable salts thereof, wherein X, Y, Z, V 1 , V 2 , R 1 , R 2 , R 3 , R 4 and R 5 are herein described. These compounds are useful as anticancer agents.

  提供以下公式或其药学上可接受的盐的化合物，其中X、Y、Z、V1、V2、R1、R2、R3、R4和R5在此描述。这些化合物可用作抗癌剂。
• 1,4-Dihydropyridine Derivatives and Their Uses
  申请人：Millet Regis

  公开号：US20120149735A1

  公开（公告）日：2012-06-14

  The present invention relates to 1,4-dihydropyridine derivatives of the formula (I) and their uses in the treatment and/or prevention of diseases and disorders directly or indirectly associated with the modification (increase or decrease) of the activity of the cannabinoid receptor 2 (CB2).

  本发明涉及式（I）的1,4-二氢吡啶衍生物及其在治疗和/或预防与大麻素受体2（CB2）的活性调节（增加或减少）直接或间接相关的疾病和障碍方面的用途。
• Chiral cis-imidazolines
  申请人：Bartkovitz David Joseph

  公开号：US08513239B2

  公开（公告）日：2013-08-20

  There are provided compounds of the formula or the pharmaceutically acceptable salts thereof, wherein X, Y, Z, V1, V2, R1, R2, R3, R4 and R5 are herein described. These compounds are useful as anticancer agents.

  提供了以下式子或其药学上可接受的盐，其中X、Y、Z、V1、V2、R1、R2、R3、R4和R5在此被描述。这些化合物可用作抗癌剂。