ethyl 6-methyl-8-nitro-4-oxo-4H-chromene-2-carboxylate | 859843-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl 6-methyl-8-nitro-4-oxo-4H-chromene-2-carboxylate
• 英文别名: ethyl 8-nitro-6-methyl-4-oxo-4H-chromene-2-carboxylate；Ethyl 6-methyl-8-nitro-4-oxo-4H-1-benzopyran-2-carboxylate；ethyl 6-methyl-8-nitro-4-oxochromene-2-carboxylate
• CAS: 859843-61-1
• 化学式: C₁₃H₁₁NO₆
• 分子量: 277.233
• InChiKey: DIUVEXJPSYJVQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 6-methyl-8-nitro-4-oxo-4H-chromene-2-carboxylate 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， -10.0~60.0 ℃ 、1000.0 kPa 条件下， 反应 59.0h， 生成 ethyl 8-[(4-cyanobenzoyl)amino]-6-methyl-2-chromanecarboxylate
  参考文献：
  名称：

  Convenient Synthesis and Reactivity of Ethyl 8‐amino‐6‐methyl‐2,3‐dihydro‐4H‐1‐benzopyran‐2‐carboxylate

  摘要：

  We report and comprehensively describe the synthesis and reactivity of ethyl 8-amino-6-methyl-3,4-dihydro-2H-1-benzopyran-2-carboxylate. This peptidomimetic building block provides a constrained template that allows for the introduction of various functionalities in a specific spatial orientation.

  DOI：

  10.1081/scc-200057984
• 作为产物：
  描述：

  2-羟基-5-甲基苯乙酮 在 盐酸 、 硝酸 、 sodium ethanolate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 ethyl 6-methyl-8-nitro-4-oxo-4H-chromene-2-carboxylate
  参考文献：
  名称：

  Convenient Synthesis and Reactivity of Ethyl 8‐amino‐6‐methyl‐2,3‐dihydro‐4H‐1‐benzopyran‐2‐carboxylate

  摘要：

  We report and comprehensively describe the synthesis and reactivity of ethyl 8-amino-6-methyl-3,4-dihydro-2H-1-benzopyran-2-carboxylate. This peptidomimetic building block provides a constrained template that allows for the introduction of various functionalities in a specific spatial orientation.

  DOI：

  10.1081/scc-200057984

文献信息

• 6-Bromo-8-(4-[³H]methoxybenzamido)-4-oxo-4<i>H</i>-chromene-2-carboxylic Acid: A Powerful Tool for Studying Orphan G Protein-Coupled Receptor GPR35
  作者：Dominik Thimm、Mario Funke、Anne Meyer、Christa E. Müller

  DOI：10.1021/jm4009373

  日期：2013.9.12

  The potent and selective GPR35 agonist 6-bromo-8-(4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (12) was obtained in tritium-labeled form, designated [H-3]PSB-13253, with a specific activity of 36 Ci (1.33 TBq)/mmol. Radiolabeling was achieved by methylation of ethyl 6-bromo-8-(4-((tert-butyldimethylsilyl)oxy)benzamido)-4-oxo-4H-Chromene-2-carboxylate (19) with [H-3]methyl tosylate followed by ester hydrolysis. The radioligand was characterized by kinetic, saturation, and competition assays at membrane preparations of Chinese hamster ovary cells recombinantly expressing the human GPR35. [H-3]12 labeled the receptor with high affinity (K-D = 5.27 nM). Binding was saturable (B-max = 12.6 pmol/mg of protein) and reversible. Affinities of selected standard ligands and a library of amidochromen-4-one-2-carboxylates were determined. Binding data mostly correlated with potencies determined in beta-arrestin assays. On the basis of the test results, several new fluorine-substituted 6-bromo-8-benzamidochromen-4-one-2-carboxylic acids were obtained, which represent the most potent GPR35 agonists known to date. 6-Bromo-8-(2,6-difluoro-4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (83; K-i = 0.589 nM, EC50 = 5.54 nM) showed the highest affinity with a K-i value in the subnanomolar range.
• Convenient Synthesis and Reactivity of Ethyl 8‐amino‐6‐methyl‐2,3‐dihydro‐4<i>H</i>‐1‐benzopyran‐2‐carboxylate
  作者：Marko Anderluh、Gašper Marc、Marija Sollner Dolenc

  DOI：10.1081/scc-200057984

  日期：2005.6

  We report and comprehensively describe the synthesis and reactivity of ethyl 8-amino-6-methyl-3,4-dihydro-2H-1-benzopyran-2-carboxylate. This peptidomimetic building block provides a constrained template that allows for the introduction of various functionalities in a specific spatial orientation.