4-formylnaphthalene-1-yloxyacetic acid methyl ester | 219684-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-formylnaphthalene-1-yloxyacetic acid methyl ester
• 英文别名: Methyl (4-formylnaphthalen-1-yloxy)acetate；methyl 2-(4-formylnaphthalen-1-yl)oxyacetate
• CAS: 219684-84-1
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: GQFUTCFWIUSKGY-UHFFFAOYSA-N

物化性质

• 沸点：
  416.4±20.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-formylnaphthalene-1-yloxyacetic acid methyl ester 在 sodium hydroxide 、 溶剂黄146 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 48.08h， 生成 3-Chloro-4-hydroxybenzoic Acid {4-[2-(1,2,3,4-Tetrahydroisoquinolin-2-yl)-2-oxoethoxy]naphth-1-ylmethylene}hydrazide
  参考文献：
  名称：

  Optimization of Alkylidene Hydrazide Based Human Glucagon Receptor Antagonists. Discovery of the Highly Potent and Orally Available 3-Cyano-4-hydroxybenzoic Acid [1-(2,3,5,6-Tetramethylbenzyl)-1H-indol-4-ylmethylene]hydrazide

  摘要：

  Highly potent human glucagon receptor (hGluR) antagonists have been prepared employing both medicinal chemistry and targeted libraries based on modification of the core (proximal) dimethoxyphenyl group, the benzyl ether linkage, as well as the (distal) benzylic aryl group of the lead 2, 3-eyano-4-hydroxybenzoic acid (3,5-dimethoxy-4-isopropylbenzyloxybenzylidene)hydrazide. Electron-rich proximal aryl moieties such as mono- and dimethoxy benzenes, naphthalenes, and indoles were found to be active. The SAR was found to be quite insensitive regarding the linkage to the distal aryl group, since long and short as well as polar and apolar linkers gave highly potent compounds. The presence of a distal aryl group was not crucial for obtaining high binding affinity to the hGluR. In many cases, however, the affinity could be further optimized with substituted distal aryl groups. Representative compounds have been tested for in vitro metabolism, and structure-metabolism relationships are described. These efforts lead to the discovery of 74, NNC 25-2504, 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6-tetramethylbenzyl)-1H-indol-4-ylmethylenelhydrazide, with low in vitro metabolic turnover. 74 was a highly potent noncompetitive antagonist of the human glucagon receptor (IC50 = 2.3 nM, K-B = 760 pM) and of the isolated rat receptor IC50 = 430 pM, K-B = 380 pM). Glucagon-stimulated glucose production from isolated primary rat hepatocytes was inhibited competitively by 74 (K-i = 14 nM). This compound was orally available in dogs (F-po = 15%) and was active in a glucagon-challenged rat model of hyperglucagonemia and hyperglycemia.

  DOI：

  10.1021/jm0208572
• 作为产物：
  描述：

  4-羟基-1-萘甲醛 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以92%的产率得到4-formylnaphthalene-1-yloxyacetic acid methyl ester
  参考文献：
  名称：

  构象受限的二吡咯亚甲基二氟化硼（BODIPY）染料：用于细胞成像的高荧光，彩色探针。

  摘要：

  通过在BODIPY核的内消旋位置引入萘基，已经制备了新型的荧光，构象受限的二吡咯亚甲基二氟化硼（BODIPY）染料。与具有内部旋转的中位苯基的染料相比，这些BODIPY染料具有更高的荧光量子产率。这种构象受限的BODIPY染料的吸收和发射波长可通过与苯甲醛衍生物的缩合反应进行衍生化而容易地调节到近红外范围。还研究了这些BODIPY染料的双光子吸收特性，结果表明，与含有苯基的类似染料相比，它们显示出增强的双光子激发荧光。

  DOI：

  10.1002/chem.200800309

文献信息

• [EN] GLUCAGON ANTAGONISTS/INVERSE AGONISTS<br/>[FR] ANTAGONISTES/AGONISTES INVERSES DU GLUCAGON
  申请人：NOVO NORDISK AS

  公开号：WO1999001423A1

  公开（公告）日：1999-01-14

  Non-peptide compounds comprising a central hydrazide motif and methods for the synthesis thereof. The compounds act to antagonize the action of the glucagon peptide hormone.

  非肽化合物包含一个中心肼基结构，并且其合成方法。这些化合物作用是拮抗胰高血糖素肽激素的作用。
• SUBSTITUTED PIPERAZINES, (1,4) DIAZEPINES, AND 2,5-DIAZABICYCLO (2.2.1) HEPTANES AS HISTAMINE H1 AND/OR H3 ANTAGONISTS OR HISTAMINE H3 REVERSE ANTAGONISTS
  申请人：Ancliff Rachael

  公开号：US20100075953A1

  公开（公告）日：2010-03-25

  The present invention relates to novel piperazine and azepine derivatives having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of neurodegenerative disorders including Alzheimer's disease.

  本发明涉及具有药理活性的新型哌嗪和氮杂七环衍生物，其制备过程，包含它们的组合物以及它们在治疗神经退行性疾病，包括阿尔茨海默病中的应用。
• GLUCAGON ANTAGONISTS/INVERSE AGONISTS
  申请人：NOVO NORDISK A/S

  公开号：EP0994848A1

  公开（公告）日：2000-04-26
• US6613942B1
  申请人：——

  公开号：US6613942B1

  公开（公告）日：2003-09-02