naphthalene-2,6-dicarboxylic acid monoethyl ester | 959282-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalene-2,6-dicarboxylic acid monoethyl ester
• 英文别名: 6-(Ethoxycarbonyl)-2-naphthoic acid；6-ethoxycarbonylnaphthalene-2-carboxylic acid
• CAS: 959282-81-6
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: QLHYQXZUBDTQCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  naphthalene-2,6-dicarboxylic acid monoethyl ester 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of N-(2-Oxo-3-oxetanyl)amides as N-Acylethanolamine-hydrolyzing Acid Amidase Inhibitors

  摘要：

  The fatty acid ethanolamides (FAEs) are a family of bioactive lipid mediators that include the endogenous agonist of peroxisome proliferator-activated receptor-alpha, palmitoylethanolamide (PEA). FAEs are hydrolyzed intracellularly by either fatty acid amide hydrolase or N-acylethanolamine-hydrolyzing acid amidase (NAAA). Selective inhibition of NAAA by (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide [(S)-OOPP, 7a] prevents PEA degradation in mouse leukocytes and attenuates responses to proinflammatory stimuli. Starting from the structure of 7a, a series of beta-lactones was prepared and tested on recombinant rat NAAA to explore structure-activity relationships (SARs) for this class of inhibitors and improve their in vitro potency. Following the hypothesis that these compounds inhibit NAAA by acylation of the catalytic cysteine, we identified several requirements for recognition at the active site and obtained new potent inhibitors. In particular, (S)-N-(2-oxo-3-oxetanyl)biphenyl-4-carboxamide (7h) was more potent than 7a at inhibiting recombinant rat NAAA activity (7a, IC(50) = 420 nM; 7h, IC(50) = 115 nM) in vitro and at reducing carrageenan-induced leukocyte infiltration in vivo.

  DOI：

  10.1021/jm100582w
• 作为产物：
  描述：

  2,6-萘二羧酸二乙酯 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以52%的产率得到naphthalene-2,6-dicarboxylic acid monoethyl ester
  参考文献：
  名称：

  Self-assembly of porphyrin–azulene–porphyrin and porphyrin–azulene conjugates

  摘要：

  本文报告了新型卟啉-氮烯-卟啉和卟啉-氮烯共轭物的合成和自组装行为。卟啉-氮烯-卟啉共轭物能在多种有机溶剂中凝胶化，而卟啉-氮烯共轭物则能在氯仿-甲醇二元混合物中形成囊泡。扫描电镜和原子力显微镜对有机凝胶和囊泡的结构进行了表征。此外，还制备了两种卟啉-萘-卟啉和卟啉-萘共轭物。将它们的性质与薁类似物的性质进行比较后发现，薁单元的分子间偶极和偶极相互作用在促进卟啉-薁-卟啉和卟啉-薁共轭物的自组装方面发挥了重要作用。

  DOI：

  10.1039/b904009a

文献信息

• A polyester composition and film
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP0755975B1

  公开（公告）日：2002-03-20
• Synthesis and Structure−Activity Relationships of <i>N</i>-(2-Oxo-3-oxetanyl)amides as <i>N</i>-Acylethanolamine-hydrolyzing Acid Amidase Inhibitors
  作者：Carlos Solorzano、Francesca Antonietti、Andrea Duranti、Andrea Tontini、Silvia Rivara、Alessio Lodola、Federica Vacondio、Giorgio Tarzia、Daniele Piomelli、Marco Mor

  DOI：10.1021/jm100582w

  日期：2010.8.12

  The fatty acid ethanolamides (FAEs) are a family of bioactive lipid mediators that include the endogenous agonist of peroxisome proliferator-activated receptor-alpha, palmitoylethanolamide (PEA). FAEs are hydrolyzed intracellularly by either fatty acid amide hydrolase or N-acylethanolamine-hydrolyzing acid amidase (NAAA). Selective inhibition of NAAA by (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide [(S)-OOPP, 7a] prevents PEA degradation in mouse leukocytes and attenuates responses to proinflammatory stimuli. Starting from the structure of 7a, a series of beta-lactones was prepared and tested on recombinant rat NAAA to explore structure-activity relationships (SARs) for this class of inhibitors and improve their in vitro potency. Following the hypothesis that these compounds inhibit NAAA by acylation of the catalytic cysteine, we identified several requirements for recognition at the active site and obtained new potent inhibitors. In particular, (S)-N-(2-oxo-3-oxetanyl)biphenyl-4-carboxamide (7h) was more potent than 7a at inhibiting recombinant rat NAAA activity (7a, IC(50) = 420 nM; 7h, IC(50) = 115 nM) in vitro and at reducing carrageenan-induced leukocyte infiltration in vivo.
• Self-assembly of porphyrin–azulene–porphyrin and porphyrin–azulene conjugates
  作者：Ze-Yun Xiao、Xin Zhao、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1039/b904009a

  日期：——

  In this paper we report the synthesis and self-assembling behavior of new porphyrin-azulene-porphyrin and porphyrin-azulene conjugates. The porphyrin-azulene-porphyrin conjugate gelates a number of organic solvents, while the porphyrin-azulene conjugates form vesicles in a chloroform–methanol binary mixture. The structures of the organogels and vesicles have been characterized by SEM and AFM. Two porphyrin-naphthalene-porphyrin and porphyrin-naphthalene conjugates were also prepared. A comparison of their properties with those of the azulene analogues reveals that the intermolecular dipole–dipole interaction of the azulene units plays an important role in promoting the self-assembly of the porphyrin-azulene-porphyrin and porphyrin-azulene conjugates.

  本文报告了新型卟啉-氮烯-卟啉和卟啉-氮烯共轭物的合成和自组装行为。卟啉-氮烯-卟啉共轭物能在多种有机溶剂中凝胶化，而卟啉-氮烯共轭物则能在氯仿-甲醇二元混合物中形成囊泡。扫描电镜和原子力显微镜对有机凝胶和囊泡的结构进行了表征。此外，还制备了两种卟啉-萘-卟啉和卟啉-萘共轭物。将它们的性质与薁类似物的性质进行比较后发现，薁单元的分子间偶极和偶极相互作用在促进卟啉-薁-卟啉和卟啉-薁共轭物的自组装方面发挥了重要作用。