3-(2-naphthalenylmethoxy)nitrobenzene | 79807-83-3

• 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: 3-(2-naphthalenylmethoxy)nitrobenzene
• 英文别名: 3-(2-naphthylmethoxy)-1-nitrobenzene；2-[(3-Nitrophenoxy)methyl]naphthalene
• CAS: 79807-83-3
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: ALQDCCUNPSFLQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-naphthalenylmethoxy)nitrobenzene 在 palladium on activated charcoal 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-{[3-(2-naphthalenylmethoxy)phenyl]hydroxyamino}-4-oxobutanoic acid, methyl ester
  参考文献：
  名称：

  [[[（萘甲氧基甲氧基）-和[[（喹啉基甲氧基）苯基]氨基]氧代链烷酸酯的合成。一系列新的白三烯D4拮抗剂和5-脂氧合酶抑制剂。

  摘要：

  已经制备了一系列新型的[[（（萘基甲氧基）-和[[（喹啉基甲氧基）苯基]氨基]氧代链烷酸酯。在体外测试了这些化合物作为大鼠多形核白细胞（PMN）5-脂氧合酶（LO）的抑制剂以及卵白蛋白（OA）和白三烯D4（LTD4）诱导的豚鼠（GP）支气管痉挛的抑制剂。GP中许多萘化合物是5-LO的有效抑制剂，而一些喹啉基化合物是LTD4介导的支气管痉挛的有效抑制剂。最有效的萘化合物4-[[[3-（2-萘甲氧基甲氧基）苯基]羟基氨基] -4-氧代丁酸甲酯（6v）在5-LO分析中的IC50为0.6 microM。体内最有效的化合物4-[[[3-（2-喹啉基甲氧基）苯基]羟基氨基] -4-氧代丁酸甲酯（6e）的ED50为3.3 mg / kg，为27。分别针对LTD4-和OA引起的支气管痉挛分别为4 mg / kg（十二指肠内）。当作为LTD4诱导的分离GP气管螺旋带收缩的拮抗剂进行测试时，显示6e是竞争性抑制剂，pKB值为5

  DOI：

  10.1021/jm00158a019
• 作为产物：
  描述：

  间硝基苯酚 、 2-溴甲基萘 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到3-(2-naphthalenylmethoxy)nitrobenzene
  参考文献：
  名称：

  4-Hydroxyquinoline-3-carboxylic acids as inhibitors of cell respiration. 2. Quantitative structure-activity relationship of dehydrogenase enzyme and Ehrlich ascites tumor cell inhibitions

  摘要：

  Studies on dehydrogenase enzyme inhibition have been extended with the design, synthesis, and correlation analysis of 7-[(substituted-benzyl)oxy]-, 7-[(substituted-phenethyl)oxy]-, and 7([substituted-phenoxy)ethoxy]-4-hydroxyquinoline-3-carboxylic acids. Sixteen new congeners and the fifteen molecules previously synthesized have been tested against cytoplasmic malate dehydrogenase and lactate dehydrogenase, as well as against mitochondrial malate dehydrogenase. The lipophilic congeners show a clear specificity for inhibition of the mitochondrial enzyme. Correlation analysis of the data on the three enzymes allows a comparison of the binding sites in quantitative terms, while examination of the data on inhibition of ascites tumor cell respiration affords an indication of membrane transport. A newly developed high-pressure liquid chromatography based retention index is compared to the octanol-water pi constant as a model for hydrophobic interactions.

  DOI：

  10.1021/jm00343a011

文献信息

• N-[(Arylmethoxy)phenyl] and N-[(arylmethoxy)naphthyl] sulfonamides: potent orally active leukotriene d4 antagonists of novel structure
  作者：John H. Musser、Anthony F. Kreft、Reinhold H. W. Bender、Dennis M. Kubrak、Richard P. Carlson、Joseph Chang、James M. Hand

  DOI：10.1021/jm00126a006

  日期：1989.6

  Two series of compounds, N-[(arylmethoxy)phenyl] sulfonamides and N-[(arylmethoxy)naphthyl] sulfonamides, were prepared as leukotriene D4 (LTD4) antagonists. In the phenyl series, N-[3-(2-quinolinylmethoxy)phenyl]-trifluoromethanesulfonamide (Wy-48,252, 16) was the most potent inhibitor of LTD4-induced bronchoconstriction in the guinea pig. With an intragastric ID50 of 0.1 mg/kg (2-h pretreatment), 16 was 300 times more potent than LY-171,883. Compound 16 also intragastrically inhibited ovalbumin-induced bronchoconstriction in the guinea pig with an ID50 of 0.6 mg/kg. In vitro against LTD4-induced contraction of isolated guinea pig trachea pretreated with indomethacin and L-cysteine, 16 produced a pKB value of 7.7. In the rat PMN assay 16 inhibited both 5-lipoxygenase and cyclooxygenase (IC50's = 4.6 and 3.3 microM). In the naphthyl series, N-[7-(2-quinolinylmethoxy)-2-naphthyl]trifluoromethanesulfonamide (Wy-48,090, 47) in addition to potent LTD4 antagonist activity (on isolated guinea pig trachea 47 had a pKB value of 7.04) also had antiinflammatory activity (63% inhibition at 50 mg/kg in the rat carrageenan paw edema assay and 34% inhibition of TPA-induced inflammation at 1 mg/ear in the mouse ear edema model). Perhaps the antiinflammatory activity of 47 was due to its additional activity of inhibiting both 5-lipoxygenase and cyclooxygenase enzymes (IC50's = 0.23 and 11.9 microM, respectively, in rat PMN).
• MUSSER J. H.; KUBRAK D. M.; CHANG J.; LEWIS A. J., J. MED. CHEM., 29,(1986) N 8, 1429-1435
  作者：MUSSER J. H.、 KUBRAK D. M.、 CHANG J.、 LEWIS A. J.

  DOI：——

  日期：——