2-(5-Chloro-2-isocyanatophenoxy)naphthalene | 160693-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-Chloro-2-isocyanatophenoxy)naphthalene
• CAS: 160693-22-1
• 化学式: C₁₇H₁₀ClNO₂
• 分子量: 295.725
• InChiKey: PWNYLGFZTVKUQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,5-二氧杂螺[5.5]十一烷-2,4-二酮 、 2-(5-Chloro-2-isocyanatophenoxy)naphthalene 在 三乙胺 作用下， 以48%的产率得到N-(4-chloro-2-naphthalen-2-yloxyphenyl)-2-hydroxy-4-oxo-1,5-dioxaspiro[5.5]undec-2-ene-3-carboxamide
  参考文献：
  名称：

  A new class of inhibitors of secretory phospholipase A2: enolized 1,3-dioxane-4,6-dione-5-carboxamides

  摘要：

  Enolized 1,3-dioxane-4,6-dione-5-carboxamides a were identified as a new class of inhibitors of secretory phospholipase A(2) from human polymorphonuclear leucocytes (h-PMN PLA(2)). Among the more than 30 compounds synthesized, the most potent inhibitors (IC50 0.6-10 mu M) were found in the series of 2,4-disubstituted phenyl analogues of a. Compound 1a was selected for evaluation of its biological profile. This substance potently inhibited secretory PLA(2)s from several sources other than human PMNs, with a clear preference for group II over group I PLA(2), whereas human cytosolic PLA(2) and phospholipase C were not significantly affected. Inhibition of h-PMN PLA(2) was calcium-dependent. In intact mammalian cells stimulated in vitro, the release of arachidonic acid and the generation of prostaglandins and leukotrienes were inhibited at concentrations compatible with inhibition of PLA(2) as an underlying mechanism. In animal models in vivo (carragheenan oedema, adjuvant arthritis, pertussis pleurisy) 1a showed antiinflammatory activity, although the effect was rather weak compared with standard reference compounds.

  DOI：

  10.1016/0223-5234(94)90026-4
• 作为产物：
  描述：

  三光气 、 4-chloro-2-[2]naphthyloxy-aniline 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 2-(5-Chloro-2-isocyanatophenoxy)naphthalene
  参考文献：
  名称：

  A new class of inhibitors of secretory phospholipase A2: enolized 1,3-dioxane-4,6-dione-5-carboxamides

  摘要：

  Enolized 1,3-dioxane-4,6-dione-5-carboxamides a were identified as a new class of inhibitors of secretory phospholipase A(2) from human polymorphonuclear leucocytes (h-PMN PLA(2)). Among the more than 30 compounds synthesized, the most potent inhibitors (IC50 0.6-10 mu M) were found in the series of 2,4-disubstituted phenyl analogues of a. Compound 1a was selected for evaluation of its biological profile. This substance potently inhibited secretory PLA(2)s from several sources other than human PMNs, with a clear preference for group II over group I PLA(2), whereas human cytosolic PLA(2) and phospholipase C were not significantly affected. Inhibition of h-PMN PLA(2) was calcium-dependent. In intact mammalian cells stimulated in vitro, the release of arachidonic acid and the generation of prostaglandins and leukotrienes were inhibited at concentrations compatible with inhibition of PLA(2) as an underlying mechanism. In animal models in vivo (carragheenan oedema, adjuvant arthritis, pertussis pleurisy) 1a showed antiinflammatory activity, although the effect was rather weak compared with standard reference compounds.

  DOI：

  10.1016/0223-5234(94)90026-4