N-(2-hydroxyethyl)-2-(6-methoxynaphthalen-2-yl)propanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-hydroxyethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
• 英文别名: (2S)-N-(2-hydroxyethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: BPPSCWBKOSXGQD-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-2-(6-methoxynaphthalen-2-yl)propanamide 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 3.0h， 生成 N-(2-hydroxyethyl)-2-(6-methoxynaphthalen-2-yl)propan-1-ammonium chloride
  参考文献：
  名称：

  NSAIDs do not require the presence of a carboxylic acid to exert their anti-inflammatory effect – why do we keep using it?

  摘要：

  The carboxylic acid group (-COOH) present in classical NSAIDs is partly responsible for the gastric toxicity associated with the administration of these drugs. This concept has been extensively proven using NSAID prodrugs. However, the screening of NSAIDs with no carboxylic acid at all has been neglected. The goal of this work was to determine if new NSAID derivatives devoid of acidic moieties would retain the anti-inflammatory activity of the parent compound, without causing gastric toxicity. To test this concept, we replaced the carboxylic acid group in ibuprofen, flurbiprofen, and naproxen with three ammonium moieties. We tested the resulting water-soluble NSAID derivatives for anti-inflammatory and ulcerogenic activity in vitro and in vivo. In this regard, we observed that all non-acidic NSAIDs exerted a potent antiinflammatory activity, suggesting that the acid group in commercial 2-phenylpropionic acid NSAIDs not be an essential requirement for anti-inflammatory activity. These data provide complementary evidence supporting the discontinuation of ulcerogenic acidic NSAIDs.

  DOI：

  10.3109/14756366.2015.1088840
• 作为产物：
  描述：

  萘普生 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-(2-hydroxyethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
  参考文献：
  名称：

  NSAIDs do not require the presence of a carboxylic acid to exert their anti-inflammatory effect – why do we keep using it?

  摘要：

  The carboxylic acid group (-COOH) present in classical NSAIDs is partly responsible for the gastric toxicity associated with the administration of these drugs. This concept has been extensively proven using NSAID prodrugs. However, the screening of NSAIDs with no carboxylic acid at all has been neglected. The goal of this work was to determine if new NSAID derivatives devoid of acidic moieties would retain the anti-inflammatory activity of the parent compound, without causing gastric toxicity. To test this concept, we replaced the carboxylic acid group in ibuprofen, flurbiprofen, and naproxen with three ammonium moieties. We tested the resulting water-soluble NSAID derivatives for anti-inflammatory and ulcerogenic activity in vitro and in vivo. In this regard, we observed that all non-acidic NSAIDs exerted a potent antiinflammatory activity, suggesting that the acid group in commercial 2-phenylpropionic acid NSAIDs not be an essential requirement for anti-inflammatory activity. These data provide complementary evidence supporting the discontinuation of ulcerogenic acidic NSAIDs.

  DOI：

  10.3109/14756366.2015.1088840

文献信息

• NSAIDs do not require the presence of a carboxylic acid to exert their anti-inflammatory effect – why do we keep using it?
  作者：Nasir Ullah、Zhangjian Huang、Forough Sanaee、Alexandra Rodriguez-Dimitrescu、Fahad Aldawsari、Fakhreddin Jamali、Atul Bhardwaj、Nazar Ul Islam、Carlos A. Velázquez-Martínez

  DOI：10.3109/14756366.2015.1088840

  日期：2016.11.1

  The carboxylic acid group (-COOH) present in classical NSAIDs is partly responsible for the gastric toxicity associated with the administration of these drugs. This concept has been extensively proven using NSAID prodrugs. However, the screening of NSAIDs with no carboxylic acid at all has been neglected. The goal of this work was to determine if new NSAID derivatives devoid of acidic moieties would retain the anti-inflammatory activity of the parent compound, without causing gastric toxicity. To test this concept, we replaced the carboxylic acid group in ibuprofen, flurbiprofen, and naproxen with three ammonium moieties. We tested the resulting water-soluble NSAID derivatives for anti-inflammatory and ulcerogenic activity in vitro and in vivo. In this regard, we observed that all non-acidic NSAIDs exerted a potent antiinflammatory activity, suggesting that the acid group in commercial 2-phenylpropionic acid NSAIDs not be an essential requirement for anti-inflammatory activity. These data provide complementary evidence supporting the discontinuation of ulcerogenic acidic NSAIDs.