(S)-2-[2-(6-methoxynaphthyl-2-yl)propionoyloxy]ethanesulfonyl chloride | 1268343-94-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-[2-(6-methoxynaphthyl-2-yl)propionoyloxy]ethanesulfonyl chloride
• 英文别名: 2-chlorosulfonylethyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
• CAS: 1268343-94-7
• 化学式: C₁₆H₁₇ClO₅S
• 分子量: 356.827
• InChiKey: NQGOSACHCUAKHO-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-[2-(6-methoxynaphthyl-2-yl)propionoyloxy]ethanesulfonyl chloride 在 盐酸羟胺 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75.7%的产率得到(S)-(+)-2-[2-(6-methoxynaphthyl-2-yl)propionoyloxy]ethanesulfonylhydroxamic acid
  参考文献：
  名称：

  Ethanesulfohydroxamic Acid Ester Prodrugs of Nonsteroidal Anti-inflammatory Drugs (NSAIDs): Synthesis, Nitric oxide and Nitroxyl Release, Cyclooxygenase Inhibition, Anti-inflammatory, and Ulcerogenicity Index Studies

  摘要：

  The carboxylic acid group of the anti-inflammatory (AI) drugs indomethacin, (S)-naproxen and ibuprofen was covalently linked via a two-carbon ethyl spacer to a sulfohydroxamic acid moiety (CH2CH2SO2NHOH) to furnish a group of hybrid ester prodrugs that release nitric oxide (NO) and nitroxyl (HNO). Biological data acquired for this hitherto unknown class of ethanesulfohydroxamic acid ester prodrugs showed (i) all compounds exhibited superior NO, but similar HNO, release properties relative to arylsulfohydroxamic acids, (ii) the (S)-naproxen and ibuprofen prodrug esters are more potent AI agents than their parent NSAID, (iii) the indomethacin prodrug ester, in contrast to indomethacin which is highly ulcerogenic, showed no visible stomach lesions [ulcer index (UI) = 0 for a 80 mu mol/kg oral dose] while retaining potent AI activity, and iv) that the indomethacin prodrug ester, unlike indomethacin which is an ulcerogenic selective COX-1 inhibitor, is a selective COX-2 inhibitor (COX-2 selectivity index = 184) devoid of ulcerogenicity that is attributed to its high COX-2 SI and/or ability to release cytoprotective NO.

  DOI：

  10.1021/jm101403g
• 作为产物：
  描述：

  (S)-2-(6-甲氧基-2-萘基)丙酰氯 在 吡啶 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (S)-2-[2-(6-methoxynaphthyl-2-yl)propionoyloxy]ethanesulfonyl chloride
  参考文献：
  名称：

  Ethanesulfohydroxamic Acid Ester Prodrugs of Nonsteroidal Anti-inflammatory Drugs (NSAIDs): Synthesis, Nitric oxide and Nitroxyl Release, Cyclooxygenase Inhibition, Anti-inflammatory, and Ulcerogenicity Index Studies

  摘要：

  The carboxylic acid group of the anti-inflammatory (AI) drugs indomethacin, (S)-naproxen and ibuprofen was covalently linked via a two-carbon ethyl spacer to a sulfohydroxamic acid moiety (CH2CH2SO2NHOH) to furnish a group of hybrid ester prodrugs that release nitric oxide (NO) and nitroxyl (HNO). Biological data acquired for this hitherto unknown class of ethanesulfohydroxamic acid ester prodrugs showed (i) all compounds exhibited superior NO, but similar HNO, release properties relative to arylsulfohydroxamic acids, (ii) the (S)-naproxen and ibuprofen prodrug esters are more potent AI agents than their parent NSAID, (iii) the indomethacin prodrug ester, in contrast to indomethacin which is highly ulcerogenic, showed no visible stomach lesions [ulcer index (UI) = 0 for a 80 mu mol/kg oral dose] while retaining potent AI activity, and iv) that the indomethacin prodrug ester, unlike indomethacin which is an ulcerogenic selective COX-1 inhibitor, is a selective COX-2 inhibitor (COX-2 selectivity index = 184) devoid of ulcerogenicity that is attributed to its high COX-2 SI and/or ability to release cytoprotective NO.

  DOI：

  10.1021/jm101403g

文献信息

• Ethanesulfohydroxamic Acid Ester Prodrugs of Nonsteroidal Anti-inflammatory Drugs (NSAIDs): Synthesis, Nitric oxide and Nitroxyl Release, Cyclooxygenase Inhibition, Anti-inflammatory, and Ulcerogenicity Index Studies
  作者：Zhangjian Huang、Carlos A. Velázquez、Khaled R. A. Abdellatif、Morshed A. Chowdhury、Julie A. Reisz、Jenna F. DuMond、S. Bruce King、Edward E. Knaus

  DOI：10.1021/jm101403g

  日期：2011.3.10

  The carboxylic acid group of the anti-inflammatory (AI) drugs indomethacin, (S)-naproxen and ibuprofen was covalently linked via a two-carbon ethyl spacer to a sulfohydroxamic acid moiety (CH2CH2SO2NHOH) to furnish a group of hybrid ester prodrugs that release nitric oxide (NO) and nitroxyl (HNO). Biological data acquired for this hitherto unknown class of ethanesulfohydroxamic acid ester prodrugs showed (i) all compounds exhibited superior NO, but similar HNO, release properties relative to arylsulfohydroxamic acids, (ii) the (S)-naproxen and ibuprofen prodrug esters are more potent AI agents than their parent NSAID, (iii) the indomethacin prodrug ester, in contrast to indomethacin which is highly ulcerogenic, showed no visible stomach lesions [ulcer index (UI) = 0 for a 80 mu mol/kg oral dose] while retaining potent AI activity, and iv) that the indomethacin prodrug ester, unlike indomethacin which is an ulcerogenic selective COX-1 inhibitor, is a selective COX-2 inhibitor (COX-2 selectivity index = 184) devoid of ulcerogenicity that is attributed to its high COX-2 SI and/or ability to release cytoprotective NO.