ethyl 3-[3-(3-ethoxy-3-oxopropyl)-4-[(E)-6-(4-methylsulfonylphenyl)hex-5-enoxy]benzoyl]benzoate | 128577-83-3

• 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: ethyl 3-[3-(3-ethoxy-3-oxopropyl)-4-[(E)-6-(4-methylsulfonylphenyl)hex-5-enoxy]benzoyl]benzoate
• CAS: 128577-83-3
• 化学式: C₃₄H₃₈O₈S
• 分子量: 606.737
• InChiKey: ZLYCAULXVKEZTI-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  43.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  113.04
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-[3-(3-ethoxy-3-oxopropyl)-4-[(E)-6-(4-methylsulfonylphenyl)hex-5-enoxy]benzoyl]benzoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以52%的产率得到5-(3-Carboxybenzoyl)-2-{[6-(4-methyl-sulfonylphenyl)-5-hexenyl]oxy}benzenepropanoic acid
  参考文献：
  名称：

  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 2. Structure-activity relationships of the lipophilic side chain

  摘要：

  A series of lipophilic benzophenone dicarboxylic acid derivatives were found to inhibit the binding of the potent chemotaxin leukotriene B4 (LTB4) to its receptor on intact human neutrophils. Activity at the LTB4 receptor was determined by using a [3H]LTB4-binding assay. The structure-activity relationship for the lipophilic side chain was systematically investigated. Compounds with n-alkyl side chains of varying lengths were prepared and tested. Best inhibition of [3H]LTB4 binding was observed with the n-decyl derivative. Analogues with alkyl chains terminated with an aromatic ring showed improved activity. The 6-phenylhexyl side chain was optimal. Substitution on the terminal aromatic ring was also evaluated. Methoxyl, methylsulfinyl, and methyl substituents greatly enhanced the activity of the compound. For a given substituent, the para isomer had the best activity. Thus the nature of the lipophilic side chain can greatly influence the ability of the compounds to inhibit the binding of LTB4 to its receptor on intact human neutrophils. The most active compound from this series, 84 (LY223982), bound to the LTB4 receptor with an affinity approaching that of the agonist.

  DOI：

  10.1021/jm00172a020
• 作为产物：
  描述：

  4-(甲基巯基)苯甲醛 在 lithium aluminium tetrahydride 、 sodium hydride 、 三乙胺 、 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 ethyl 3-[3-(3-ethoxy-3-oxopropyl)-4-[(E)-6-(4-methylsulfonylphenyl)hex-5-enoxy]benzoyl]benzoate
  参考文献：
  名称：

  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 2. Structure-activity relationships of the lipophilic side chain

  摘要：

  A series of lipophilic benzophenone dicarboxylic acid derivatives were found to inhibit the binding of the potent chemotaxin leukotriene B4 (LTB4) to its receptor on intact human neutrophils. Activity at the LTB4 receptor was determined by using a [3H]LTB4-binding assay. The structure-activity relationship for the lipophilic side chain was systematically investigated. Compounds with n-alkyl side chains of varying lengths were prepared and tested. Best inhibition of [3H]LTB4 binding was observed with the n-decyl derivative. Analogues with alkyl chains terminated with an aromatic ring showed improved activity. The 6-phenylhexyl side chain was optimal. Substitution on the terminal aromatic ring was also evaluated. Methoxyl, methylsulfinyl, and methyl substituents greatly enhanced the activity of the compound. For a given substituent, the para isomer had the best activity. Thus the nature of the lipophilic side chain can greatly influence the ability of the compounds to inhibit the binding of LTB4 to its receptor on intact human neutrophils. The most active compound from this series, 84 (LY223982), bound to the LTB4 receptor with an affinity approaching that of the agonist.

  DOI：

  10.1021/jm00172a020

文献信息

• GAPINSKI, D. MARK;MALLETT, BARBARA E.;FROELICH, LARRY L.;JACKSON, WILLIAM+, J. MED. CHEM., 33,(1990) N0, C. 2807-2813
  作者：GAPINSKI, D. MARK、MALLETT, BARBARA E.、FROELICH, LARRY L.、JACKSON, WILLIAM+

  DOI：——

  日期：——