diethyl 2-hydroxy-5-(ethylthio)-2(Z),4(Z)-hexadienedioate | 129363-81-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: diethyl 2-hydroxy-5-(ethylthio)-2(Z),4(Z)-hexadienedioate
• 英文别名: diethyl 2-hydroxy-5-ethylthio-2,4-hexadienedioate；diethyl (2Z,4Z)-2-ethylsulfanyl-5-hydroxyhexa-2,4-dienedioate
• CAS: 129363-81-1
• 化学式: C₁₂H₁₈O₅S
• 分子量: 274.338
• InChiKey: FGNZLBSNLAVVFZ-XOHWUJONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2-hydroxy-5-(ethylthio)-2(Z),4(Z)-hexadienedioate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以38%的产率得到2-hydroxy-5-(ethylthio)-2,4-hexadienedioic acid
  参考文献：
  名称：

  Penta- and hexadienoic acid derivatives: a novel series of 5-lipoxygenase inhibitors

  摘要：

  The synthesis of a series of pentadienoic and hexadienoic acid derivatives is reported. These compounds were tested as inhibitors of 5-lipoxygenase (5 LO) and cyclooxygenase (CO) in vitro and as inhibitors of arachidonic acid (AA) induced ear edema in mice in vivo. Their potency is compared with that of the standard inhibitors nafazatrom, BW 755C, NDGA, KME4, quercetine, and L 652,243. The most potent compound in vivo, diethyl 2-hydroxy-5-(ethylthio)-2(Z),4(Z)-hexadienedioate (20) inhibited AA-induced ear edema when administered topically or orally, with an ED50 value of 0.01 mg/ear and 20 mg/kg, respectively. Among the standard compounds tested, L 652,243 was the most active compound in this test with an ED50 value of 0.01 mg/ear and 1 mg/kg po, but unlike this compound, 20 is a selective inhibitor of 5-LO (IC50 = 2 microM) without any significant activity against CO (IC50 greater than 50 microM). Most of the other compounds in this series are also selective 5-LO inhibitors.

  DOI：

  10.1021/jm00172a010
• 作为产物：
  描述：

  乙硫基乙酸乙酯 在 盐酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.83h， 生成 diethyl 2-hydroxy-5-(ethylthio)-2(Z),4(Z)-hexadienedioate
  参考文献：
  名称：

  Penta- and hexadienoic acid derivatives: a novel series of 5-lipoxygenase inhibitors

  摘要：

  The synthesis of a series of pentadienoic and hexadienoic acid derivatives is reported. These compounds were tested as inhibitors of 5-lipoxygenase (5 LO) and cyclooxygenase (CO) in vitro and as inhibitors of arachidonic acid (AA) induced ear edema in mice in vivo. Their potency is compared with that of the standard inhibitors nafazatrom, BW 755C, NDGA, KME4, quercetine, and L 652,243. The most potent compound in vivo, diethyl 2-hydroxy-5-(ethylthio)-2(Z),4(Z)-hexadienedioate (20) inhibited AA-induced ear edema when administered topically or orally, with an ED50 value of 0.01 mg/ear and 20 mg/kg, respectively. Among the standard compounds tested, L 652,243 was the most active compound in this test with an ED50 value of 0.01 mg/ear and 1 mg/kg po, but unlike this compound, 20 is a selective inhibitor of 5-LO (IC50 = 2 microM) without any significant activity against CO (IC50 greater than 50 microM). Most of the other compounds in this series are also selective 5-LO inhibitors.

  DOI：

  10.1021/jm00172a010

文献信息

• MALLERON, J. L.;ROUSSEL, G.;GUEREMY, G.;PONSINET, G.;ROBIN, J. L.;TERLAIN+, J. MED. CHEM., 33,(1990) N0, C. 2744-2749
  作者：MALLERON, J. L.、ROUSSEL, G.、GUEREMY, G.、PONSINET, G.、ROBIN, J. L.、TERLAIN+

  DOI：——

  日期：——
• US4886835A
  申请人：——

  公开号：US4886835A

  公开（公告）日：1989-12-12
• US4971979A
  申请人：——

  公开号：US4971979A

  公开（公告）日：1990-11-20