(2Z,4E)-2-Benzylsulfanyl-5-hydroxy-hexa-2,4-dienedioic acid diethyl ester | 122830-59-5

• 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: (2Z,4E)-2-Benzylsulfanyl-5-hydroxy-hexa-2,4-dienedioic acid diethyl ester
• 英文别名: Diethyl 5-benzylthio-2-hydroxy-2,4-hexadienedioate；diethyl 2-benzylsulfanyl-5-hydroxyhexa-2,4-dienedioate
• CAS: 122830-59-5
• 化学式: C₁₇H₂₀O₅S
• 分子量: 336.409
• InChiKey: BPWXUGSFTGIXBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (benzylthio)acetate 在 盐酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.83h， 生成 (2Z,4E)-2-Benzylsulfanyl-5-hydroxy-hexa-2,4-dienedioic acid diethyl ester
  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

• Alkadiene derivatives, and pharmaceutical compositions containing them
  申请人：Rhone-Poulenc Sante

  公开号：US04971979A1

  公开（公告）日：1990-11-20

  Substituted alkadienes of formula: ##STR1## in which R.sub.1 is hydroxy or acetoxy, R.sub.2 is hydrogen, carboxy, alkoxycarbonyl, phenyl or benzoyl, and R.sub.3 is alkylthio or alkoxy and R.sub.4 is naphthoyl or optionally substituted benzoyl, or R.sub.3 is alkoxycarbonyl, cycloalkyloxycarbonyl or cyano and R.sub.4 is alkyl, naphthyl, optionally substituted phenyl, alkylthio, naphthylmethanethio, optionally substituted benzylthio, optionally substituted phenylthio, naphthylthio, phenethylthio or allylthio, or R.sub.3 and R.sub.4 form, with the carbon atom to which they are attached, a ring-system of formula: ##STR2## in which R.sub.5 is hydrogen or alkoxy and X is methylene or S inhibit 5-lipoxygenase and are useful, for example, as anti-inflammatories.

  式子为：##STR1## 其中 R.sub.1 为羟基或乙酰氧基，R.sub.2 为氢、羧基、烷氧羰基、苯基或苯甲酰基，R.sub.3 为烷基硫醇或烷氧基，R.sub.4 为萘甲酰基或可选的取代苯甲酰基，或 R.sub.3 为烷氧羰基、环烷氧羰基或氰基，R.sub.4 为烷基、萘基、可选的取代苯基、烷基硫醇、萘基甲硫、可选的取代苯基甲硫、可选的取代苯基硫、萘基硫、苯乙基硫或烯丙基硫，或 R.sub.3 和 R.sub.4 与它们连接的碳原子形成一个环式系统，其式子为：##STR2## 其中 R.sub.5 为氢或烷氧基，X 为亚甲基或硫，这些化合物能抑制5-脂氧酶，例如作为抗炎药物。
• Alkadiene derivatives, their preparation, and pharmaceutical
  申请人：Rhone-Poulenc Sante

  公开号：US04886835A1

  公开（公告）日：1989-12-12

  Substituted alkadienes of the formula: ##STR1## in which R.sub.1 is hydroxy or acetoxy, R.sub.2 is hydrogen, carboxy, alkoxycarbonyl, phenyl or benzoyl, and R.sub.3 is alkylthio or alkoxy and R.sub.4 is naphthoyl or optionally substituted benzoyl, or R.sub.3 is alkoxycarbonyl, cycloalkyloxycarbonyl or cyano and R.sub.4 is alkyl, naphthyl, optionally substituted phenyl, alkylthio, naphthylmethanethio, optionally substituted benzylthio, optionally substituted phenylthio, naphthylthio, phenethylthio or allylthio, or R.sub.3 and R.sub.4 form, with the carbon atom to which they are attached, a ring-system of formula: ##STR2## in which R.sub.5 is hydrogen or alkoxy and X is methylene or S inhibit 5-lipoxygenase and are useful, for example, as anti-inflammatories.

  公式为：##STR1##的取代烯烃，其中R.sub.1是羟基或乙酰氧基，R.sub.2是氢，羧基，烷氧羰基，苯基或苯甲酰基，R.sub.3是烷基硫醇或烷氧基，R.sub.4是萘甲酰基或可选取代苯甲酰基，或R.sub.3是烷氧羰基，环烷氧羰基或氰基，R.sub.4是烷基，萘基，可选取代苯基，烷基硫醇，萘基甲硫基，可选取代苯基甲硫基，可选取代苯基硫基，萘基硫基，苯乙基硫基或烯丙基硫基，或R.sub.3和R.sub.4与它们附着的碳原子形成一个环系统，其化学式为：##STR2##其中R.sub.5是氢或烷氧基，X是亚甲基或硫，抑制5-脂氧酶并且可用作例如抗炎药。