(E)-1-[2-(4-methylsulfanylphenyl)cyclopenten-1-yl]-N-phenylmethoxyethanimine | 488759-35-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-1-[2-(4-methylsulfanylphenyl)cyclopenten-1-yl]-N-phenylmethoxyethanimine
• CAS: 488759-35-9
• 化学式: C₂₁H₂₃NOS
• 分子量: 337.486
• InChiKey: DMNNKGBEESDIIT-CJLVFECKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-[2-(4-methylsulfanylphenyl)cyclopenten-1-yl]-N-phenylmethoxyethanimine 在 Oxone 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 以82%的产率得到(E)-1-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]-N-phenylmethoxyethanimine
  参考文献：
  名称：

  Aryl-substituted methyleneaminoxymethyl (MAOM) analogues of diarylcyclopentenyl cyclooxygenase-2 inhibitors: effects of some structural modifications on their biological properties

  摘要：

  The (E)-[2-(4-aminosulfonylphenyl)-1-cyclopentenyl-1-methyliden]-(arylmethyloxy)amines (6a,b), which are the sulfonamidic analogues of the previously described methylsulfonyl derivatives 5a,b, and their corresponding sulfides (7a,b) and sulfoxides (8a,b) were synthesised in order to obtain information about the role played by these different sulphur-containing groups in the cyclooxygenase-2 inhibitory activity of this class of compounds. In addition, other chemical manipulations concerning the oxime-ether substituent of this type of derivatives were affected by preparing compounds 9a,b, which present a methyl group on the oximic carbon of the oxime-ether chain of 50, and compounds 10 and 11, in which the atomic sequence (C=NOCH2) of the MAOMM of 8b and 5b, respectively, is inverted. Compounds 6-11 were tested in vitro for their inhibitory activity towards COX-1 and COX-2 by measuring prostaglandin E2 (PGE2) production in U937 cell lines and activated J774.2 macrophages, respectively. Some of the new compounds showed an appreciable in vitro COX-2 inhibitory activity, with IC50 values in the muM (7a,b, 8a and 9b) or sub-ELM (8b) range. This last compound was also assayed in vivo for its antiinflammatory activity by means of the carrageenan-induced paw edema test in rats. No inhibitory effects were detected up to dose of 30 mg kg(-1) orally administered. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01385-5
• 作为产物：
  描述：

  1-(2-chlorocyclopent-1-enyl)ethanone 在 tris(dibenzylideneacetone)dipalladium (0) 三环己基膦 作用下， 以 1,4-二氧六环 、 氯仿 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 (E)-1-[2-(4-methylsulfanylphenyl)cyclopenten-1-yl]-N-phenylmethoxyethanimine
  参考文献：
  名称：

  Aryl-substituted methyleneaminoxymethyl (MAOM) analogues of diarylcyclopentenyl cyclooxygenase-2 inhibitors: effects of some structural modifications on their biological properties

  摘要：

  The (E)-[2-(4-aminosulfonylphenyl)-1-cyclopentenyl-1-methyliden]-(arylmethyloxy)amines (6a,b), which are the sulfonamidic analogues of the previously described methylsulfonyl derivatives 5a,b, and their corresponding sulfides (7a,b) and sulfoxides (8a,b) were synthesised in order to obtain information about the role played by these different sulphur-containing groups in the cyclooxygenase-2 inhibitory activity of this class of compounds. In addition, other chemical manipulations concerning the oxime-ether substituent of this type of derivatives were affected by preparing compounds 9a,b, which present a methyl group on the oximic carbon of the oxime-ether chain of 50, and compounds 10 and 11, in which the atomic sequence (C=NOCH2) of the MAOMM of 8b and 5b, respectively, is inverted. Compounds 6-11 were tested in vitro for their inhibitory activity towards COX-1 and COX-2 by measuring prostaglandin E2 (PGE2) production in U937 cell lines and activated J774.2 macrophages, respectively. Some of the new compounds showed an appreciable in vitro COX-2 inhibitory activity, with IC50 values in the muM (7a,b, 8a and 9b) or sub-ELM (8b) range. This last compound was also assayed in vivo for its antiinflammatory activity by means of the carrageenan-induced paw edema test in rats. No inhibitory effects were detected up to dose of 30 mg kg(-1) orally administered. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01385-5