(E)-N-(1,3-benzodioxol-5-ylmethoxy)-1-(2-bromocyclopenten-1-yl)methanimine | 493021-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-N-(1,3-benzodioxol-5-ylmethoxy)-1-(2-bromocyclopenten-1-yl)methanimine
• CAS: 493021-65-1
• 化学式: C₁₄H₁₄BrNO₃
• 分子量: 324.174
• InChiKey: QATDGPCXSRNWIP-FRKPEAEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N-(1,3-benzodioxol-5-ylmethoxy)-1-(2-bromocyclopenten-1-yl)methanimine 在 potassium hydrogensulfate 、 oxone 、 四(三苯基膦)钯 、 sodium carbonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 24.0h， 生成 (E)-N-(1,3-benzodioxol-5-ylmethoxy)-1-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]methanimine
  参考文献：
  名称：

  (E)-[2-(4-Methylsulphonylphenyl)-1-cyclopentenyl-1-methyliden](arylmethyloxy)amines. Methyleneaminoxymethyl (MAOM) analogues of diarylcyclopentenyl cyclooxygenase-2 inhibitors: synthesis and biological properties

  摘要：

  The (E)-[2-(4-Methylsulphonylphenyl)-1-cyclopentenyl-1-methyliden](methyloxy)amine (5) and (arylmethyloxy)amines (6-12) were designed in order to verify the effects on the biological properties of the substitution of an aryl of selective diarylcyclopentenyl cyclooxygenase-2 (COX-2) inhibitors. of type 3 with a methyleneaminoxymethyl moiety (MAOMM). Compounds 5-12 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. The compound with the highest in vitro activity towards COX-2 (9) was also assayed in vivo for its antiinflammatory activity by means of the carrageenan-induced paw edema test in rats. Some of the new compounds showed an appreciable in vitro COX-2 inhibitory activity, with IC50 values in the muM (6,7,9,10,11) range. Compound 9 also exhibited an appreciable in vivo activity (29% inhibition at a dose of 30 mg kg(-1)) when administered intraperitoneally. The structural parameters of 9 were determined by X-ray crystallographic analysis. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01359-4
• 作为产物：
  描述：

  2-溴环戊烯-1-甲醛 、 3,4-(methylenedioxy)benzyloxyamine hydrochloride 以 氯仿 、 水 为溶剂， 反应 24.0h， 以91%的产率得到(E)-N-(1,3-benzodioxol-5-ylmethoxy)-1-(2-bromocyclopenten-1-yl)methanimine
  参考文献：
  名称：

  (E)-[2-(4-Methylsulphonylphenyl)-1-cyclopentenyl-1-methyliden](arylmethyloxy)amines. Methyleneaminoxymethyl (MAOM) analogues of diarylcyclopentenyl cyclooxygenase-2 inhibitors: synthesis and biological properties

  摘要：

  The (E)-[2-(4-Methylsulphonylphenyl)-1-cyclopentenyl-1-methyliden](methyloxy)amine (5) and (arylmethyloxy)amines (6-12) were designed in order to verify the effects on the biological properties of the substitution of an aryl of selective diarylcyclopentenyl cyclooxygenase-2 (COX-2) inhibitors. of type 3 with a methyleneaminoxymethyl moiety (MAOMM). Compounds 5-12 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. The compound with the highest in vitro activity towards COX-2 (9) was also assayed in vivo for its antiinflammatory activity by means of the carrageenan-induced paw edema test in rats. Some of the new compounds showed an appreciable in vitro COX-2 inhibitory activity, with IC50 values in the muM (6,7,9,10,11) range. Compound 9 also exhibited an appreciable in vivo activity (29% inhibition at a dose of 30 mg kg(-1)) when administered intraperitoneally. The structural parameters of 9 were determined by X-ray crystallographic analysis. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01359-4

文献信息

• (E)-[2-(4-Methylsulphonylphenyl)-1-cyclopentenyl-1-methyliden](arylmethyloxy)amines. Methyleneaminoxymethyl (MAOM) analogues of diarylcyclopentenyl cyclooxygenase-2 inhibitors: synthesis and biological properties
  作者：Aldo Balsamo、Isabella Coletta、Paolo Domiano、Angelo Guglielmotti、Carla Landolfi、Francesca Mancini、Claudio Milanese、Elisabetta Orlandini、Simona Rapposelli、Mario Pinza、Bruno Macchia

  DOI：10.1016/s0223-5234(02)01359-4

  日期：2002.5

  The (E)-[2-(4-Methylsulphonylphenyl)-1-cyclopentenyl-1-methyliden](methyloxy)amine (5) and (arylmethyloxy)amines (6-12) were designed in order to verify the effects on the biological properties of the substitution of an aryl of selective diarylcyclopentenyl cyclooxygenase-2 (COX-2) inhibitors. of type 3 with a methyleneaminoxymethyl moiety (MAOMM). Compounds 5-12 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. The compound with the highest in vitro activity towards COX-2 (9) was also assayed in vivo for its antiinflammatory activity by means of the carrageenan-induced paw edema test in rats. Some of the new compounds showed an appreciable in vitro COX-2 inhibitory activity, with IC50 values in the muM (6,7,9,10,11) range. Compound 9 also exhibited an appreciable in vivo activity (29% inhibition at a dose of 30 mg kg(-1)) when administered intraperitoneally. The structural parameters of 9 were determined by X-ray crystallographic analysis. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.