3-[1-(4-Chloro-benzyl)-3-methyl-5-trifluoromethanesulfonyloxy-1H-indol-2-yl]-2,2-dimethyl-propionic acid methyl ester | 862555-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[1-(4-Chloro-benzyl)-3-methyl-5-trifluoromethanesulfonyloxy-1H-indol-2-yl]-2,2-dimethyl-propionic acid methyl ester
• CAS: 862555-21-3
• 化学式: C₂₃H₂₃ClF₃NO₅S
• 分子量: 517.954
• InChiKey: NOSUGFJIEBEFGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.6
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-[1-(4-Chloro-benzyl)-3-methyl-5-trifluoromethanesulfonyloxy-1H-indol-2-yl]-2,2-dimethyl-propionic acid methyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium hydroxide 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-[1-(4-Chloro-benzyl)-3-methyl-5-phenyl-1H-indol-2-yl]-2,2-dimethyl-propionic acid
  参考文献：
  名称：

  Inhibitors of the inducible microsomal prostaglandin E2 synthase (mPGES-1) derived from MK-886

  摘要：

  A series of potent and selective inhibitors of the inducible microsomal PGE(2) synthase (mPGES-1) has been developed based on the indole FLAP inhibitor MK-886. Compounds 23 and 30 inhibit mPGES-1 with potencies in the low nanomolar range and with selectivities of at least 100-fold compared to their inhibition of mPGES-2, thromboxane synthase and binding affinity to FLAP. They also block the production of PGE(2) in cell based assays but with a decreased potency and more limited selectivity compared to the enzyme assays. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.027
• 作为产物：
  描述：

  4-甲氧基苯肼盐酸盐 在 三溴化硼 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 叔丁醇 为溶剂， 反应 30.0h， 生成 3-[1-(4-Chloro-benzyl)-3-methyl-5-trifluoromethanesulfonyloxy-1H-indol-2-yl]-2,2-dimethyl-propionic acid methyl ester
  参考文献：
  名称：

  Inhibitors of the inducible microsomal prostaglandin E2 synthase (mPGES-1) derived from MK-886

  摘要：

  A series of potent and selective inhibitors of the inducible microsomal PGE(2) synthase (mPGES-1) has been developed based on the indole FLAP inhibitor MK-886. Compounds 23 and 30 inhibit mPGES-1 with potencies in the low nanomolar range and with selectivities of at least 100-fold compared to their inhibition of mPGES-2, thromboxane synthase and binding affinity to FLAP. They also block the production of PGE(2) in cell based assays but with a decreased potency and more limited selectivity compared to the enzyme assays. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.027