methyl 6-amino-3-bromo-2-(2-(tert-butoxy)-2-oxoethoxy)benzoate | 943138-78-1

• 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: methyl 6-amino-3-bromo-2-(2-(tert-butoxy)-2-oxoethoxy)benzoate
• CAS: 943138-78-1
• 化学式: C₁₄H₁₈BrNO₅
• 分子量: 360.205
• InChiKey: PBHAUOLBTSFGQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  87.85
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 6-amino-3-bromo-2-(2-(tert-butoxy)-2-oxoethoxy)benzoate 在 四(三苯基膦)钯 吡啶 、 cesium fluoride 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 methyl 2-(2-(tert-butoxy)-2-oxoethoxy)-6-((4-fluorophenyl)sulfonamido)-3-vinylbenzoate
  参考文献：
  名称：

  Lead optimization of methionine aminopeptidase-2 (MetAP2) inhibitors containing sulfonamides of 5,6-disubstituted anthranilic acids

  摘要：

  A series of aryl sulfonamides of 5,6-disubstituted anthranilic acids were identified as potent inhibitors of methionine aminopeptidase-2 (MetAP2). Small alkyl groups and 3-furyl were tolerated at the 5-position of anthranilic acid, while -OCH3, CH3, and Cl were found optimal for the 6-position. Placement of 2-aminoethoxy group at the 6-position enabled interaction with the second Mn2+ but did not result in enhancement in potency. Introduction of a tertiary amino moiety at the ortho-position of the sulfonyl phenyl ring gave reduced protein binding and improved cellular activity, but led to lower oral bioavailability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.062
• 作为产物：
  描述：

  6-bromo-5-hydroxy-2H-3,1-benzoxazine-2,4(1H)-dione 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 methyl 6-amino-3-bromo-2-(2-(tert-butoxy)-2-oxoethoxy)benzoate
  参考文献：
  名称：

  Lead optimization of methionine aminopeptidase-2 (MetAP2) inhibitors containing sulfonamides of 5,6-disubstituted anthranilic acids

  摘要：

  A series of aryl sulfonamides of 5,6-disubstituted anthranilic acids were identified as potent inhibitors of methionine aminopeptidase-2 (MetAP2). Small alkyl groups and 3-furyl were tolerated at the 5-position of anthranilic acid, while -OCH3, CH3, and Cl were found optimal for the 6-position. Placement of 2-aminoethoxy group at the 6-position enabled interaction with the second Mn2+ but did not result in enhancement in potency. Introduction of a tertiary amino moiety at the ortho-position of the sulfonyl phenyl ring gave reduced protein binding and improved cellular activity, but led to lower oral bioavailability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.062