3-氨基-5-溴-2-甲氧基苯甲酸甲酯 | 926069-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氨基-5-溴-2-甲氧基苯甲酸甲酯
• 英文名称: 3-amino-5-bromo-2-methoxy-benzoic acid methyl ester
• 英文别名: Methyl 3-amino-5-bromo-2-methoxybenzoate
• CAS: 926069-76-3
• 化学式: C₉H₁₀BrNO₃
• 分子量: 260.087
• InChiKey: KQZUSVNTJVCFBU-UHFFFAOYSA-N

物化性质

• 沸点：
  364.3±37.0 °C(Predicted)
• 密度：
  1.531±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  3-氨基-5-溴-2-甲氧基苯甲酸甲酯 在 吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 生成 3-cyclopropylsulfonamino-2-methoxy-5-(4-morpholinoquinazolin-6-yl)benzamide
  参考文献：
  名称：

  Discovery of 2-methoxy-3-phenylsulfonamino-5-(quinazolin-6-yl or quinolin-6-yl)benzamides as novel PI3K inhibitors and anticancer agents by bioisostere

  摘要：

  2-Substituted-3-sulfonamino-5-(quinazolin-6-yl or quinolin-6-yl)benzamides have been proposed as novel structures of PI3K inhibitors and anticancer agents based on bioisostere. In the present study, 2-substituted-3-sulfonamino-5-(4-morpholinoquinazolin-6-yl)benzamides and 2-methoxy-3-sulfonamino-5-(4-morpholinoquinolin-6-yl)benzamides were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against four human cancer cell lines, including A549, HCT-116, U-87 MG and KB. The SAR of the title compounds was preliminarily discussed. Compound 1a with potent antiproliferative activity was tested for its inhibitory activity against MK and mTOR and its effect on the AKT and p-AKT(473). The anticancer effect of la was evaluated in established nude mice U-87 MG xenograft model. The results suggest that compound la can significantly inhibit PI3K/AKT/mTOR pathway and tumor growth. These findings strongly support the assumption that title compounds are potent PI3K inhibitors and anticancer agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.053
• 作为产物：
  描述：

  5-溴水杨酸 在 氢氧化钾 、 硫酸 、 硝酸 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 9.5h， 生成 3-氨基-5-溴-2-甲氧基苯甲酸甲酯
  参考文献：
  名称：

  加强杂合肽中的周期性二级结构：一种新型的包含周期性的γ-转体的杂种Foldamer。

  摘要：

  本说明描述了新型混合型折叠式折叠器的设计，合成和构象研究，该折叠式折叠器采用了确定的紧凑的三维结构，该结构由折叠式折叠器成分的特殊构象特性共同决定。这种从头设计的折叠剂的显着特征是它能够显示出通过分子内氢键稳定的周期性γ转构象的能力。通过单晶X射线研究，溶液态NMR和从头算MO理论在HF / 6-31G *水平进行的构象研究强有力地支持了二肽和四肽折叠子中γ转角基序的普遍存在。大概是通过分叉的氢键稳定在固态和溶液态。

  DOI：

  10.1021/jo062032w

文献信息

• Discovery of 2-methoxy-3-phenylsulfonamino-5-(quinazolin-6-yl or quinolin-6-yl)benzamides as novel PI3K inhibitors and anticancer agents by bioisostere
  作者：Teng Shao、Juan Wang、Jian-Gang Chen、Xiao-Meng Wang、Huan Li、Yi-Ping Li、Yan Li、Guang-De Yang、Qi-Bing Mei、San-Qi Zhang

  DOI：10.1016/j.ejmech.2014.01.053

  日期：2014.3

  2-Substituted-3-sulfonamino-5-(quinazolin-6-yl or quinolin-6-yl)benzamides have been proposed as novel structures of PI3K inhibitors and anticancer agents based on bioisostere. In the present study, 2-substituted-3-sulfonamino-5-(4-morpholinoquinazolin-6-yl)benzamides and 2-methoxy-3-sulfonamino-5-(4-morpholinoquinolin-6-yl)benzamides were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against four human cancer cell lines, including A549, HCT-116, U-87 MG and KB. The SAR of the title compounds was preliminarily discussed. Compound 1a with potent antiproliferative activity was tested for its inhibitory activity against MK and mTOR and its effect on the AKT and p-AKT(473). The anticancer effect of la was evaluated in established nude mice U-87 MG xenograft model. The results suggest that compound la can significantly inhibit PI3K/AKT/mTOR pathway and tumor growth. These findings strongly support the assumption that title compounds are potent PI3K inhibitors and anticancer agents. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Enforcing Periodic Secondary Structures in Hybrid Peptides:  A Novel Hybrid Foldamer Containing Periodic γ-Turn Motifs
  作者：Pranjal K. Baruah、N. K. Sreedevi、Rajesh Gonnade、Sapna Ravindranathan、Krishnan Damodaran、Hans-Jörg Hofmann、Gangadhar J. Sanjayan

  DOI：10.1021/jo062032w

  日期：2007.1.1

  synthesis, and conformational studies of a novel hybrid foldamer that adopts a definite compact, three-dimensional structure determined by a combined effect of the special conformational properties of the foldamer constituents. The striking feature of this de novo designed foldamer is its ability to display periodic γ-turn conformations stabilized by intramolecular hydrogen bonds. Conformational investigations

  本说明描述了新型混合型折叠式折叠器的设计，合成和构象研究，该折叠式折叠器采用了确定的紧凑的三维结构，该结构由折叠式折叠器成分的特殊构象特性共同决定。这种从头设计的折叠剂的显着特征是它能够显示出通过分子内氢键稳定的周期性γ转构象的能力。通过单晶X射线研究，溶液态NMR和从头算MO理论在HF / 6-31G *水平进行的构象研究强有力地支持了二肽和四肽折叠子中γ转角基序的普遍存在。大概是通过分叉的氢键稳定在固态和溶液态。