methyl 3-(4-bromo-2-nitrophenyl)-2-oxopropanoate | 1269802-80-3

• 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 3-(4-bromo-2-nitrophenyl)-2-oxopropanoate
• CAS: 1269802-80-3
• 化学式: C₁₀H₈BrNO₅
• 分子量: 302.081
• InChiKey: LADPAPJGLMYLNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-bromo-2-nitrophenyl)-2-oxopropanoate 在 tin(II) chloride dihdyrate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 生成 6-Brom-1-hydroxy-indol-2-carbonsaeure
  参考文献：
  名称：

  Discovery of N-Hydroxyindole-Based Inhibitors of Human Lactate Dehydrogenase Isoform A (LDH-A) as Starvation Agents against Cancer Cells

  摘要：

  Highly invasive tumor cells are characterized by a metabolic switch, known as the Warburg effect, from "normal" oxidative phosphorylation to increased glycolysis even under. sufficiently oxygenated conditions. This dependence on glycolysis also confers a growth advantage to cells present in hypoxic regions of the tumor. One of the key enzymes involved in glycolysis, the muscle isoform of lactate dehydrogenase (LDH-A), is overexpressed by metastatic cancer cells and is linked to the vitality of tumors in hypoxia. This enzyme may be considered as a potential target for new anticancer agents, since its inhibition cuts cancer energetic and anabolic supply, thus reducing the metastatic and invasive potential of cancer cells. We have discovered new and efficient N-hydroxyindole-based inhibitors of LDH-A, which are isoform-selective (over LDH-B) and competitive with both the substrate (pyruvate) and the cofactor (NADH). The antiproliferative activity of these compounds was confirmed on a series of cancer cell lines, and they proved to be particularly effective under hypoxic conditions. Moreover, NMR experiments showed that these compounds are able to reduce the glucose-to-lactate conversion inside the cell.

  DOI：

  10.1021/jm101007q
• 作为产物：
  描述：

  草酸二甲酯 、 4-溴-2-硝基甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以78%的产率得到methyl 3-(4-bromo-2-nitrophenyl)-2-oxopropanoate
  参考文献：
  名称：

  Discovery of N-Hydroxyindole-Based Inhibitors of Human Lactate Dehydrogenase Isoform A (LDH-A) as Starvation Agents against Cancer Cells

  摘要：

  Highly invasive tumor cells are characterized by a metabolic switch, known as the Warburg effect, from "normal" oxidative phosphorylation to increased glycolysis even under. sufficiently oxygenated conditions. This dependence on glycolysis also confers a growth advantage to cells present in hypoxic regions of the tumor. One of the key enzymes involved in glycolysis, the muscle isoform of lactate dehydrogenase (LDH-A), is overexpressed by metastatic cancer cells and is linked to the vitality of tumors in hypoxia. This enzyme may be considered as a potential target for new anticancer agents, since its inhibition cuts cancer energetic and anabolic supply, thus reducing the metastatic and invasive potential of cancer cells. We have discovered new and efficient N-hydroxyindole-based inhibitors of LDH-A, which are isoform-selective (over LDH-B) and competitive with both the substrate (pyruvate) and the cofactor (NADH). The antiproliferative activity of these compounds was confirmed on a series of cancer cell lines, and they proved to be particularly effective under hypoxic conditions. Moreover, NMR experiments showed that these compounds are able to reduce the glucose-to-lactate conversion inside the cell.

  DOI：

  10.1021/jm101007q

文献信息

• Chemical encoding technology for combinatorial synthesis
  申请人：——

  公开号：US20040146941A1

  公开（公告）日：2004-07-29

  A chemical tag can include a core and a plurality of substituents attached directly to the core. The substituents of each chemical tag form a subset of a closed set of possible substituents. The tag can be used to track an object.

  化学标签可包括一个核心和直接连接到核心上的多个取代基。每个化学标签的取代基都是可能的取代基封闭集合的子集。标签可用于跟踪物体。
• [EN] CHEMICAL ENCODING TECHNOLOGY FOR COMBINATORIAL SYNTHESIS<br/>[FR] TECHNOLOGIE DE CODAGE CHIMIQUE POUR SYNTHESE COMBINATOIRE
  申请人：ZHANG BILIANG

  公开号：WO2004041752A2

  公开（公告）日：2004-05-21

  A chemical tag can include a core and a plurality of substituents attached directly to the core. The substituents of each chemical tag form a subset of a closed set of possible substituents. The tag can be used to track an object.
• A convenient synthetic approach to 11H-indolo[3,2-c]quinoline framework via Friedlander condensation and Cadogan cyclization
  作者：R. Li、S. Liu

  DOI：10.24820/ark.5550190.p012.176

  日期：——