5-Phenyl-2-indolylcarbonsaeuremethylester | 66616-70-4

• 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: 5-Phenyl-2-indolylcarbonsaeuremethylester
• 英文别名: methyl 5-phenyl-1H-indole-2-carboxylate；5-phenyl-indole-2-carboxylic acid methyl ester；5-Phenyl-2-carbomethoxyindole
• CAS: 66616-70-4
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: MKMFEQXKGCBGNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Phenyl-2-indolylcarbonsaeuremethylester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以99%的产率得到5-phenylindole-2-carboxylicacid
  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：

  3-甲基-4-硝基联苯 在 tin(II) chloride dihdyrate 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 5-Phenyl-2-indolylcarbonsaeuremethylester
  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

• 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
  申请人：ELM CO., LTD. 주식회사 이엘엠(120020276957) Corp. No ▼ 110111-2435439BRN ▼214-87-04493

  公开号：KR101505059B1

  公开（公告）日：2015-03-25

  본 발명은 유기 전기발광 소자에 사용되는 화합물 유도체와 이를 이용한 유기 전기발광 소자에 관한 것으로, 더욱 자세하게는 방향족 아민 유도체 화합물을 제조하고, 이를 유기 전기발광 소자의 정공전달물질로 사용하여 소자의 수명을 증가시키며, 발광 휘도와 발광 효율이 우수한 유기 전기발광 소자를 제공하는 것이다.

  本发明涉及用于有机电致发光器件的化合物衍生物以及利用其制备的有机电致发光器件，更具体地，涉及制备芳香胺衍生物化合物，并将其用作有机电致发光器件的正孔传输材料，以延长器件的寿命，并提供发光亮度和发光效率优异的有机电致发光器件。
• CYBOPOB N. N.; SAMSONIYA SH. A.; CHILIKIN L. G.; CHIKVAIDZE I. SH.; TURCH+, XIMIYA GETEROTSIKL. SOEDIN., 1978, HO 2, 217-224
  作者：CYBOPOB N. N.、 SAMSONIYA SH. A.、 CHILIKIN L. G.、 CHIKVAIDZE I. SH.、 TURCH+

  DOI：——

  日期：——