2-quinolin-4-ylamino-benzoic acid | 52180-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-quinolin-4-ylamino-benzoic acid
• 英文别名: N-(4-Chinolyl)-anthranilsaeure；N-(4-Quinolinyl)anthranilic acid；2-(quinolin-4-ylamino)benzoic acid
• CAS: 52180-97-9
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: VAYWXCMEIWUYBK-UHFFFAOYSA-N

物化性质

• 沸点：
  459.2±30.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  N⁴-(3-aminophenyl)-6-methylpyrimidine-2,4-diamine 、 2-quinolin-4-ylamino-benzoic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以74%的产率得到N-(3-(2-amino-6-methylpyrimidin-4-ylamino)phenyl)-2-(quinolin-4-ylamino)benzamide
  参考文献：
  名称：

  Selective Non-nucleoside Inhibitors of Human DNA Methyltransferases Active in Cancer Including in Cancer Stem Cells

  摘要：

  DNA methyltransferases (DNMTs) are important enzymes involved in epigenetic control of gene expression and represent valuable targets in cancer chemotherapy. A number of nucleoside DNMT inhibitors (DNMTi) have been studied in cancer, including in cancer stem cells, and two of them (azacytidine and decitabine) have been approved for treatment of myelodysplastic syndromes. However, only a few non-nucleoside DNMTi have been identified so far, and even fewer have been validated in cancer. Through a process of hit-to-lead optimization, we report here the discovery of compound 5 as a potent non-nucleoside DNMTi that is also selective toward other Ado Met-dependent protein methyltransferases. Compound 5 was potent at single-digit micromolar concentrations against a panel of cancer cells and was less toxic in peripheral blood mononuclear cells than two other compounds tested. In mouse medulloblastoma stem cells, 5 inhibited cell growth, whereas related compound 2 showed high cell differentiation. To the best of our knowledge, 2 and 5 are the first non-nucleoside DNMTi tested in a cancer stem cell line.

  DOI：

  10.1021/jm4012627
• 作为产物：
  描述：

  2-氨基苯甲酸乙酯 在 盐酸 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-quinolin-4-ylamino-benzoic acid
  参考文献：
  名称：

  Selective Non-nucleoside Inhibitors of Human DNA Methyltransferases Active in Cancer Including in Cancer Stem Cells

  摘要：

  DNA methyltransferases (DNMTs) are important enzymes involved in epigenetic control of gene expression and represent valuable targets in cancer chemotherapy. A number of nucleoside DNMT inhibitors (DNMTi) have been studied in cancer, including in cancer stem cells, and two of them (azacytidine and decitabine) have been approved for treatment of myelodysplastic syndromes. However, only a few non-nucleoside DNMTi have been identified so far, and even fewer have been validated in cancer. Through a process of hit-to-lead optimization, we report here the discovery of compound 5 as a potent non-nucleoside DNMTi that is also selective toward other Ado Met-dependent protein methyltransferases. Compound 5 was potent at single-digit micromolar concentrations against a panel of cancer cells and was less toxic in peripheral blood mononuclear cells than two other compounds tested. In mouse medulloblastoma stem cells, 5 inhibited cell growth, whereas related compound 2 showed high cell differentiation. To the best of our knowledge, 2 and 5 are the first non-nucleoside DNMTi tested in a cancer stem cell line.

  DOI：

  10.1021/jm4012627

文献信息

• Design, synthesis, and biological activity of platinum-benz[c]acridine hybrid agents and methods associated therewith
  申请人：WAKE FOREST UNIVERSITY

  公开号：US10023599B2

  公开（公告）日：2018-07-17

  The present invention relates to the compounds of formula I, pharmaceutically acceptable salts, and solvates thereof: wherein the various substituents are as defined herein. The compounds, solvates and salts thereof of Formula I are effective as anti-cancer compounds.

  本发明涉及式 I 的化合物、药学上可接受的盐及其溶液： 其中各种取代基如本文所定义。式 I 的化合物、其溶液和盐作为抗癌化合物是有效的。
• 含有吗啉丙基的[(喹啉-4-基)氨基]苯甲酰胺类化合物及其制备与应用
  申请人：沈阳药科大学

  公开号：CN114890946A

  公开（公告）日：2022-08-12

  本发明的含有吗啉丙基的[(喹啉‑4‑基)氨基]苯甲酰胺类化合物及其制备与应用，属于医药技术领域。具体为结构式如式I所示的含有吗啉丙基的[(喹啉‑4‑基)氨基]苯甲酰胺类化合物、其前体药物和药物活性代谢物和药学上可接受的盐，其中R如权利要求书和说明书中所述。相应的含有吗啉丙基的[(喹啉‑4‑基)氨基]苯甲酰胺类化合物以及该类化合物药学上适用的酸和药学上可接受的盐可以与现有药物合并或单独使用作为流感病毒抑制剂，用于治疗流感，尤其是对各种A型流感具有较好的疗效。
• Design, Synthesis, and Biological Activity of Platinum-benz[c]acridine Hybrid Agents and Methods Associated Therewith
  申请人：WAKE FOREST UNIVERSITY

  公开号：US20170081351A1

  公开（公告）日：2017-03-23

  The present invention relates to the compounds of formula I, pharmaceutically acceptable salts, and solvates thereof: wherein the various substituents are as defined herein. The compounds, solvates and salts thereof of Formula I are effective as anti-cancer compounds.
• US3935229A
  申请人：——

  公开号：US3935229A

  公开（公告）日：1976-01-27
• US4017623A
  申请人：——

  公开号：US4017623A

  公开（公告）日：1977-04-12