1-Methyl-2-ethylperimidin | 66308-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-Methyl-2-ethylperimidin
• 英文别名: 2-ethyl-1-methyl-1H-perimidine；1-Methyl-2-ethylperimidine；2-ethyl-1-methylperimidine
• CAS: 66308-58-5
• 化学式: C₁₄H₁₄N₂
• 分子量: 210.279
• InChiKey: JOANXWUWBTYLSO-UHFFFAOYSA-N

物化性质

• 熔点：
  107 °C
• 沸点：
  377.7±25.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Methyl-2-ethylperimidin 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 sodium nitrite 、 过氧化苯甲酰 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 9-bromo-2-ethyl-1-methyl-1H-perimidine-7,8-dione
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel perimidine o-quinone derivatives as non-intercalative topoisomerase II catalytic inhibitors

  摘要：

  For the development of novel anticancer agents, we designed and synthesized a total of 37 perimidine o-quinone derivatives containing the o-quinone group at the A or B ring and different substituents (alkyl groups, aryl groups or heterocycles) at the C ring of the compounds. The structure-activity relationships (SARs) were established based on the cytotoxicity data of compounds from the HL-60, Huh7, Hct116, and Hela cell lines. The cytotoxicity results showed that most compounds exhibited potent cytotoxicity. In particular, compound b-12 showed the best anti-proliferative activity (IC50 <= 1 mu M) against four cancer cell lines and strong potency against the HL-60/MX2 (0.47 mu M) cell line, which is resistant to Topo II poisons. Further studies showed that b-12 exhibited potent Topo II alpha inhibitory activity (IC50 = 7.54 mu M) compared with Topo I, which acted as a class of non-intercalative Topo IIa catalytic inhibitor by inhibiting the ATP binding site of Topo II. Cell apoptosis and cell cycle assays confirmed that b-12 could induce the apoptosis of Huh7 cells in a dose-dependent manner.

  DOI：

  10.1016/j.bioorg.2019.103131
• 作为产物：
  描述：

  1,8-二氨基萘 在 sodium metabisulfite 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 1-Methyl-2-ethylperimidin
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel perimidine o-quinone derivatives as non-intercalative topoisomerase II catalytic inhibitors

  摘要：

  For the development of novel anticancer agents, we designed and synthesized a total of 37 perimidine o-quinone derivatives containing the o-quinone group at the A or B ring and different substituents (alkyl groups, aryl groups or heterocycles) at the C ring of the compounds. The structure-activity relationships (SARs) were established based on the cytotoxicity data of compounds from the HL-60, Huh7, Hct116, and Hela cell lines. The cytotoxicity results showed that most compounds exhibited potent cytotoxicity. In particular, compound b-12 showed the best anti-proliferative activity (IC50 <= 1 mu M) against four cancer cell lines and strong potency against the HL-60/MX2 (0.47 mu M) cell line, which is resistant to Topo II poisons. Further studies showed that b-12 exhibited potent Topo II alpha inhibitory activity (IC50 = 7.54 mu M) compared with Topo I, which acted as a class of non-intercalative Topo IIa catalytic inhibitor by inhibiting the ATP binding site of Topo II. Cell apoptosis and cell cycle assays confirmed that b-12 could induce the apoptosis of Huh7 cells in a dose-dependent manner.

  DOI：

  10.1016/j.bioorg.2019.103131

文献信息

• ANISIMOVA V. A.; POZHARSKIJ A. F.; NIVOROZHKIN L. E.; MINKIN V. I., XIMIYA GETEROTSIKL. SOEDIN., 1978, HO 1,
  作者：ANISIMOVA V. A.、 POZHARSKIJ A. F.、 NIVOROZHKIN L. E.、 MINKIN V. I.

  DOI：——

  日期：——
• [EN] PPAR-SPARING COMPOUNDS FOR THE TREATMENT OF METABOLIC DISEASES<br/>[FR] COMPOSÉS ÉPARGNANT LES PPAR POUR LE TRAITEMENT DE MALADIES MÉTABOLIQUES
  申请人：METABOLIC SOLUTIONS DEV CO LLC

  公开号：WO2015013187A1

  公开（公告）日：2015-01-29

  The present invention relates to hydroxamate compounds and pharmaceutical compositions that are useful for treating and/or preventing metabolic inflammation mediated diseases such as diabetes, obesity, hypertension, dyslipidemia, a neurodegenerative disorder (e.g., Alzheimer's disease, Parkinson's disease, or Huntington's disease), or any combination thereof. Moreover, the present invention also provides methods of treatment for these diseases or disorders.