6-(三氟甲基)喹喔啉-2-甲醛 | 646512-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 6-(三氟甲基)喹喔啉-2-甲醛
• 英文名称: 6-trifluoromethylquinoxaline-2-carboxyaldehyde
• 英文别名: 6-(Trifluoromethyl)quinoxaline-2-carbaldehyde；6-(trifluoromethyl)quinoxaline-2-carbaldehyde
• CAS: 646512-64-3
• 化学式: C₁₀H₅F₃N₂O
• 分子量: 226.158
• InChiKey: KTPUBIYLEXXUSW-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  319.7±37.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-甲基-6-(三氟甲基)喹喔啉	2-methyl-6-trifluoromethylquinoxaline	646512-72-3	C10H7F3N2	212.174
  ——	2-Chloro-3-methyl-7-trifluoromethylquinoxaline	166402-14-8	C10H6ClF3N2	246.619

反应信息

• 作为反应物：
  描述：

  甲醇 、 diethyl N-(p-aminobenzoyl)-glutamate 、 6-(三氟甲基)喹喔啉-2-甲醛 反应 0.67h， 以60%的产率得到diethyl N-[4-(6-trifluoromethylquinoxalin-2-yl)methoxymethyl]aminobenzoyl-L-glutamate
  参考文献：
  名称：

  Quinoxaline chemistry. Part 15. 4-[2-Quinoxalylmethylenimino]-benzoylglutamates and -benzoates, 4-[2-quinoxalylmethyl-N-methylamino]-benzoylglutamates as analogues of classical antifolate agents. Synthesis, elucidation of structures and in vitro evaluation of antifolate and anticancer activities

  摘要：

  We report on an extension of our previous discovery of in vitro anticancer activity of trifluoromethylquinoxalines as analogues of classical and non-classical antifolic methotrexate and trimetrexate. In this case a small number of Schiff bases were obtained from the reaction of 2-bromethyl-3-R-6(7)trifluoromethylquinoxaline and ethyl p-aminobenzoylglutamate, ethyl p-aminobenzoate, p-toluidine instead of the expected 4-[2-quinoxalyl]methyl-N-methylanilino derivatives, which in turn formed with N-methylanilino derivatives. The reaction mechanism has been put forward. Structure elucidation of both Schiff bases and N-methylanilino analogues was achieved by a combination of 1H and 13C NMR spectra and hetcor experiments. Compounds 3a, 3b, 3c, 8, 11, 12, 13, Ie were tested in antifolic enzyme assay [Lactobacillus casei (LcTS), Leishmania major (LmTs), human Thymidylate synthase (hTs), human TS, human dihydrofolate reductase (hDHFR)] while compounds 3a, 3b, 3c were tested for anticancer activity. These results seem to indicate that the Schiff bases are somewhat active either as anticancer or as folate inhibitors, while compound Ie was selectively active against hDHFR with an inhibition constant (Ki) of 200 nM with a specificity of about 1000-folds with respect to hTS.

  DOI：

  10.1016/s0014-827x(02)00005-8
• 作为产物：
  描述：

  2-甲基-1,2,3,4-四氢-6-三氟甲基喹喔啉 在 盐酸 、 selenium(IV) oxide 、 水 、 双氧水 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 6.0h， 生成 6-(三氟甲基)喹喔啉-2-甲醛
  参考文献：
  名称：

  Quinoxaline chemistry. Part 15. 4-[2-Quinoxalylmethylenimino]-benzoylglutamates and -benzoates, 4-[2-quinoxalylmethyl-N-methylamino]-benzoylglutamates as analogues of classical antifolate agents. Synthesis, elucidation of structures and in vitro evaluation of antifolate and anticancer activities

  摘要：

  We report on an extension of our previous discovery of in vitro anticancer activity of trifluoromethylquinoxalines as analogues of classical and non-classical antifolic methotrexate and trimetrexate. In this case a small number of Schiff bases were obtained from the reaction of 2-bromethyl-3-R-6(7)trifluoromethylquinoxaline and ethyl p-aminobenzoylglutamate, ethyl p-aminobenzoate, p-toluidine instead of the expected 4-[2-quinoxalyl]methyl-N-methylanilino derivatives, which in turn formed with N-methylanilino derivatives. The reaction mechanism has been put forward. Structure elucidation of both Schiff bases and N-methylanilino analogues was achieved by a combination of 1H and 13C NMR spectra and hetcor experiments. Compounds 3a, 3b, 3c, 8, 11, 12, 13, Ie were tested in antifolic enzyme assay [Lactobacillus casei (LcTS), Leishmania major (LmTs), human Thymidylate synthase (hTs), human TS, human dihydrofolate reductase (hDHFR)] while compounds 3a, 3b, 3c were tested for anticancer activity. These results seem to indicate that the Schiff bases are somewhat active either as anticancer or as folate inhibitors, while compound Ie was selectively active against hDHFR with an inhibition constant (Ki) of 200 nM with a specificity of about 1000-folds with respect to hTS.

  DOI：

  10.1016/s0014-827x(02)00005-8