喹喔啉,3-甲基-2-苯基-6-(三氟甲基)- | 102729-43-1

• 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: 喹喔啉,3-甲基-2-苯基-6-(三氟甲基)-
• 英文名称: 3-Phenyl-7-trifluoromethyl-2-methylquinoxaline
• 英文别名: 3-methyl-2-phenyl-6-trifluoromethylquinoxaline；3-Methyl-2-phenyl-6-(trifluoromethyl)quinoxaline
• CAS: 102729-43-1
• 化学式: C₁₆H₁₁F₃N₂
• 分子量: 288.272
• InChiKey: SGANBUYZDGLOFH-UHFFFAOYSA-N

物化性质

• 沸点：
  356.4±37.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  喹喔啉,3-甲基-2-苯基-6-(三氟甲基)- 在 selenium(IV) oxide 作用下， 以 乙酸乙酯 为溶剂， 125.0~130.0 ℃ 、93.33 Pa 条件下， 反应 18.0h， 生成 diethyl N-[4-(3-phenyl-7-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：

  3-phenyl-7-trifluoromethylquinoxalin-2(1H)-one 在 palladium on activated charcoal 盐酸 、 氢气 、 双氧水 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 18.0~25.0 ℃ 、303.98 kPa 条件下， 反应 28.0h， 生成 喹喔啉,3-甲基-2-苯基-6-(三氟甲基)-
  参考文献：
  名称：

  Loriga, Mario; Paglietti, Giuseppe, Journal of Chemical Research, Miniprint, 1986, # 1, p. 277 - 296

  摘要：

  DOI：

文献信息

• Quinoxaline chemistry. Part 11. 3-Phenyl-2 [phenoxy- and phenoxymethyl]-6(7) or 6,8-substituted quinoxalines and N-[4-(6(7)-substituted or 6,8-disubstituted-3-phenylquinoxalin-2-yl)hydroxy or hydroxymethyl]benzoylglutamates. Synthesis and evaluation of in vitro anticancer activity and enzymatic inhibitory activity against dihydrofolate reductase and thymidylate synthase
  作者：Paola Corona、Gabriella Vitale、Mario Loriga、Giuseppe Paglietti、Maria Paola Costi

  DOI：10.1016/s0014-827x(98)00054-8

  日期：1998.7

  Twenty-four out of twenty-nine quinoxalines were selected at the National Cancer Institute, Bethesda, Md, USA, for in vitro anticancer screening. Among these, 10 derivatives exhibited high values of percent tumor growth inhibition at a concentration of 10(-4) M in all cancer cell lines. Four of these compounds maintained these values at 10(-5) M, whereas a certain number exhibited significant values of percent inhibition at the most diluted concentrations (10(-8)-10(-6) M). Inhibitory activity against dihydrofolate reductase (DHFR) (bovine and rat liver) was determined for the most active compounds. This test showed that this type of quinoxaline exhibited an appreciable activity in comparison with the previously described aza analogues. In the other test (Lactobacillus casei, thymidylate synthase (TS), human HTS) no or poor activity was detected in both series of compounds. (C) 1998 Elsevier Science S.A. All rights reserved.
• 2-Phenyl-6(7)-R-substituted quinoxalines N-oxides. Synthesis, structure elucidation and antimicrobial activity
  作者：M Loriga、A Nuvole、G Paglietti、G Fadda、S Zanetti

  DOI：10.1016/0223-5234(90)90147-u

  日期：1990.7
• LORIGA, M.;PAGLIETTI, G., J. CHEM. RES. SYNOP., 1986, N 1, 16-17
  作者：LORIGA, M.、PAGLIETTI, G.

  DOI：——

  日期：——