4-肼基-1-甲基-2(1H)-喹啉酮 | 192633-21-9

• 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
• 中文名称: 4-肼基-1-甲基-2(1H)-喹啉酮
• 英文名称: 4-hydrazino-1-methyl-2(1H)-quinolinone
• 英文别名: 4-Hydrazino-1-methylquinolin-2(1H)-one；4-hydrazinyl-1-methylquinolin-2-one
• CAS: 192633-21-9
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: ZYSGUISDGDUDLK-UHFFFAOYSA-N

物化性质

• 沸点：
  355.8±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 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：
  58.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-肼基-1-甲基-2(1H)-喹啉酮 在 盐酸 、 sodium nitrite 作用下， 以76%的产率得到4-叠氮基-1-甲基喹啉-2-酮
  参考文献：
  名称：

  取代喹啉酮的化学。第二部分新型4-吡唑喹啉酮衍生物的合成

  摘要：

  摘要 4-Hydrazino-1-methyl-2(1H)quinolinone (2) 用氯酞嗪、亚硝酸、异硫氰酸盐和靛红处理，并用作一些新的4-吡唑基喹啉酮的前体。2与某些3-酰基喹啉酮反应得到喹啉基吡唑并喹啉酮和/或喹啉基吡唑基喹啉酮。

  DOI：

  10.1080/00397910008086898
• 作为产物：
  描述：

  4-氯-1-甲基-1H-喹啉-2-酮 在 一水合肼 作用下， 反应 12.0h， 生成 4-肼基-1-甲基-2(1H)-喹啉酮
  参考文献：
  名称：

  4-Hydrazinylquinolin-2(1H)-one 的自氧化；哒嗪酮[4,3-c:5,6-c′]diquinoline-6,7(5H,8H)-二酮的合成

  摘要：

  通过 4-hydrazinylquinolin-2( 1H ) -ones 的自氧化，实现了一系列哒嗪并[4,3- c : 5,6- c ']二喹啉的有效合成。IR、NMR（1 H 和13 C）、质谱数据和元素分析用于拟合和阐明新合成化合物的结构。X射线结构分析和理论计算明确地证明了结构的形成。还讨论了该反应的可能机理。

  DOI：

  10.3390/molecules27072125

文献信息

• CHEMISTRY OF SUBSTITUTED QUINOLINONES. III. SYNTHESIS AND REACTIONS OF SOME NOVEL 3-PYRAZOLYL-2-QUINOLINONES
  作者：Mohamed Abass、Elham S. Othman

  DOI：10.1081/scc-100106047

  日期：2001.1

  The preparation of 4-hydroxy-1-methyl-3-(5-oxo-4,5-dihydro-1H-3-pyrazolyl)-1,2-dihydro-2-quinolinone (3) and its hydrazono-, aminomethylidene- and arylidene derivatives has been achieved. The synthesis of fused heterocyclic polynuclear systems containing quinolinone moiety is also described.

  4-羟基-1-甲基-3-(5-oxo-4,5-dihydro-1H-3-pyrazolyl)-1,2-dihydro-2-quinolinone(3)及其腙、氨基亚甲基-的制备和亚芳基衍生物已经实现。还描述了含有喹啉酮部分的稠合杂环多核系统的合成。
• New quinoline-2-one/pyrazole derivatives; design, synthesis, molecular docking, anti-apoptotic evaluation, and caspase-3 inhibition assay
  作者：Ashraf A. Aly、Samia M. Sayed、El-Shimaa M.N. Abdelhafez、Sara Mohamed Naguib Abdelhafez、Walaa Yehia Abdelzaher、Mohamed A. Raslan、Amira E. Ahmed、Khaled Thabet、Ahmed A.M. El-Reedy、Alan B. Brown、Stefan Bräse

  DOI：10.1016/j.bioorg.2019.103348

  日期：2020.1

  cells while compound 6e showed dilated blood vessels with more apoptotic cells if compared with NAC. Caspase-3 inhibition assay revealed that compounds 6a, 6b and 6d weaken caspase-3 expression to an extent higher than NAC (1.063, 0.430, 0.731 and 1.115, respectively). Docking studies with caspase-3 revealed that most of the tested compounds showed good binding with the enzyme especially for compound

  我们报告了新的喹啉-2-一/吡唑杂化物的合成及其抗凋亡活性。使用N-乙酰半胱氨酸（NAC）作为抗凋亡参考，研究了减少I / R诱导的大鼠结肠组织损伤的效果。与模型组相比，化合物6a，6c和6f的氧化应激参数MDA，SOD，GSH和NOx表现出显着改善，并且比参考NAC（N-乙酰半胱氨酸）更大，而化合物6d和6e与模型组相比显示出较弱的抗氧化活性。参考NAC。此外，与模型组相比，化合物6a，6c和6f显示出炎性介质TNFα和CRB的降低显着大于NAC，尤其是化合物6c，其与conc 2.13mg / dL的NAC相比发现CRB为1.90（mg / dL）。此外，对所有目标化合物进行了结肠组织病理学研究，结果表明，与NAC相比，化合物6a和6f的H＆E切片显示明显的正常结肠细胞，而化合物6e显示的血管扩张，凋亡细胞更多。Caspase-3抑制分析表明，化合物6a，6b和6d减弱caspase-3的表达的程度高于NAC（分别为1
• Chemistry of Substituted Quinolinones. Part 8. Synthesis and Cyclization Reactions of Ethyl 5-Amino-1-(1-methyl-2-oxoquinolin-4-YL)-3-methylsulfanylpyrazole-4-carboxylate
  作者：Mohamed Abass

  DOI：10.1080/10426500307880

  日期：2003.7

  led to the acid 5 and acetamide 7 , which were cyclized to the pyrazolopyridones 6 and 8 , respectively. Condensation of 3 with 2,5-dimethoxytetrahydrofuran afforded the pyrrolylpyrazole 9 , which underwent cyclization by action of PPA to give pyrazolopyrrolizine 10 . Treating 3 with thiophosgene gave the pyrazolyl isothiocyanate 11 , which added aniline to yield the thiourea derivative 12 , and cyclized

  描述了标题氨基酯 3 的合成，其水解和氯乙酰化产生酸 5 和乙酰胺 7，它们分别环化为吡唑并吡啶酮 6 和 8。3 与 2,5-二甲氧基四氢呋喃缩合得到吡咯基吡唑 9 ，其在 PPA 的作用下进行环化得到吡唑并吡咯嗪 10 。用硫光气处理3得到吡唑基异硫氰酸酯11，其加入苯胺得到硫脲衍生物12，并环化得到吡唑并嘧啶硫酮13-15。3 与甲酰胺缩合得到吡唑并嘧啶 16，而与原甲酸三乙酯缩合生成乙氧基亚甲基氨基吡唑 18，其与肼缩合得到氨基吡唑并嘧啶 19。3 与劳森试剂的反应产生吡唑并噻唑膦 21 。
• Novel Pyrazoloquinolin-2-ones: Design, synthesis, docking studies, and biological evaluation as antiproliferative EGFR-TK inhibitors
  作者：Mohammed A.I. Elbastawesy、Ashraf A. Aly、Mohamed Ramadan、Yaseen A.M.M. Elshaier、Bahaa G.M. Youssif、Alan B. Brown、Gamal El-Din A Abuo-Rahma

  DOI：10.1016/j.bioorg.2019.103045

  日期：2019.9

  Two new series of diethyl 2-[2-(substituted-2-oxo-1,2-dihydroquinolin-4-yl)hydrazono]-succinates 6a-g and 1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazoles 7a-f have been designed and synthesized. The structures of the synthesized compounds were proved by IR, mass, NMR (2D) spectra and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, seven compounds were further examined against the most sensitive cell lines, leukemia CCRFCEM, and MOLT-4. 5-Amino-1-(6-bromo-2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazole-3,4-dicarbonitrile (7f) was the most active product, with IC50= 1.35 uM and 2.42 uM against MOLT-4 and CCRF-CEM, respectively. Also, it showed a remarkable inhibitory activity compared to erlotinib on the EGFR TK with IC50 = 247.14 nM and 208.42 nM, respectively. Cell cycle analysis of MOLT-4 cells treated with 7f showed cell cycle arrest at G2/M phase (supported by Caspases, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking study indicated that both the pyrazole moiety and the quinolin-2-one ring showed good fitting into EGFR (PDB code: 1M17). In order to interpret SAR of the designed compounds, and provide a basis for further optimization, molecular docking of the synthesized compounds to known EGFR inhibitors was performed. The study illustrated the effect of several factors on the compounds' activity.
• Chemistry of Substituted Quinolinones. Part II Synthesis of Novel 4-Pyrazolylquinolinone Derivatives
  作者：Mohamed Abass

  DOI：10.1080/00397910008086898

  日期：2000.8

  Abstract 4-Hydrazino-1-methyl-2(1H)quinolinone (2) was treated with chlorophthalazine, nitrous acid, isothiocyanates and isatines, and also utilized as' a precursor for some new 4-pyrazolylquinolinones. Reaction of 2 with certain 3-acylquinolinones afforded quinolinylpyrazoloquinolinones and/or quinolinylpyrazolylquinolinones.

  摘要 4-Hydrazino-1-methyl-2(1H)quinolinone (2) 用氯酞嗪、亚硝酸、异硫氰酸盐和靛红处理，并用作一些新的4-吡唑基喹啉酮的前体。2与某些3-酰基喹啉酮反应得到喹啉基吡唑并喹啉酮和/或喹啉基吡唑基喹啉酮。