(4Z)-4-((dimethylamino)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one | 65644-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (4Z)-4-((dimethylamino)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
• 英文别名: (Z)-4-((dimethylamino)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one；4-dimethylaminomethylene-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one；(4Z)-4-[(dimethylamino)methylidene]-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one；(4Z)-4-(dimethylaminomethylidene)-5-methyl-2-phenylpyrazol-3-one
• CAS: 65644-13-5
• 化学式: C₁₃H₁₅N₃O
• 分子量: 229.282
• InChiKey: ZKMQJGARZNSQNV-XFXZXTDPSA-N

物化性质

• 沸点：
  309.1±52.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Fluoro-4-{[6-methoxy-7-(3-morpholinopropoxy)-4-quinolyl]oxy}-aniline 、 (4Z)-4-((dimethylamino)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one 在 溶剂黄146 作用下， 以72%的产率得到(4Z)-4-(((3-fluoro-4-((6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yl)oxy)phenyl)amino)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents

  摘要：

  Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant cytotoxicity and high selectivity against HT-29, H460 and A549 cancer cell lines as compared with foretinib. The SAR analyses indicated that compounds with halogen groups, especially trifluoromethyl groups at 2-position on the phenyl ring (moiety B) were more effective. In this study, a promising compound 17 (c-Met IC50 = 2.20 nM, a multi-target tyrosine kinase inhibitor) showed the most potent antitumor activities with IC50 values of 0.14 mu M, 0.18 mu M, 0.09 mu M, 0.03 mu M, and 1.06 mu M against HT-29, H460, A549, MKN-45, and U87MG cell lines, respectively. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.07.011
• 作为产物：
  描述：

  苯胺 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 5.5h， 生成 (4Z)-4-((dimethylamino)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents

  摘要：

  Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant cytotoxicity and high selectivity against HT-29, H460 and A549 cancer cell lines as compared with foretinib. The SAR analyses indicated that compounds with halogen groups, especially trifluoromethyl groups at 2-position on the phenyl ring (moiety B) were more effective. In this study, a promising compound 17 (c-Met IC50 = 2.20 nM, a multi-target tyrosine kinase inhibitor) showed the most potent antitumor activities with IC50 values of 0.14 mu M, 0.18 mu M, 0.09 mu M, 0.03 mu M, and 1.06 mu M against HT-29, H460, A549, MKN-45, and U87MG cell lines, respectively. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.07.011

文献信息

• SMIRNOVA, N. P.;KVITKO, I. YA.;ELTSOV, A. V., ZH. ORGAN. XIMII, 1986, 22, N 3, 650-660
  作者：SMIRNOVA, N. P.、KVITKO, I. YA.、ELTSOV, A. V.

  DOI：——

  日期：——
• TOKMAKOV G. P.; ZEMLYANOVA T. G.; GRANDBERG I. I., IZV. TIMIRYAZEV. S.-X. AKAD.,(1986) N 5, 166-169
  作者：TOKMAKOV G. P.、 ZEMLYANOVA T. G.、 GRANDBERG I. I.

  DOI：——

  日期：——
• WRZECIONO U.; SZOSTAK-RZEPIAK B., PHARMAZIE <PHAR-AT>, 1975, 30, NO 9, 582-585
  作者：WRZECIONO U.、 SZOSTAK-RZEPIAK B.

  DOI：——

  日期：——
• Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents
  作者：Shunguang Zhou、Jianguo Ren、Mingmei Liu、Lixiang Ren、Yajing Liu、Ping Gong

  DOI：10.1016/j.bioorg.2014.07.011

  日期：2014.12

  Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant cytotoxicity and high selectivity against HT-29, H460 and A549 cancer cell lines as compared with foretinib. The SAR analyses indicated that compounds with halogen groups, especially trifluoromethyl groups at 2-position on the phenyl ring (moiety B) were more effective. In this study, a promising compound 17 (c-Met IC50 = 2.20 nM, a multi-target tyrosine kinase inhibitor) showed the most potent antitumor activities with IC50 values of 0.14 mu M, 0.18 mu M, 0.09 mu M, 0.03 mu M, and 1.06 mu M against HT-29, H460, A549, MKN-45, and U87MG cell lines, respectively. (C) 2014 Elsevier Inc. All rights reserved.