3-methyl-4-((1-methyl-1H-indol-3-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-methyl-4-((1-methyl-1H-indol-3-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one
• 英文别名: 5-Methyl-4-[(1-methyl-3-indolyl)methylidene]-2-phenyl-3-pyrazolone；5-methyl-4-[(1-methylindol-3-yl)methylidene]-2-phenylpyrazol-3-one
• 化学式: C₂₀H₁₇N₃O
• 分子量: 315.374
• InChiKey: LDXSNVKQYCIAAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-[(二甲基氨基)亚甲基]-3-甲基-1-苯基-2-吡唑啉-5-酮 在 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 3-methyl-4-((1-methyl-1H-indol-3-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of indolylidinepyrazolones as potential anti-bacterial agents

  摘要：

  DOI：

  10.1016/j.tetlet.2014.05.131

文献信息

• Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy
  作者：Xia Zhou、Yuping Tan、Kun Gou、Lei Tao、Yuan Luo、Yue Zhou、Zeping Zuo、Qingxiang Sun、Youfu Luo、Yinglan Zhao

  DOI：10.1016/j.bioorg.2021.105159

  日期：2021.10

  adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest

  丝氨酸是从头合成嘌呤和脱氧胸苷所必需的一碳单元的来源，在癌细胞的生长中起着至关重要的作用。磷酸甘油酸脱氢酶 (PHGDH) 催化丝氨酸从头生物合成中的第一个限速步骤，已成为治疗癌症的有希望的靶点。在这里，我们从基于酶促测定的内部小分子库的筛选中确定了H-G6作为潜在的 PHGDH 抑制剂。我们采用了活性导向的组合化学合成策略来优化这种命中化合物。发现化合物b36是非竞争性和最有前途的化合物，其对 PHGDH 的IC 50值为 5.96 ± 0.61 μM。化合物b36抑制人乳腺癌和卵巢癌细胞的增殖，减少细胞内丝氨酸合成，破坏DNA合成，并诱导细胞周期停滞。总的来说，我们的结果表明b36是一种新型的 PHGDH 抑制剂，它可能是一种有前景的调节丝氨酸合成途径的调节剂，并且可能是一种潜在的抗癌先导物，值得进一步探索。
• The discovery of indole derivatives as novel hepatitis C virus inhibitors
  作者：Zhiqiang Han、Xiao Liang、Yaxin Wang、Jie Qing、Lin Cao、Luqing Shang、Zheng Yin

  DOI：10.1016/j.ejmech.2016.03.062

  日期：2016.6

  In this study, a library of in-house small molecule was screened using a HCV cell-based assay and a compound (1) containing an N-protected indole scaffold (NINS) was identified as a novel anti-HCV inhibitor. Through structure activity relationship (SAR) study, it was observed that the racemic inhibitor (10m) displayed good anti-HCV activity (EC50 = 1.02 +/- 0.10 mu M) with the excellent selectivity index (SI = 45.56). Interestingly, R-enantiomer ((R)-10m) showed better anti-HCV activity and lower cytotoxicity than S-enantiomer ((S)-10m). (R)-10m gave the best anti-HCV potency (EC50 = 0.72 +/- 0.09 mu M) with the highest selectivity index (SI > 69.44). In addition, the mechanism of action study of NINS derivatives demonstrated that NINS derivatives interfere with the early step (viral entry) of the HCV life cycle. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, and biological evaluation of indolylidinepyrazolones as potential anti-bacterial agents
  作者：A. Indrasena、Sd. Riyaz、Prema L. Mallipeddi、P. Padmaja、B. Sridhar、P.K. Dubey

  DOI：10.1016/j.tetlet.2014.05.131

  日期：2014.9