2-bromo-1-(10H-phenothiazin-10-yl)butan-1-one | 4063-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2-bromo-1-(10H-phenothiazin-10-yl)butan-1-one
• 英文别名: 2-bromo-1-phenothiazin-10-ylbutan-1-one
• CAS: 4063-35-8
• 化学式: C₁₆H₁₄BrNOS
• 分子量: 348.263
• InChiKey: WLHMVAPEBICIOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(10H-phenothiazin-10-yl)butan-1-one 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 ethyl 2-(3-((1-oxo-1-(10H-phenothiazin-10-yl)butan-2-yl)thio)-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetate
  参考文献：
  名称：

  Inauhzin analogues that induce P53, inhibit cell growth, and have antitumor activity

  摘要：

  Inauhzin (INZ)被鉴定为一种新型的p53激活剂，可以选择性和高效地抑制肿瘤生长，而不显示基因毒性，并且对正常细胞的毒性很小。一系列INZ类似物被合成并评估其在细胞基础实验中诱导细胞p53和抑制细胞生长的能力。正如所描述的，这导致了INZ类似物37的发现，这种分子在多种人类癌细胞系中，包括H460和HCT116+/+细胞中，p53激活和细胞生长抑制方面的效力比INZ要好得多。这种INZ类似物对p53-null H1299细胞的影响要小得多，而且对正常人类含有p53的WI-38细胞没有毒性。这些结果还揭示了INZ活性的关键化学特征，并确定了新合成的INZ类似物37作为进一步开发抗癌治疗的更好的小分子。

  公开号：

  US09447103B2

文献信息

• INAUHZIN ANALOGUES THAT INDUCE P53, INHIBIT CELL GROWTH, AND HAVE ANTITUMOR ACTIVITY
  申请人：Indiana University Research and Technology Corp.

  公开号：US20150197522A1

  公开（公告）日：2015-07-16

  Inauhzin (INZ) was identified as a novel p53 activator, which selectively and efficiently suppressing tumor growth without displaying genotoxicity and with little toxicity to normal cells. A panel of INZ analogs were synthesized and evaluated their ability to induce cellular p53 and to inhibit cell growth in cell-based assays. As described, this leads to the discovery of INZ analog 37, a molecule that exhibits much better potency than INZ in both of p53 activation and cell growth inhibition in several human cancer cell lines including H460 and HCT116 +/+ cells. This INZ analog exhibited a much lower effect on p53-null H1299 cells and importantly no toxicity towards normal human p53-containing WI-38 cells. Those results also reveal key chemical features for INZ activity, and identify the newly synthesized INZ analog 37 as a better small molecule for further development of anti-cancer therapies.

  Inauhzin（INZ）被确定为一种新型p53激活剂，它能够选择性、高效地抑制肿瘤生长，而不显示遗传毒性，并对正常细胞毒性较小。一系列INZ类似物被合成并评估了它们诱导细胞p53和抑制细胞生长的能力。正如所述，这导致了INZ类似物37的发现，这种分子在多种人类癌细胞系中，包括H460和HCT116 +/+细胞系中，p53激活和细胞生长抑制方面的效力比INZ更强。这种INZ类似物对p53-null H1299细胞的影响要小得多，而且对正常人类p53含有的WI-38细胞没有毒性。这些结果还揭示了INZ活性的关键化学特征，并确定了新合成的INZ类似物37作为进一步开发抗癌疗法的更好的小分子。
• US9447103B2
  申请人：——

  公开号：US9447103B2

  公开（公告）日：2016-09-20
• [EN] INAUHZIN ANALOGUES THAT INDUCE P53, INHIBIT CELL GROWTH, AND HAVE ANTITUMOR ACTIVITY<br/>[FR] ANALOGUES DE L'INAUHZINE INDUISANT P53, INHIBANT LA CROISSANCE CELLULAIRE ET POSSÉDANT UNE ACTIVITÉ ANTITUMORALE
  申请人：INDIANA UNIVERSITY RESARCH AND TECHNOLOGY CORP

  公开号：WO2014018953A1

  公开（公告）日：2014-01-30

  Inauhzin (INZ) was identified as a novel p53 activator, which selectively and efficiently suppressing tumor growth without displaying genotoxicity and with little toxicity to normal cells. A panel of INZ analogs were synthesized and evaluated their ability to induce cellular p53 and to inhibit cell growth in cell-based assays. As described, this leads to the discovery of INZ analog 37, a molecule that exhibits much better potency than INZ in both of p53 activation and cell growth inhibition in several human cancer cell lines including H460 and HCT116+/+ cells. This INZ analog exhibited a much lower effect on p53-null H1299 cells and importantly no toxicity towards normal human p53 -containing WI-38 cells. Those results also reveal key chemical features for INZ activity, and identify the newly synthesized INZ analog 37 as a better small molecule for further development of anti-cancer therapies.
• Inauhzin analogues that induce P53, inhibit cell growth, and have antitumor activity
  申请人：Indiana University Research and Technology Corp.

  公开号：US09447103B2

  公开（公告）日：2016-09-20

  Inauhzin (INZ) was identified as a novel p53 activator, which selectively and efficiently suppressing tumor growth without displaying genotoxicity and with little toxicity to normal cells. A panel of INZ analogs were synthesized and evaluated their ability to induce cellular p53 and to inhibit cell growth in cell-based assays. As described, this leads to the discovery of INZ analog 37, a molecule that exhibits much better potency than INZ in both of p53 activation and cell growth inhibition in several human cancer cell lines including H460 and HCT116+/+ cells. This INZ analog exhibited a much lower effect on p53-null H1299 cells and importantly no toxicity towards normal human p53-containing WI-38 cells. Those results also reveal key chemical features for INZ activity, and identify the newly synthesized INZ analog 37 as a better small molecule for further development of anti-cancer therapies.

  Inauhzin (INZ)被鉴定为一种新型的p53激活剂，可以选择性和高效地抑制肿瘤生长，而不显示基因毒性，并且对正常细胞的毒性很小。一系列INZ类似物被合成并评估其在细胞基础实验中诱导细胞p53和抑制细胞生长的能力。正如所描述的，这导致了INZ类似物37的发现，这种分子在多种人类癌细胞系中，包括H460和HCT116+/+细胞中，p53激活和细胞生长抑制方面的效力比INZ要好得多。这种INZ类似物对p53-null H1299细胞的影响要小得多，而且对正常人类含有p53的WI-38细胞没有毒性。这些结果还揭示了INZ活性的关键化学特征，并确定了新合成的INZ类似物37作为进一步开发抗癌治疗的更好的小分子。