3,5-di-(trifluoromethyl)-N-[6-(3,5-di-(trifluoromethyl)benzoylamino)acridin-3-yl]benzamide | 1160799-59-6

• 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
• 英文名称: 3,5-di-(trifluoromethyl)-N-[6-(3,5-di-(trifluoromethyl)benzoylamino)acridin-3-yl]benzamide
• 英文别名: N-[6-[[3,5-bis(trifluoromethyl)benzoyl]amino]acridin-3-yl]-3,5-bis(trifluoromethyl)benzamide
• CAS: 1160799-59-6
• 化学式: C₃₁H₁₅F₁₂N₃O₂
• 分子量: 689.46
• InChiKey: QMPZPNZBMAIRSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  48
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  原黄素 、 3,5-双三氟甲基苯甲酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以47%的产率得到3,5-di-(trifluoromethyl)-N-[6-(3,5-di-(trifluoromethyl)benzoylamino)acridin-3-yl]benzamide
  参考文献：
  名称：

  Photo-inducible cytotoxic and clastogenic activities of 3,6-di-substituted acridines obtained by acylation of proflavine

  摘要：

  The cytotoxicity and photo-enhanced cytotoxicity of a series of 18 3,6-di-substituted acridines were evaluated on both tumour CHO cells and human normal keratinocytes, and compared to their corresponding clastogenicity as assessed by the micronucleus assay.Compounds 2f tert-butyl N-[(6-tert-butoxycarbonylamino)acridin-3-yl]carbamate and 2d N-[6-(pivalamino)acridin-3-yl]pivalamide displayed a specific cytotoxicity on CHO cells. These results suggested that the two derivatives could be considered as interesting candidates for anticancer chemotherapy and hypothesized that the presence of 1,1-dimethylethyl substituents was responsible for a strong non-clastogenic cytotoxicity. Compounds 2b and 2c, on the contrary, displayed a strong clastogenicity. They indicated that the presence of nonbranched aliphatic chains on positions 3 and 6 of the acridine rings tended to induce a significant clastogenic effect. Finally, they established that most of the acridine compounds could be photo-activated by UVA-visible rays and focussed on the significant role of light irradiation on their biological properties. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.010

文献信息

• Photo-inducible cytotoxic and clastogenic activities of 3,6-di-substituted acridines obtained by acylation of proflavine
  作者：Yohann Benchabane、Carole Di Giorgio、Gérard Boyer、Anne-Sophie Sabatier、Diane Allegro、Vincent Peyrot、Michel De Méo

  DOI：10.1016/j.ejmech.2009.01.010

  日期：2009.6

  The cytotoxicity and photo-enhanced cytotoxicity of a series of 18 3,6-di-substituted acridines were evaluated on both tumour CHO cells and human normal keratinocytes, and compared to their corresponding clastogenicity as assessed by the micronucleus assay.Compounds 2f tert-butyl N-[(6-tert-butoxycarbonylamino)acridin-3-yl]carbamate and 2d N-[6-(pivalamino)acridin-3-yl]pivalamide displayed a specific cytotoxicity on CHO cells. These results suggested that the two derivatives could be considered as interesting candidates for anticancer chemotherapy and hypothesized that the presence of 1,1-dimethylethyl substituents was responsible for a strong non-clastogenic cytotoxicity. Compounds 2b and 2c, on the contrary, displayed a strong clastogenicity. They indicated that the presence of nonbranched aliphatic chains on positions 3 and 6 of the acridine rings tended to induce a significant clastogenic effect. Finally, they established that most of the acridine compounds could be photo-activated by UVA-visible rays and focussed on the significant role of light irradiation on their biological properties. (C) 2009 Elsevier Masson SAS. All rights reserved.