10-(5-bromopentyl)acridin-9(10H)-one

• 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: 10-(5-bromopentyl)acridin-9(10H)-one
• 英文别名: 10-(5'-N-bromopentyl)acridone；10-(5-bromopentyl)acridin-9-one
• 化学式: C₁₈H₁₈BrNO
• 分子量: 344.251
• InChiKey: KPZNQTVTRWWMTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-(5-bromopentyl)acridin-9(10H)-one 在 哌啶 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.5h， 生成 5-(((1-5-(9-oxoacridin-10(9H)-yl)pentyl)-1H-pyrrol-2-yl)methylene)pyrimidine-2,4,6 (1H,3H,5H)-trione
  参考文献：
  名称：

  Targeting tyrosine kinase: Development of acridone – pyrrole – oxindole hybrids against human breast cancer

  摘要：

  Based on the molecular modelling studies, a rational modification of the lead molecule was made to develop highly potent compounds showing anti-cancer activity against human breast cancer cell lines MCF 7, MDA-MB-468 and T-47D. The most potent compounds have Log P and total polar surface area 4.4-5.4 and 59.8 angstrom, respectively and they also exhibited promising ADME profile.

  DOI：

  10.1016/j.bmcl.2018.11.021
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 硫酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 10-(5-bromopentyl)acridin-9(10H)-one
  参考文献：
  名称：

  Targeting tyrosine kinase: Development of acridone – pyrrole – oxindole hybrids against human breast cancer

  摘要：

  Based on the molecular modelling studies, a rational modification of the lead molecule was made to develop highly potent compounds showing anti-cancer activity against human breast cancer cell lines MCF 7, MDA-MB-468 and T-47D. The most potent compounds have Log P and total polar surface area 4.4-5.4 and 59.8 angstrom, respectively and they also exhibited promising ADME profile.

  DOI：

  10.1016/j.bmcl.2018.11.021

文献信息

• Synthesis, cytotoxicity evaluation, and molecular modeling studies of 2,<i>N</i>¹⁰-substituted acridones as DNA-intercalating agents
  作者：Nisachon Khunnawutmanotham、Watthanachai Jumpathong、Chatchakorn Eurtivong、Nitirat Chimnoi、Supanna Techasakul

  DOI：10.1177/1747519820902674

  日期：2020.7

  Acridine-based compounds possess anticancer activities by intercalating to DNA. Although they have chemotherapeutic potential, acridine-based compounds are not used to treat cancer. In this study, 2,N10-acridone derivatives are designed and synthesized based on acridone, a ketone derivative of acridine. Herein, acridone is functionalized with alkyl side chains containing terminal nitrogen-based moieties

  吖啶类化合物通过嵌入 DNA 具有抗癌活性。尽管它们具有化学治疗潜力，但基于吖啶的化合物不用于治疗癌症。本研究以吖啶酮衍生物吖啶酮为基础，设计合成了2,N10-吖啶酮衍生物。在本文中，吖啶酮被烷基侧链官能化，该侧链在 N10 位含有末端氮基部分并在 C2 位被取代。评估产品对四种癌细胞系的体外细胞毒性：Molt-3、HepG2、A549 和 HuCCA-1。在 C2 和 N10 位带有两个丁基哌啶侧链的衍生物是最活跃的，IC50 值范围为 2.96 到 9.46 µM。分子建模研究支持衍生物通过嵌入与 DNA 结合，
• Targeting tyrosine kinase: Development of acridone – pyrrole – oxindole hybrids against human breast cancer
  作者：Manpreet Kaur、Palwinder Singh

  DOI：10.1016/j.bmcl.2018.11.021

  日期：2019.1

  Based on the molecular modelling studies, a rational modification of the lead molecule was made to develop highly potent compounds showing anti-cancer activity against human breast cancer cell lines MCF 7, MDA-MB-468 and T-47D. The most potent compounds have Log P and total polar surface area 4.4-5.4 and 59.8 angstrom, respectively and they also exhibited promising ADME profile.