4-nitro-9-chloroacridine | 6237-21-4

• 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: 4-nitro-9-chloroacridine
• 英文别名: 9-chloro-4-nitro-acridine；9-Chlor-4-nitro-acridin；5-Nitro-9-chloroacridine；9-chloro-4-nitroacridine
• CAS: 6237-21-4
• 化学式: C₁₃H₇ClN₂O₂
• 分子量: 258.664
• InChiKey: LLNSUQJKNJFFCH-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C
• 沸点：
  453.8±20.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-nitro-9-chloroacridine 在 ammonium carbonate 、 苯酚 作用下， 生成 4-nitro-9-aminoacridine
  参考文献：
  名称：

  Albert; Gledhill, Journal of the Society of Chemical Industry, 1949, vol. 64, p. 169,171

  摘要：

  DOI：
• 作为产物：
  描述：

  4-nitro-9(10H)-acridinone 在 氯化亚砜 作用下， 生成 4-nitro-9-chloroacridine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Potential Anticancer Agents:  Alkylcarbamates of 3-(9-Acridinylamino)-5-hydroxymethylaniline

  摘要：

  A series of potential 9-anilinoacridine antitumor agents, 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA) derivatives with monosubstituent at C4' and disubstituents at C4' and C5' of the acridine ring and their alkylcarbamates, were synthesized for evaluation of their antitumor activity. A structure-activity relationship (SAR) study showed that the AHMA-alkylcarbamates were more potent than their corresponding parent AHMA compounds. In addition, the cytotoxicity of the AHMA-alkylcarbamate decreased with increasing length and size of the alkyl function. Among these compounds, AHMA-ethylcarbamate (18) and 4'-methyl-5'-dimethylaminoethylcarboxamido-AHMA-ethylcarbamate (34) possess potent cytotoxicity on the inhibition of human leukemic HL-60 cell growth in culture. Further in vivo studies of these compounds displayed significant anticancer therapeutic effects in mice bearing sarcoma 180, Lewis lung carcinoma, and P388 leukemia.

  DOI：

  10.1021/jm9901226

文献信息

• NEUROLOGICALLY ACTIVE COMPOUNDS
  申请人：Barnham Kevin Jeffrey

  公开号：US20100160346A1

  公开（公告）日：2010-06-24

  The present invention relates to neurologically-active compounds, processes for their preparation and their use as pharmaceutical or veterinary agents, in particular for the treatment of neurological conditions, more specifically neurodegenerative conditions such as Alzheimer's disease.

  本发明涉及神经活性化合物，其制备方法以及它们作为制药或兽医制剂的用途，特别是用于治疗神经系统疾病，更具体地说是神经退行性疾病，如阿尔茨海默病。
• 213. Nitration products of 5-aminoacridine, and the synthesis of 1 : 5- and 4 : 5-diaminoacridine
  作者：A. Hampton、D. Magrath

  DOI：10.1039/jr9490001008

  日期：——
• NOVEL FLUORESCENT DYES AND USES THEREOF
  申请人：Almac Sciences (Scotland) Limited

  公开号：EP1940965B1

  公开（公告）日：2014-03-26
• Kunikowski, Antoni; Ledochowski, Andrzej, Polish Journal of Chemistry, 1983, vol. 57, # 4/5/6, p. 435 - 445
  作者：Kunikowski, Antoni、Ledochowski, Andrzej

  DOI：——

  日期：——
• Albert; Gledhill, Journal of the Society of Chemical Industry, 1945, vol. 64, p. 169,170
  作者：Albert、Gledhill

  DOI：——

  日期：——