9,10-dihydro-N,5-dimethyl-9-oxo-4-acridinecarboxamide | 126479-84-3

• 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: 9,10-dihydro-N,5-dimethyl-9-oxo-4-acridinecarboxamide
• 英文别名: N,5-dimethyl-9-oxo-10H-acridine-4-carboxamide
• CAS: 126479-84-3
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: KTVCHWMBTJKPCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-N,5-dimethyl-9-oxo-4-acridinecarboxamide 在 氯化亚砜 作用下， 生成 4-methyl-9-chloroacridan-5-methylcarboxamide
  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
• 作为产物：
  描述：

  4-methyl-9-chloroacridan-5-methylcarboxamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以95%的产率得到9,10-dihydro-N,5-dimethyl-9-oxo-4-acridinecarboxamide
  参考文献：
  名称：

  抗癌氨基酸。双取代的氨苄青霉素类似物CI-921的工艺合成

  摘要：

  报道了一种改进的合成大量临床氨苄青霉素类似物CI-921的方法。还描述了该试剂的详细分析和光谱数据。

  DOI：

  10.1002/jhet.5570260542

文献信息

• Synthesis and Structure−Activity Relationships of Potential Anticancer Agents:  Alkylcarbamates of 3-(9-Acridinylamino)-5-hydroxymethylaniline
  作者：Tsann-Long Su、Ching-Huang Chen、Lin-Fei Huang、Chao-Hao Chen、Manas K. Basu、Xiu-Guo Zhang、Ting-Chao Chou

  DOI：10.1021/jm9901226

  日期：1999.11.1

  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.
• Anticancer anilinoacridines. A process synthesis of the disubstituted amsacrine analog CI-921
  作者：Sean T. Brennan、Norman L. Colbry、Robert L. Leeds、Boguslawa Leja、Stephen R. Priebe、Michael D. Reily、H. D. Hollis Showalter、Susan E. Uhlendorf、Graham J. Atwell、William A. Denny

  DOI：10.1002/jhet.5570260542

  日期：1989.9

  An improved process for the synthesis of bulk quantities of the clinical amsacrine analog CI-921 is reported. Described also are detailed analytical and spectroscopic data for this agent.

  报道了一种改进的合成大量临床氨苄青霉素类似物CI-921的方法。还描述了该试剂的详细分析和光谱数据。