5-(9-acridinylamino)-p-toluidine | 80267-00-1

• 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: 5-(9-acridinylamino)-p-toluidine
• 英文别名: 3-N-acridin-9-yl-4-methylbenzene-1,3-diamine;hydrochloride
• CAS: 80267-00-1
• 化学式: C₂₀H₁₇N₃*2ClH
• 分子量: 372.297
• InChiKey: PQTUMZSWYLQHJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  50.9
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 5-(9-acridinylamino)-p-toluidine 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以64%的产率得到
  参考文献：
  名称：

  New analogues of AHMA as potential antitumor agents: synthesis and biological activity

  摘要：

  A series of new analogues of 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA, 1) and AHMA-ethylcarbamate (2) were synthesized by introducing an O-alkylcarboxylic acid esters to the CH2OH function, displacing the CH2OH function with a dimethylaminocarboxamido group or with a methyl function introduced at the meta-, para- or ortho-position to the NH2 group to form 5-(9-acridinylamino)-m-toluidines (AMTs), 5-(9-acridinylamino)-p-toluidines (APTs) or 5-(9-acridinylamino)-o-toluidines (AOTs), respectively. The inhibitions of a variety of human tumor cell growth, interactions with DNA as well as inhibitory effect against topoisomerase 11 (Topo 11) of these new agents were studied. Among AMT, APT and AOT derivatives with dimethylaminoethylcarboxamido and Me at C4 and C5 of acridine moiety (i.e., 21c, 23c and 26c) were more cytotoxic than AHMA (1) and AHMA-ethylcarbamate (2), depending upon the tumor cell line tested. Detailed structure-activity relationships of the new analogues were studied. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.001
• 作为产物：
  描述：

  9-氯吖啶 、 2,4-二氨基甲苯 在 N-甲基吗啉 作用下， 以 乙醇 、 氯仿 为溶剂， 以86%的产率得到5-(9-acridinylamino)-p-toluidine
  参考文献：
  名称：

  New analogues of AHMA as potential antitumor agents: synthesis and biological activity

  摘要：

  A series of new analogues of 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA, 1) and AHMA-ethylcarbamate (2) were synthesized by introducing an O-alkylcarboxylic acid esters to the CH2OH function, displacing the CH2OH function with a dimethylaminocarboxamido group or with a methyl function introduced at the meta-, para- or ortho-position to the NH2 group to form 5-(9-acridinylamino)-m-toluidines (AMTs), 5-(9-acridinylamino)-p-toluidines (APTs) or 5-(9-acridinylamino)-o-toluidines (AOTs), respectively. The inhibitions of a variety of human tumor cell growth, interactions with DNA as well as inhibitory effect against topoisomerase 11 (Topo 11) of these new agents were studied. Among AMT, APT and AOT derivatives with dimethylaminoethylcarboxamido and Me at C4 and C5 of acridine moiety (i.e., 21c, 23c and 26c) were more cytotoxic than AHMA (1) and AHMA-ethylcarbamate (2), depending upon the tumor cell line tested. Detailed structure-activity relationships of the new analogues were studied. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.001

文献信息

• 5-(9-ACRIDINYLAMINO)-TOLUIDINE COMPOUNDS
  申请人：——

  公开号：US20040198765A1

  公开（公告）日：2004-10-07

  This invention relates to 9-anilinoacridine compounds, and more particularly to their synthesis and their use in pharmaceutical compositions for treating diseases.

  这项发明涉及9-苯胺基吖啶化合物，更具体地涉及它们的合成以及它们在制备治疗疾病的药物组合物中的应用。
• US6821983B2
  申请人：——

  公开号：US6821983B2

  公开（公告）日：2004-11-23
• New analogues of AHMA as potential antitumor agents: synthesis and biological activity
  作者：Jang-Yang Chang、Chyun-Feng Lin、Wen-Yu Pan、Valeriy Bacherikov、Ting-Chao Chou、Ching-Huang Chen、Huajin Dong、Shu-Yun Cheng、Tsong-Jen Tasi、Yi-Wen Lin、Kuo-Tung Chen、Li-Tzong Chen、Tsann-Long Su

  DOI：10.1016/j.bmc.2003.09.001

  日期：2003.11

  A series of new analogues of 3-(9-acridinylamino)-5-hydroxymethylaniline (AHMA, 1) and AHMA-ethylcarbamate (2) were synthesized by introducing an O-alkylcarboxylic acid esters to the CH2OH function, displacing the CH2OH function with a dimethylaminocarboxamido group or with a methyl function introduced at the meta-, para- or ortho-position to the NH2 group to form 5-(9-acridinylamino)-m-toluidines (AMTs), 5-(9-acridinylamino)-p-toluidines (APTs) or 5-(9-acridinylamino)-o-toluidines (AOTs), respectively. The inhibitions of a variety of human tumor cell growth, interactions with DNA as well as inhibitory effect against topoisomerase 11 (Topo 11) of these new agents were studied. Among AMT, APT and AOT derivatives with dimethylaminoethylcarboxamido and Me at C4 and C5 of acridine moiety (i.e., 21c, 23c and 26c) were more cytotoxic than AHMA (1) and AHMA-ethylcarbamate (2), depending upon the tumor cell line tested. Detailed structure-activity relationships of the new analogues were studied. (C) 2003 Elsevier Ltd. All rights reserved.