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

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

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)


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 NH 2 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 II (Topo II) 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.

Original languageEnglish
Pages (from-to)4959-4969
Number of pages11
JournalBioorganic and Medicinal Chemistry
Issue number23
Publication statusPublished - Nov 2003
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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