New analogues of AHMA as potential antitumor agents: Synthesis and biological activity Journal Article
| Authors: | Chang, J. Y.; Lin, C. F.; Pan, W. Y.; Bacherikov, V.; Chou, T. C.; Chen, C. H.; Dong, H.; Cheng, S. Y.; Tasi, T. J.; Lin, Y. W.; Chen, K. T.; Chen, L. T.; Su, T. L. |
| Article Title: | New analogues of AHMA as potential antitumor agents: Synthesis and biological activity |
| Abstract: | 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. © 2003 Elsevier Ltd. All rights reserved. |
| Keywords: | controlled study; unclassified drug; human cell; drug activity; dose response; drug efficacy; nonhuman; antineoplastic agents; paclitaxel; antineoplastic agent; mouse; animals; mice; cell division; enzyme inhibition; breast cancer; animal experiment; animal model; antineoplastic activity; cytotoxicity; drug potency; tumor xenograft; cell line, tumor; drug synthesis; structure activity relation; structure-activity relationship; vinblastine; cancer inhibition; cause of death; amine; drug uptake; enzyme inhibitors; leukemia cell; tumor cell; 3 (9 acridinylamino) 5 hydroxymethylaniline; 9 anilinoacridine derivative; lymphatic leukemia; aniline compounds; tumor growth; dna topoisomerase (atp hydrolysing); acridine derivative; acridines; carbon; ester derivative; humans; human; female; article; 3 (9 acridinylamino) 5 hydroxymethylaniline ethylcarbamate; 5 (9 acridinylamino) 2 toluidine; 5 (9 acridinylamino) 3 toluidine; 5 (9 acridinylamino) 4 toluidine; drug dna interaction |
| Journal Title: | Bioorganic & Medicinal Chemistry |
| Volume: | 11 |
| Issue: | 23 |
| ISSN: | 0968-0896 |
| Publisher: | Pergamon-Elsevier Science Ltd |
| Date Published: | 2003-11-17 |
| Start Page: | 4959 |
| End Page: | 4969 |
| Language: | English |
| DOI: | 10.1016/j.bmc.2003.09.001 |
| PUBMED: | 14604658 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 12 September 2014 -- Source: Scopus |
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