Synthesis and structure-activity relationships of potential anticancer agents: Alkylcarbamates of 3-(9-acridinylamino)-5-hydroxymethylaniline Journal Article
| Authors: | Su, T. L.; Chen, C. H.; Huang, L. F.; Chen, C. H.; Basu, M. K.; Zhang, X. G.; Chou, T. C. |
| Article Title: | Synthesis and structure-activity relationships of potential anticancer agents: Alkylcarbamates of 3-(9-acridinylamino)-5-hydroxymethylaniline |
| Abstract: | 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. |
| Keywords: | controlled study; unclassified drug; human cell; doxorubicin; nonhuman; antineoplastic agents; antineoplastic agent; animal cell; mouse; animals; mice; antineoplastic activity; cancer cell culture; drug structure; drug screening assays, antitumor; drug synthesis; structure activity relation; structure-activity relationship; drug cytotoxicity; amsacrine; neoplasm transplantation; acridines; carbamates; leukemia cell line; hl-60 cells; humans; human; male; article; 3 (9 acridinylamino) 5 hydroxymethylaniline derivative; 3 (9 acridinylamino) 5 hydroxymethylaniline ethylcarbamic acid; 4' methyl 5' dimethylaminoethylcaboxamido 3 (9 acridinylamino) 5 hydroxymethylaniline ethylcarbamic acid |
| Journal Title: | Journal of Medicinal Chemistry |
| Volume: | 42 |
| Issue: | 23 |
| ISSN: | 0022-2623 |
| Publisher: | American Chemical Society |
| Date Published: | 1999-11-18 |
| Start Page: | 4741 |
| End Page: | 4748 |
| Language: | English |
| DOI: | 10.1021/jm9901226 |
| PUBMED: | 10579838 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 16 August 2016 -- Source: Scopus |
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