Synthesis and evaluation of antitumor activity of 2- and 6-[(1,3-benzothiazol-2-yl)aminomethyl]-5,8-dimethoxy-1,4- naphthoquinone derivatives

Yongseog Chung, Young Kook Shin, Chang Guo Zhan, Sungduck Lee, Hoon Cho

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

2- or 6-Substituted BZT-N derivatives were synthesized, and their cytotoxic activity against cancer L1210 and SNU-1 cells was examined. The antitumor action was also assessed in mice bearing S-180 cells in peritoneal cavity. In a comparison, it was found that 6-substituted BZT-N derivatives exhibited higher potencies in both bioactivities than 2-substituted BZT-N derivatives against L1210 cells in in vitro and S-180 in vitro tests exception of compound 36. Interestingly, it was observed that 2-substituted compound 36, which has methyl group at R1 position, exhibited a better antitumor activity than 6-substituted compounds against L1210 and SNU-1 in vitro. The ED50 value of 2-substituted compound 36 against L1210 was found to be comparable to the ED50 value of adriamycin and was even better against the solid cancer cell line SNU-1. It was also observed that 2-substituted compound 36 showed better antitumor activity in mice bearing S-180 cells in the peritoneal cavity. The T/C (%) value of 2-substituted compound 36 was similar to that of adriamycin. Quantitative structure-activity relationship (QSAR) tests reveal that the experimental ED50 values against SNU-1 closely correlate with both the calculated HOMO energies (EHOMO) and the measured 1H-NMR chemical shift of 3-H (δH). The results suggests that a compound having higher EHOMO and δH values usually should have a lower ED50 (SNU-1) value.

Original languageEnglish
Pages (from-to)893-900
Number of pages8
JournalArchives of Pharmacal Research
Volume27
Issue number9
DOIs
StatePublished - Sep 30 2004

Bibliographical note

Funding Information:
This work was supported by Chungbuk University.

Keywords

  • Antitumor activity
  • Cytotoxicity
  • Naphthoquinone

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery
  • Organic Chemistry

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