Synthesis of N2-(substituted benzyl)-3-(4-methylphenyl)indazoles as novel anti-angiogenic agents

Li Jiau Huang, Mei Ling Shih, Hua Sin Chen, Shiow Lin Pan, Che Ming Teng, Fang Yu Lee, Sheng Chu Kuo

Research output: Contribution to journalArticle

64 Citations (Scopus)

Abstract

To search for novel compounds with potent anti-angiogenic activity, a series of N1-(substituted benzyl)-3-(4-methylphenyl)-1H-indazoles (16, 18, 20, 22, 24, 26, 28, 30, 32) and N2-(substituted benzyl)-3-(4-methylphenyl)-2H-indazoles (17, 19, 21, 23, 25, 27, 29, 31, and 33) were synthesized. The structures of these regioisomers were established by IR, UV, and NMR spectral data. 3-(4-Methylphenyl)-1H-indazole (6) and the N 2-substituted derivatives (17, 19, 21, 23, 25, 29, 31, 33) were evaluated for their anti-angiogenic activity. Most of them showed more prominent activity than ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3). Among these tested compounds, 2-(4-chlorobenzyl)-3-(4-methylphenyl)-2H-indazole (19), 2-(4-methylbenzyl)-3-(4-methylphenyl)-2H-indazole (25), and 2-(4-methoxybenzyl)- 3-(4-methylphenyl)-2H-indazole (31) showed significant anti-angiogenic activity and are worthy of further investigation.

Original languageEnglish
Pages (from-to)528-536
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume14
Issue number2
DOIs
Publication statusPublished - Jan 15 2006
Externally publishedYes

Keywords

  • Anti-angiogenic agents
  • N-(Substituted benzyl)-3-(4- methylphenyl)-indazoles

ASJC Scopus subject areas

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

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