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

62 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

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Indazoles
Benzoates
Nuclear magnetic resonance
Derivatives

Keywords

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

ASJC Scopus subject areas

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

Cite this

Synthesis of N2-(substituted benzyl)-3-(4-methylphenyl)indazoles as novel anti-angiogenic agents. / Huang, Li Jiau; Shih, Mei Ling; Chen, Hua Sin; Pan, Shiow Lin; Teng, Che Ming; Lee, Fang Yu; Kuo, Sheng Chu.

In: Bioorganic and Medicinal Chemistry, Vol. 14, No. 2, 15.01.2006, p. 528-536.

Research output: Contribution to journalArticle

Huang, Li Jiau ; Shih, Mei Ling ; Chen, Hua Sin ; Pan, Shiow Lin ; Teng, Che Ming ; Lee, Fang Yu ; Kuo, Sheng Chu. / Synthesis of N2-(substituted benzyl)-3-(4-methylphenyl)indazoles as novel anti-angiogenic agents. In: Bioorganic and Medicinal Chemistry. 2006 ; Vol. 14, No. 2. pp. 528-536.
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