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Synthesis of N2-(substituted benzyl)-3-(4-methylphenyl)indazoles as novel anti-angiogenic agents. 2006

Li-Jiau Huang, and Mei-Ling Shih, and Hua-Sin Chen, and Shiow-Lin Pan, and Che-Ming Teng, and Fang-Yu Lee, and Sheng-Chu Kuo
Graduate Institute of Pharmaceutical Chemistry, China Medical University, Taichung, Taiwan.

To search for novel compounds with potent anti-angiogenic activity, a series of N(1)-(substituted benzyl)-3-(4-methylphenyl)-1H-indazoles (16, 18, 20, 22, 24, 26, 28, 30, 32) and N(2)-(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.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D002478 Cells, Cultured Cells propagated in vitro in special media conducive to their growth. Cultured cells are used to study developmental, morphologic, metabolic, physiologic, and genetic processes, among others. Cultured Cells,Cell, Cultured,Cultured Cell
D004730 Endothelium, Vascular Single pavement layer of cells which line the luminal surface of the entire vascular system and regulate the transport of macromolecules and blood components. Capillary Endothelium,Vascular Endothelium,Capillary Endotheliums,Endothelium, Capillary,Endotheliums, Capillary,Endotheliums, Vascular,Vascular Endotheliums
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D013057 Spectrum Analysis The measurement of the amplitude of the components of a complex waveform throughout the frequency range of the waveform. (McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed) Spectroscopy,Analysis, Spectrum,Spectrometry
D018919 Neovascularization, Physiologic The development of new BLOOD VESSELS during the restoration of BLOOD CIRCULATION during the healing process. Angiogenesis, Physiologic,Angiogenesis, Physiological,Neovascularization, Physiological,Physiologic Angiogenesis,Physiologic Neovascularization,Physiological Angiogenesis,Physiological Neovascularization
D018922 HL-60 Cells A promyelocytic cell line derived from a patient with ACUTE PROMYELOCYTIC LEUKEMIA. HL-60 cells lack specific markers for LYMPHOID CELLS but express surface receptors for FC FRAGMENTS and COMPLEMENT SYSTEM PROTEINS. They also exhibit phagocytic activity and responsiveness to chemotactic stimuli. (From Hay et al., American Type Culture Collection, 7th ed, pp127-8) HL60 Cells,Cell, HL60,Cells, HL60,HL 60 Cells,HL-60 Cell,HL60 Cell
D020533 Angiogenesis Inhibitors Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. Angiogenesis Factor Inhibitor,Angiogenesis Inhibitor,Angiogenetic Antagonist,Angiogenetic Inhibitor,Angiogenic Antagonist,Angiogenic Antagonists,Angiogenic Inhibitor,Angiostatic Agent,Angiostatic Agents,Anti-Angiogenetic Agent,Anti-Angiogenic Drug,Anti-Angiogenic Drugs,Antiangiogenic Agent,Neovascularization Inhibitor,Neovascularization Inhibitors,Angiogenesis Factor Inhibitors,Angiogenetic Antagonists,Angiogenetic Inhibitors,Angiogenic Inhibitors,Antagonists, Angiogenic,Anti-Angiogenesis Effect,Anti-Angiogenesis Effects,Anti-Angiogenetic Agents,Antiangiogenesis Effect,Antiangiogenesis Effects,Antiangiogenic Agents,Inhibitors, Angiogenesis,Inhibitors, Angiogenetic,Inhibitors, Angiogenic,Inhibitors, Neovascularization,Agent, Angiostatic,Agent, Anti-Angiogenetic,Agent, Antiangiogenic,Agents, Angiostatic,Agents, Anti-Angiogenetic,Agents, Antiangiogenic,Antagonist, Angiogenetic,Antagonist, Angiogenic,Antagonists, Angiogenetic,Anti Angiogenesis Effect,Anti Angiogenesis Effects,Anti Angiogenetic Agent,Anti Angiogenetic Agents,Anti Angiogenic Drug,Anti Angiogenic Drugs,Drug, Anti-Angiogenic,Drugs, Anti-Angiogenic,Effect, Anti-Angiogenesis,Effect, Antiangiogenesis,Effects, Anti-Angiogenesis,Effects, Antiangiogenesis,Factor Inhibitor, Angiogenesis,Factor Inhibitors, Angiogenesis,Inhibitor, Angiogenesis,Inhibitor, Angiogenesis Factor,Inhibitor, Angiogenetic,Inhibitor, Angiogenic,Inhibitor, Neovascularization,Inhibitors, Angiogenesis Factor

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