Anti-tumor compounds
A compound and chemical formula technology, applied in the field of anti-tumor compounds, can solve problems such as limiting efficacy in vivo
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Embodiment 1
[0052] Example 1: (7-methoxy-imidazo[1,2-a]pyridine-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone ((7-methoxy- Synthesis of imidazo[1,2-a]pyridin-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone)(Compound 1)
[0053]According to Luo Bo et al. in "Journal of Bioorganic Medicinal Chemistry" 1999, 9 (1), 97-102 pages (Loeber, S., et al., Bioorg Med Chem Lett 1999, 9 (1), 97-102) 7-Methoxy-imidazo[1,2-a]pyridine (7-Methoxyimidazo[1,2-a]pyridine) was prepared by the method described above.
[0054] Mix 7-methoxy-imidazo[1,2-a]pyridine (621 mg, 4.2 mmol) with POCl in dimethylformamide (4 mL) 3 (16.8 mmol). The reaction mixture was heated at 90 °C for 24 hours and then cooled to room temperature. The solvent was removed in vacuo to give an oil. The oil was purified on a silica gel column eluting with EtOAc / hexanes (1:1) to afford 7-methoxy-imidazo[1,2-a]pyridine-3-carboxylic acid indole (7-methoxyimidazo [1,2-a]pyridine-3-carbaldehyde) (508 mg, 69%).
[0055] Into a dry flask equipped wit...
Embodiment 2
[0058] Example 2: (7-methoxy-2-methyl-imidazo[1,2-a]pyridine-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone ( Compound 2) Synthesis of ((7-methoxy-2-methyl-imidazo[1,2-a]pyridin-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone)
[0059] 4-methoxy-2-aminopyridine (4-methoxy-2-aminopyridine) (1.07 g, 8.6 mmol) in EtOH (50 mL) was mixed with ethyl 2-chloroacetoacetate (5.4 The mixture of g) was refluxed for 24 hours. The reaction mixture was then concentrated to half its volume with CH 2 Cl 2 Extraction, first using brine and then washing with water, passing through anhydrous MgSO 4 dry. The solvent was removed in vacuo and the residue was treated with ethyl acetate (EtOAc) followed by MeOH / CH 2 Cl 2 (1:9) elution for purification to provide 7-methoxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate (7-methoxy-2-methylimidazo[1,2 -a] pyridine-3-carboxylate) (2.71 g, 90%).
[0060] As the product mixture (0.340 g, 1.04 mmol) in THF (15 mL) at 0 °C N 2 Stir on low for 10 minutes. Add lit...
Embodiment 3
[0063] Example 3: (6-methoxy-3a, 7a-dihydro-1H-indazole-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone ((6-methoxy Synthesis of -3a,7a-dihydro-1H-indazol-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone) (compound 3)
[0064] The mixture (0.200g, 1.04mmol) of 6-methoxy-1H-indazole-3-carboxylic acid (6-methoxy-1H-indazole-3-carboxylic acid) in THF (15mL) was at 0 ℃ N 2 Stir for 10 minutes. Add lithium aluminum hydride (LAH), in N 2 The mixture was stirred overnight at room temperature. Then, add NH 4 Cl aqueous solution (5 mL), the reaction mixture was concentrated to half its volume and extracted with ethyl acetate (EtOAc). The organic layer was washed with brine and water, and anhydrous MgSO 4 After drying, the solvent was removed in vacuo to yield a residue. MnO was stirred at 0°C 2 (0.680g, 7.8mmol) was added to anhydrous CH 2 C1 2 (15 mL) of the residue. After the addition, the mixture was stirred at room temperature for 8 hours, and the mixture was diluted with anhydrous di...
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