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. 2022 Jul 23;27(15):4723. doi: 10.3390/molecules27154723

Table 28.

Four-component synthesis and anticancer activity of pyranopyrazole derivatives 96.

graphic file with name molecules-27-04723-i042.jpg
Compound R Yield 96 (%) IC50 (μg/mL)
Method A Method B Hep3B
96a 3-HOC6H4 88 82 32
96b 4-BrC6H4 82 80 16
96c 3-BrC6H4 80 77 10
96d 3-NO2C6H4 86 81 32
96e 3-Thiophenyl 88 80 24
96f 2-Pyrrolyl 85 80 128
96g 3-Indolyl 81 79 64
96h 4-ClC6H4 77 70 96
96i 2-IC6H4 80 75 96
96j C6H5 86 81 128
96k n-Butyl 82 83 20
96l 4-MeC6H4 88 87 20
96m 4-Pyridinyl 94 85 48
96n 2-FC6H4 90 87 32

Method A: Aldehyde 1 (2.2 mmol), malononitrile 2 (2.2 mmol), hydrazine hydrate 4 (2.0 mmol), ethyl acetoacetate 3 (2.0 mmol), Et3N (3.0 mmol), EtOH (4 mL), 1–2 h, r.t. Method B: Aldehyde 1 (2.2 mmol), malononitrile 2 (2.2 mmol), hydrazine hydrate 4 (2.0 mmol), ethyl acetoacetate 3 (2.0 mmol), Et3N (3.0 mmol), EtOH (4 mL), 3–5 min, 60 °C, MWI.