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13
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60349096755
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2 (acetone/petroleum, V:V = 2:1) to give 9 as a colorless solid.
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2 (acetone/petroleum, V:V = 2:1) to give 9 as a colorless solid.
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14
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60349086255
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9a: MP 53-54 °C; ESI-MS: 455.0 (C24H17F4N3O2, M+H], 1H NMR (CDCl3, 500 MHz, δppm, 2.32 (s, 3H, Me, 3.01 (dd, 1H, J, 18.2 and 3.1 Hz, pyrazole, 4-Ha, 3.34 (dd, 1H, J, 18.2 and 11.1 Hz, pyrazole, 4-Hb, 5.63 (dd, 1H, J, 11.1 and 3.1 Hz, pyrazole, 5-H, 6.10 (d, 1H, J, 1.6 Hz, furan, 6.32 (d, 1H, J, 3.2 Hz, furan, 7.06-7.97 (m, 9H, furan and ArH, 13C NMR CDCl3, 125 MHz, δppm, 5.2, 39.3, 53.8, 106.7, 110.8, 116.5, 119.3, 124.0, 125.4, 125.5, 126.0, 126.5, 128.7, 129.3, 130.0, 131.4, 131.7, 133.0, 139.1, 142.1, 152.0, 152.9, 159.6, 161.0
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3, 125 MHz, δppm): 5.2, 39.3, 53.8, 106.7, 110.8, 116.5, 119.3, 124.0, 125.4, 125.5, 126.0, 126.5, 128.7, 129.3, 130.0, 131.4, 131.7, 133.0, 139.1, 142.1, 152.0, 152.9, 159.6, 161.0.
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15
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60349088976
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9b: MP 55-56 °C; ESI-MS: 464.0 (C26H20F3N3O2, M+H], 1H NMR (CDCl3, 500 MHz, δppm, 2.38 (s, 3H, Me, 3.00 (dd, 1H, J, 18.2 and 3.1 Hz, pyrazole, 4-Ha, 3.38 (dd, 1H, J, 18.2 and 11.1 Hz, pyrazole, 4-Hb, 5.48-5.56 (dd, 2H, J, 10.5 and 1.3 Hz, double bond, long}CH2, 5.69 (dd, 1H, J, 11.1 and 3.1 Hz, pyrazole, 5-H, 6.14 (d, 1H, J, 1.6 Hz, furan, 6.30 (d, 1H, J, 3.2 Hz, furan, 6.86 (dd, 1H, J, 17.2 and 1.3 Hz, double bond, long}CH, 7.21-7.90 (m, 9H, furan and ArH, 13C NMR CDCl3, 125 MHz, δppm, 5.8, 39.0, 53.6, 106.6, 110.5, 115.2, 119.0, 125.7, 125.8, 126.2, 127.6, 128.0, 128.6, 129.1, 129.3, 130.1, 131.9, 133.1, 134.8, 135.1, 138.0, 138.6, 142.0, 151.7, 152.5, 159.3
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3, 125 MHz, δppm): 5.8, 39.0, 53.6, 106.6, 110.5, 115.2, 119.0, 125.7, 125.8, 126.2, 127.6, 128.0, 128.6, 129.1, 129.3, 130.1, 131.9, 133.1, 134.8, 135.1, 138.0, 138.6, 142.0, 151.7, 152.5, 159.3.
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16
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60349128045
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9c: MP 54-55 °C; ESI-MS: 468.1 (C25H20F3N3O3, M+H], 1H NMR (CDCl3, 500 MHz, δppm, 2.34 (s, 3H, Me, 3.05 (dd, 1H, J, 18.2 and 3.1 Hz, pyrazole, 4-Ha, 3.35 (dd, 1H, J, 18.2 and 11.1 Hz, pyrazole, 4-Hb, 2.77 (s, 3H, OMe, 5.57 (dd, 1H, J, 11.1 and 3.1 Hz, pyrazole, 5-H, 6.10 (d, 1H, J, 1.6 Hz, furan, 6.33 (d, 1H, J, 3.2 Hz, furan, 6.86-7.88 (m, 9H, furan and ArH, 13C NMR CDCl3, 125 MHz, δppm, 5.3, 39.4, 53.1, 57.1, 106.3, 110.8, 111.3, 115.0, 118.8, 122.3, 125.8, 125.9, 126.4, 128.7, 128.9, 130.1, 131.7, 132.3, 133.1, 138.5, 142.5, 151.6, 152.3, 157.4, 160.1
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3, 125 MHz, δppm): 5.3, 39.4, 53.1, 57.1, 106.3, 110.8, 111.3, 115.0, 118.8, 122.3, 125.8, 125.9, 126.4, 128.7, 128.9, 130.1, 131.7, 132.3, 133.1, 138.5, 142.5, 151.6, 152.3, 157.4, 160.1.
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17
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60349094035
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9d: MP 64-65 °C; ESI-MS: 542.0 (C23H13Cl4F2N3O2, M+H], 1H NMR (CDCl3, 500 MHz, δppm, 2.38 (s, 3H, Me, 3.01 (dd, 1H, J, 18.2 and 3.1 Hz, pyrazole, 4-Ha, 3.38 (dd, 1H, J, 18.2 and 11.1 Hz, pyrazole, 4-Hb, 5.59 (dd, 1H, J, 11.1 and 3.1 Hz, pyrazole, 5-H, 6.80-7.77 (m, 7H, furan and ArH, 13C NMR CDCl3, 125 MHz, δppm, 5.6, 38.0, 44.8, 106.8, 110.9, 111.8, 115.3, 120.0, 128.0, 130.9, 131.1, 131.7, 132.1, 136.1, 137.2, 137.9, 138.9, 139.1, 152.5, 157.8, 160.3, 162.1, 166.2
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3, 125 MHz, δppm): 5.6, 38.0, 44.8, 106.8, 110.9, 111.8, 115.3, 120.0, 128.0, 130.9, 131.1, 131.7, 132.1, 136.1, 137.2, 137.9, 138.9, 139.1, 152.5, 157.8, 160.3, 162.1, 166.2.
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18
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60349130501
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9e: MP 65-66 °C; ESI-MS: 574.7 (C24H14Cl4F3N3O2, M+H], 1H NMR (CDCl3, 500 MHz, δppm, 2.32 (s, 3H, Me, 3.05 (dd, 1H, J, 18.2 and 3.1 Hz, pyrazole, 4-Ha, 3.30 (dd, 1H, J, 18.2 and 11.1 Hz, pyrazole, 4-Hb, 5.62 (dd, 1H, J, 11.1 and 3.1 Hz, pyrazole, 5-H, 7.22-7.81 (m, 8H, furan and ArH, 13C NMR CDCl3, 125 MHz, δppm, 5.8, 38.3, 45.1, 110.8, 115.7, 119.2, 125.8, 126.7, 128.1, 129.6, 129.7, 130.8, 133.5, 134.5, 135.6, 135.7, 136.3, 139.4, 139.5, 152.3, 157.2, 160.0, 162.1, 166.2
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3, 125 MHz, δppm): 5.8, 38.3, 45.1, 110.8, 115.7, 119.2, 125.8, 126.7, 128.1, 129.6, 129.7, 130.8, 133.5, 134.5, 135.6, 135.7, 136.3, 139.4, 139.5, 152.3, 157.2, 160.0, 162.1, 166.2.
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19
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60349104618
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9f: MP 65-67 °C; ESI-MS: 532.7 (C25H17Cl4N3O2, M+H], 1H NMR (CDCl3, 500 MHz, δppm, 2.37 (s, 3H, Me, 3.03 (dd, 1H, J, 18.2 and 3.1 Hz, pyrazole, 4-Ha, 3.35 (dd, 1H, J, 18.2 and 11.1 Hz, pyrazole, 4-Hb, 5.56-5.61 (dd, 2H, J, 10.5 and 1.3 Hz, double bond, long}CH2, 5.69 (dd, 1H, J, 11.1 and 3.1 Hz, pyrazole, 5-H, 6.96 (dd, 1H, J, 17.2 and 1.3 Hz, double bond, long}CH, 7.25-7.84 (m, 8H, furan and ArH, 13C NMR CDCl3, 125 MHz, δppm, 5.5, 38.8, 45.4, 110.6, 114.5, 115.8, 126.8, 127.0, 127.5, 128.0, 128.8, 129.3, 130.6, 132.5, 134.8, 135.5, 135.6, 135.7, 136.8, 137.5, 138.3, 139.2, 152.8, 158.1, 161.1
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3, 125 MHz, δppm): 5.5, 38.8, 45.4, 110.6, 114.5, 115.8, 126.8, 127.0, 127.5, 128.0, 128.8, 129.3, 130.6, 132.5, 134.8, 135.5, 135.6, 135.7, 136.8, 137.5, 138.3, 139.2, 152.8, 158.1, 161.1.
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20
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60349086256
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9g: MP 80-81 °C; ESI-MS: 546.0 (C23H17F2N5O6S, M+H], 1H NMR (CDCl3, 500 MHz, δppm, 2.35 (s, 3H, Me, 3.08 (dd, 1H, J, 18.2 and 3.1 Hz, pyrazole, 4-Ha, 3.35 (dd, 1H, J, 18.2 and 11.1 Hz, pyrazole, 4-Hb, 5.67 (dd, 1H, J, 11.1 and 3.1 Hz, pyrazole, 5-H, 6.56 (brs, 2H, NH2, 6.71-7.87 (m, 9H, furan and ArH, 13C NMR CDCl3, 125 MHz, δppm, 5.7, 38.9, 58.2, 105.4, 106.3, 111.9, 115.8, 117.6, 119.6, 120.7, 121.6, 125.6, 127.0, 130.9, 131.3, 132.7, 139.2, 153.3, 153.7, 154.6, 159.1, 161.6, 165.2
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3, 125 MHz, δppm): 5.7, 38.9, 58.2, 105.4, 106.3, 111.9, 115.8, 117.6, 119.6, 120.7, 121.6, 125.6, 127.0, 130.9, 131.3, 132.7, 139.2, 153.3, 153.7, 154.6, 159.1, 161.6, 165.2.
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21
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60349109680
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9h: MP 82-83 °C; ESI-MS: 577.1 (C24H18F3N5O6S, M+H], 1H NMR (CDCl3, 500 MHz, δppm, 2.30 (s, 3H, Me, 3.00 (dd, 1H, J, 18.2 and 3.1 Hz, pyrazole, 4-Ha, 3.31 (dd, 1H, J, 18.2 and 11.1 Hz, pyrazole, 4-Hb, 5.69 (dd, 1H, J, 11.1 and 3.1 Hz, pyrazole, 5-H, 6.69 (brs, 2H, NH2, 7.19-7.85 (m, 10H, furan and ArH, 13C NMR CDCl3, 125 MHz, δppm, 5.4, 39.3, 58.0, 106.7, 116.8, 116.9, 118.4, 119.5, 121.9, 126.7, 126.8, 126.9, 130.6, 131.1, 131.4, 132.5, 132.6, 133.8, 139.9, 153.0, 153.8, 155.0, 159.0, 161.4
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3, 125 MHz, δppm): 5.4, 39.3, 58.0, 106.7, 116.8, 116.9, 118.4, 119.5, 121.9, 126.7, 126.8, 126.9, 130.6, 131.1, 131.4, 132.5, 132.6, 133.8, 139.9, 153.0, 153.8, 155.0, 159.0, 161.4.
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22
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60349095257
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MH medium (Mueller-Hinton medium: casein hydrolysate 17.5 g, soluble starch 1.5 g, beef extract 1000 mL, The MICs of the test compounds were determined by a colorimetric method using the dye MTT. A stock solution of the synthesized compound (100 μg/mL) in DMSO was prepared and graded quantities of the test compounds were incorporated in specified quantity of sterilized liquid MH medium. A specified quantity of the medium containing the compound was poured into microtitration plates. Suspension of the microorganism was prepared to contain approximately 105 cfu/mL and applied to microtitration plates with serially diluted compounds in DMSO to be tested and incubated at 37 °C for 24 h After the MICs were visually determined on each of the microtitration plates, 50 μL of PBS (Phosphate Buffered Saline 0.01 mol/L, pH 7.4:Na2HPO4·12H2O 2.9 g, KH2PO4 0.2 g, NaCl 8.0 g, KCl 0.2 g, distilled water 1000 mL) conta
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4 0.2 g, NaCl 8.0 g, KCl 0.2 g, distilled water 1000 mL) containing 2 mg of MTT/mL was added to each well. Incubation was continued at room temperature for 4-5 h. The content of each well was removed, and 100 μL of isopropanol containing 5% 1 mol/L HCl was added to extract the dye. After 12 h of incubation at room temperature, the optical density (OD) was measured with a microplate reader at 550 nm. The MICs were observed.
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