C3/C3 fluoroquinolone dimmer derivative using oxadiazole as connection chain as well as preparation method and application thereof
A technology of quinolone dimer and oxadiazole, which is applied in the field of pharmaceutical chemical synthesis, can solve the problems that have not been reported, and achieve the effects of strong anti-tumor activity, strong growth inhibitory activity, and strong cytotoxicity
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Embodiment 1
[0038] Preparation of 1-ethyl-6-fluoro-7-piperazin-1-yl-4(1H)-quinolinone-3-carboxhydrazide (norfloxacin hydrazide 1)
[0039] Norfloxacin (50 g, 157 mmol) was dissolved in 100 mL of 80% hydrazine hydrate, refluxed for 18 hours, cooled to room temperature, distilled under reduced pressure until evaporated to dryness, and the residue was recrystallized with 300 mL of absolute ethanol to obtain a yellow solid 1, Yield 74%. mp 186~187℃; IR(KBr)v: 3456, 2897, 1648, 1567, 1527, 1473, 1255, 869cm -1 ; 1 H NMR (DMSO-d 6 )δ: 10.56 (brs, 1H, CONH), 8.86 (s, 1H, 2-H), 7.86 (d, 1H, 5-H), 7.24 (d, 1H, 8-H), 4.53 (brs, 2H , NH 2 ), 4.62 (q, 2H, NCH 2 ), 3.32(t, 4H, piperazine-H), 2.67(t, 4H, piperazine-H), 1.36(t, 3H, CH 3 ); MS m / z: 356 (M+Na), 334 (M+H); Anal.calcd for C 16 h 20 FN5 o 2 : C 57.65, H 6.05, N 21.01; found C 57.84, H 6.15, N 21.24.
Embodiment 2
[0041] Preparation of 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4(1H)-quinolinone-3-carboxhydrazide (pefloxacin hydrazide 2)
[0042] Using pefloxacin as raw material, compound 2 was obtained by the same preparation method as in Example 1, with a yield of 68%. mp192~194℃; IR(KBr)v: 3387, 3025, 1638, 1557, 1525, 1456, 1255, 886cm -1 ; 1 H NMR (DMSO-d 6 )δ: 10.46 (brs, 1H, CONH), 8.87 (s, 1H, 2-H), 7.82 (d, 1H, 5-H), 7.32 (d, 1H, 8-H), 4.56 (brs, 2H , NH 2 ), 4.42 (q, 2H, NCH 2 ), 3.35(t, 4H, piperazine-H), 2.66(t, 4H, piperazine-H), 2.37(s, 3H, N-CH 3 ), 1.34(t, 3H, CH 3 ); MS m / z: 348 (M+H); Anal.calcd for C 17 h 22 FN 5 o 2 : C58.78, H 6.38, N 20.16; found C 58.94, H 6.20, N 20.40.
Embodiment 3
[0044] Preparation of 1-cyclopropyl-6-fluoro-7-piperazin-1-yl-4-(1H)-quinolinone-3-carboxhydrazide (ciprofloxacin hydrazide 3)
[0045] Using ciprofloxacin as raw material, compound 3 can be obtained according to the same preparation method as in Example 1, with a yield of 70%. mp226~227℃; IR(KBr)v: 3428, 3309, 2940, 2834, 1661, 1626, 1471cm -1 ; 1 H NMR (DMSO-d 6 )δ: 1.20~1.35(m, 4H, cyclopropane-H), 3.09~3.12(m, 4H, piperazine-H), 3.25~3.27(m, 4H, piperazine-H), 3.45~3.51(m, 1H , cyclopropane-H), 4.45 (brs, 2H, NH 2 ), 7.32(d, 1H, 8-H), 8.01(d, 1H, 5-H), 8.77(s, 1H, 2-H), 10.83(s, 1H, CONH); MS m / z: 346 (M+H); Anal.calcd for C 17 h 20 FN 5 o 2 : C 59.12, H 5.84, N 20.28; found C 59.36, H 5.67, N 20.46.
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