C3/C3 fluoroquinolone dipolymer derivative taking s-triazolo-[3,4-b][1,3,4] thiadiazole as connecting chain and preparation method and application thereof
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A quinolone dimer, thiadiazole technology, applied in the field of medicinal chemistry synthesis, can solve problems such as unreported, and achieve the effect of strong anti-tumor activity and strong anti-Gram-negative bacteria activity
Inactive Publication Date: 2010-02-17
河南省健康伟业生物医药研究股份有限公司
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Existing FQ antitumor compounds all contain one FQ unit, but compounds containing two FQ structural units in one molecule have not been reported yet. In addition, s-triazolo[3,4-b][1,3,4]thiazo Although there are a large number of synthesis report
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Embodiment 1
[0041] Preparation of 1-ethyl-6-fluoro-7-piperazin-1-yl-4(1H)-quinolinone-3-carboxhydrazide (norfloxacin hydrazide III-1)
[0042]Norfloxacin (50g, 157mmol) was dissolved in 100mL of 80% hydrazine hydrate, refluxed for 12 hours, cooled to room temperature, distilled under reduced pressure until evaporated to dryness, and the residue was recrystallized with 300mL of absolute ethanol to obtain a yellow solid III- 1. The yield is 70%. mp 186~187℃; 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).
Embodiment 2
[0044] Preparation of 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4(1H)-quinolinone-3-carboxhydrazide (pefloxacin hydrazide III-2)
[0045] Using pefloxacin as raw material, compound III-2 was obtained by the same preparation method as in Example 1, with a yield of 68%. mp192~194℃; 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).
Embodiment 3
[0047] Preparation of 1-cyclopropyl-6-fluoro-7-piperazin-1-yl-4-(1H)-quinolinone-3-carboxhydrazide (ciprofloxacin hydrazide III-3)
[0048] Using ciprofloxacin as raw material, compound III-3 can be obtained according to the same preparation method as in Example 1, with a yield of 70%. mp226~227℃; 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).
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Abstract
The invention discloses a C3/C3 fluoroquinolone dipolymer derivative taking s-triazolo-[3,4-b][1,3,4] thiadiazole as a connecting chain and a preparation method and application thereof, wherein the C3/C3 fluoroquinolone dipolymer derivative taking s-triazolo-[3,4-b][1,3,4] thiadiazole as the connecting chain is a compound having a general structure formula (I). In the general structure formula (I), R1 and R1' are independently selected from alkyl of H,C1-C10, naphthene base of C3-C10, haloalkyl of C1-C10 and substituted aryl radical or substituted heterocycle aryl radical at random; R2 and R2'are independently selected from alkyl of H,C1-C7, naphthene base of C3-C7, substituted aryl radical, substituted heterocycle aryl radical, hydrocarbon acyl or sulfonyl at random; R3 and R3' are independently selected from alkyl of H,C1-C5, naphthene base of C3-C6, substituted aryl radical or substituted heterocycle aryl radical at random; and X and Y are independently selected from CH, N or carbon atoms connected with halogen, alkyl, oxyl, sulfenyl, amino, substituted amino, substituted aryl radical or substituted heterocycle aryl radical. The C3/C3 fluoroquinolone dipolymer derivative takings-triazolo-[3, 4-b] [1, 3, 4] thiadiazole as the connecting chain can be used to prepare drugs for treating tumors and antimicrobial infection diseases.
Description
technical field [0001] The invention relates to the technical field of pharmaceutical chemical synthesis, in particular to C3 / C3 fluoroquinolone dimer derivatives with s-triazolo[3,4-b][1,3,4]thiadiazole as connecting chains and their preparation The method and the application as a medicine for preparing tumors and antimicrobial infection diseases. Background technique [0002] Fluoroquinolones (FQ) are clinical antimicrobials developed in the 1980s, represented by norfloxacin, and nearly 30 varieties have been widely used clinically. The action target of fluoroquinolones topoisomerase (TOPO) has homologous sequence similarity with TOPO of mammals, and TOPO is also a new target of antitumor drug action. Accordingly, it is important to convert antibacterial drug FQ into antitumor drug FQ A new direction of current research. At present, anti-tumor FQ compounds including bicyclic quinolones, tricyclic quinolones, tetracyclic quinolones, chiral quinolones, flavonoids and other...
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