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3-position substituted quinolone derivativers and its use in pharmacy

A representative compound technology, applied in the 3-position substituted quinolone derivatives and its application in medicine, can solve the problem of unreported anti-tumor activity

Inactive Publication Date: 2004-02-11
CHINA PHARM UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Russian scholars reported the preparation of 3-(2-benzimidazole)-1-methyl-4-quinolone, and synthesized corresponding pentacyclic fused compounds using this as raw material, but no antitumor activity was reported [Ukr. Khim. Zh. (Russ.), 1986, 52(7): 742-6]

Method used

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  • 3-position substituted quinolone derivativers and its use in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 1-Ethyl-3-(2-benzoimidazolyl)-6-fluoro-7-(1-piperazinyl)-4(1H)-quinolone (1)

[0036] Norfloxacin (norfloxacin) (3.19 grams, 0.1mol) and o-phenylenediamine (1.08 grams, 0.1mol) were mixed and ground in a mortar, added to the reaction bottle, 40 milliliters of polyphosphoric acid was added, and vacuum pumping Remove the air in the reaction bottle until no bubbles are generated, feed nitrogen, stir slowly to 140°C and keep warm until the reaction solution is homogeneous, then raise the temperature to 180°C and react for 4 hours, then cool down to about 100°C, and stir the reaction solution down. Put it into 250 grams of crushed ice, let it stand for cooling, adjust the pH value to 9, suction filter, and dry to obtain the crude product, DMF recrystallization, and methanol-triethylamine as the developer column chromatography to obtain 0.90 grams of off-white crystals, mp 260-2°C, yield 23.4%. IR (cm -1 ): 3923, 2947, 1630, 1563, 1542, 1527, 1492, 1255, 879; 1 HNMR (δ, pp...

Embodiment 2

[0038] 1-Ethyl-3-(2-benzoimidazolyl)-6-fluoro-7-(4-methyl-1-piperazinyl)-4(1H)-quinolone (2)

[0039] Using flufloxacin as a raw material, the preparation method is the same as in Example 1, and recrystallized with DMF. Column chromatography gave off-white solid, mp239-42°C (decomposition), yield 26.4%. IR (cm-1): 3329, 2925, 1620, 1550, 1473, 1284, 789; 1HNMR (δ, ppm, DMSO-d6): 1.44(t, 3H, -CH 3 ), 2.25(s, 3H, -CH 3 ), 2.50 (m, 4H, -CH 2 -*2), 3.27(m, 4H, -CH 2 -*2), 4.56(q, 2H, -CH 2 -), 7.12(m, 3H, 8-H and 5'-Hand 6'-H), 7.61(m, 2H, 4'-H and 7'-H), 7.95(d, 1H, 5-H) , 9.17(s, 1H, 1-H), 12.67(s, 1H, 1'-H); Formula: C 23 h 24 N 5 OF.2H 2O MW: 441.50, Anal (C%, H%, N%,) Calc: 62.57, 6.34, 15.86 Found: 62.02, 6.13, 16.26; HRMS: M + Meas 405.197192 Calc mass 405196474 Error-0.718, MS (EI, m / s): (M + ): 405 (base peak), 306

Embodiment 3

[0041] (±) 6-(2-Benzimidazolyl)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H -pyrido[1,2,3-de][1,4]benzoxazine (3)

[0042] Using ofloxacin as a raw material, the preparation method is the same as in Example 1, and recrystallized with DMF. Column chromatography gave an off-white solid, mp230-2°C, yield 21.3%.

[0043] IR (cm-1): 3332, 2930, 1620, 1575, 1550, 1473, 1285, 1259, 789; 1HNMR (δ, ppm, DMSO-d6): 1.48 (d, 3H, -CH 3 ), 2.32 (s, 3H, -CH 3 ), 2.51(s, 4H, -CH 2 -*2), 3.33(s, 4H, -CH 2 -*2), 4.39-4.59(m, 2H, -CH 2 -), 4.92(m, 1H, -CH-), 7.14(m, 2H, 5'-Hand 6'-H), 7.60(d, 3H, 4'-H, 7'-H and8-H), 9.15(sH, 5-H), 12.67(s, 1H, 1'-H); Formula: C 24 h 24 N 5 o 2 F.1.5H 2 O MW: 460.51, Anal (C%, H%, N%,) Calc: 62.60 5.90, 15.21 Found: 62.94, 5.46, 15.00; HRMS: M+Meas 433.191533 Calc mass 433.191388 Error-0.145mu, MS (EI, m / s): 433 (M+base peak).

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Abstract

The present invention discloses new quinolone derivatives with 3-position substituted by imidazol radical, benzoxazole and benzothiazole and possessing antitumor activity. The preparation process ofthe compounds is also disclosed.

Description

technical field [0001] The invention relates to a novel 3-position substituted quinolone compound and its application in the preparation of drugs for treating tumors. Background technique [0002] The common pharmacological activity of quinolones is antibacterial. According to literature reports, benzimidazole, benzoxazole and benzothiazole compounds may have topoisomerase I inhibitory activity. Russian scholars reported the preparation of 3-(2-benzimidazole)-1-methyl-4-quinolone, and synthesized corresponding pentacyclic fused compounds using this as raw material, but no antitumor activity was reported [Ukr. Khim. Zh. (Russ.), 1986, 52(7): 742-6]. Contents of the invention [0003] The technical problem to be solved by the present invention is to provide a new quinolone 3-position with antitumor activity substituted or unsubstituted benzimidazole, benzoxazole and benzothiazole substituted compound, and to provide it in the preparation of tumor treatment application in ...

Claims

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Application Information

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IPC IPC(8): A61K31/4709A61K31/496A61P35/00C07D401/04C07D413/04C07D417/04C07D498/04
Inventor 尤启冬何训贵李志裕陈晓光李燕李洪燕张文明
Owner CHINA PHARM UNIV
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