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热门化合物HOT

喹啉
水杨醛
二溴甲烷
谷胱甘肽
L-乳酸
苯巴比妥
辣椒碱
非那明
百草枯
联苯烯

1-乙基-4-氧代-6,8-二氟-7-哌嗪基-1,4-二氢喹啉-3-羧酸 | 99726-76-8

分子结构分类

有机化合物 - 有机杂环化合物 - 喹啉及其衍生物

中文名称

1-乙基-4-氧代-6,8-二氟-7-哌嗪基-1,4-二氢喹啉-3-羧酸

中文别名

洛美沙星杂质6

英文名称

8-fluoronorfloxacin

英文别名

1-ethyl-6,8-difluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid；1-ethyl-6,8-difluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid；1-ethyl-6,8-difluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid；8-fluoro-norfloxacin；1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid；1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-piperazino-quinoline-3-carboxylic acid；1-Ethyl-6,8-difluoro-4-oxo-7-piperazin-4-ium-1-ylquinoline-3-carboxylate

CAS

99726-76-8

化学式

C₁₆H₁₇F₂N₃O₃

mdl

——

分子量

337.326

InChiKey

YHRXPOLYCUTZAM-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

155 °C(Solv: chloroform (67-66-3); ethanol (64-17-5))
沸点：

544.2±50.0 °C(Predicted)
密度：

1.395±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-1.1
重原子数：

24
可旋转键数：

3
环数：

3.0
sp3杂化的碳原子比例：

0.38
拓扑面积：

72.9
氢给体数：

2
氢受体数：

8

SDS

SDS：484804dfb4315234b3bd26c9814ead76

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上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
1-乙基-6,7,8-三氟-1,4-二氢-4-氧代喹啉-2-羧酸	1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid	75338-42-0	C₁₂H₈F₃NO₃	271.196
1-乙基-6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉甲酸乙酯	ethyl 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate	100501-62-0	C₁₄H₁₂F₃NO₃	299.249
6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉羧酸乙酯	ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate	79660-46-1	C₁₂H₈F₃NO₃	271.196

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[4-(2-oxopropyl)piperazin-1-yl]quinoline-3-carboxylic acid	631898-35-6	C₁₉H₂₁F₂N₃O₄	393.39
——	1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(4-phenacyl-1-piperazinyl)-quinoline-3-carboxylic acid	353793-88-1	C₂₄H₂₃F₂N₃O₄	455.461
——	7-(4-(4,6-bis(isopropylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-68-3	C₂₅H₃₂F₂N₈O₃	530.578
——	7-(4-(4,6-bis(tert-butylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-66-1	C₂₇H₃₆F₂N₈O₃	558.631
——	7-(4-(4,6-bis(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-62-7	C₂₉H₃₈F₂N₁₀O₃	612.683
——	7-(4-(4,6-bis(propylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-67-2	C₂₅H₃₂F₂N₈O₃	530.578
——	1-ethyl-6,8-difluoro-7-{4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	353793-89-2	C₂₄H₂₂F₃N₃O₄	473.452
——	7-(4-(4,6-bis(butylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-65-0	C₂₇H₃₆F₂N₈O₃	558.631
——	1-ethyl-7-{4-[2-(4-chlorophenyl)-2-oxoethyl]-1-piperazinyl}-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxykic acid	353793-90-5	C₂₄H₂₂ClF₂N₃O₄	489.906
——	7-(4-(4,6-dimorpholino-1,3,5-triazin-2-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-60-5	C₂₇H₃₂F₂N₈O₅	586.598
——	7-(4-(4,6-bis(2-morpholinoethylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-63-8	C₃₁H₄₂F₂N₁₀O₅	672.735
——	1-ethyl-6,8-difluoro-7-{4-[2-(4-methoxyphenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	353793-91-6	C₂₅H₂₅F₂N₃O₅	485.487
——	7-(4-(4,6-di(piperidin-1-yl)-1,3,5-triazin-2-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-61-6	C₂₉H₃₆F₂N₈O₃	582.653
——	7-(4-(4,6-bis(3-morpholinopropylamino)-1,3,5-triazin-2-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-64-9	C₃₃H₄₆F₂N₁₀O₅	700.789
——	7-(4-(2-chloro-6-methylpyrimidin-4-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-78-5	C₂₁H₂₀ClF₂N₅O₃	463.871
——	1-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[4-(4-methylbenzenesulfonyl)-1-piperazinyl]-3-quinolinecarboxylic acid	158437-33-3	C₂₃H₂₃F₂N₃O₅S	491.516
——	1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[4-(4-acetamidobenzenesulfonyl)-1-piperazinyl]-3-quinolinecarboxylic acid	158437-31-1	C₂₄H₂₄F₂N₄O₆S	534.541
——	1-ethyl-6,8-difluoro-7-(4-(2-(isopropylamino)-6-methylpyrimidin-4-yl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-88-7	C₂₄H₂₈F₂N₆O₃	486.522
——	7-(4-(2-(tert-butylamino)-6-methylpyrimidin-4-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-86-5	C₂₅H₃₀F₂N₆O₃	500.548
——	1-ethyl-6,8-difluoro-7-(4-(6-methyl-2-(propylamino)pyrimidin-4-yl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-87-6	C₂₄H₂₈F₂N₆O₃	486.522
——	7-(4-(2-(butylamino)-6-methylpyrimidin-4-yl)piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-85-4	C₂₅H₃₀F₂N₆O₃	500.548
——	1-ethyl-6,8-difluoro-7-(4-(6-methyl-2-(4-methylpiperazin-1-yl)pyrimidin-4-yl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-82-1	C₂₆H₃₁F₂N₇O₃	527.574
——	1-ethyl-6,8-difluoro-7-(4-(6-methyl-2-(2-morpholinoethylamino)pyrimidin-4-yl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-83-2	C₂₇H₃₃F₂N₇O₄	557.6
——	1-ethyl-6,8-difluoro-7-(4-(6-methyl-2-morpholinopyrimidin-4-yl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-80-9	C₂₅H₂₈F₂N₆O₄	514.532
——	1-ethyl-6,8-difluoro-7-(4-(6-methyl-2-(piperidin-1-yl)pyrimidin-4-yl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-81-0	C₂₆H₃₀F₂N₆O₃	512.559
——	1-ethyl-6,8-difluoro-7-(4-(6-methyl-2-(3-morpholinopropylamino)pyrimidin-4-yl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	1293992-84-3	C₂₈H₃₅F₂N₇O₄	571.627
——	methyl 1-ethyl-7-[N-(2-ethyloxycarbonylaminoethyl)amino]-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate	——	C₁₈H₂₂FN₃O₅	379.388

反应信息

作为反应物：

描述：

1-乙基-4-氧代-6,8-二氟-7-哌嗪基-1,4-二氢喹啉-3-羧酸在碳酸氢钠作用下，以甲醇、二氯甲烷、 N,N-二甲基甲酰胺为溶剂，反应 24.0h，生成 (Z)-1-ethyl-6,8-difluoro-4-oxo-7-[4-(2-phenyl-2-thiosemicarbazonoethyl)piperazinyl]-1,4-dihydroquinoline-3-carboxylic acid

参考文献：

名称：

Synthesis and Antibacterial Evaluation of Certain Quinolone Derivatives

摘要：

A number of 7-substituted quinolone derivatives were synthesized and evaluated for antibacterial and cytotoxic activities. Preliminary results indicated that most compounds tested in this study demonstrated better activity against methicillin-resistant Staphylococcus aureus than norfloxacin. Among them, 1-(4-amino-2-fluorophenyl)-6-fluoro-1,4-dihydro-7-{4-[2-(4-methoxyphenyl)-2-hydroxyiminoethyl]-1-piperazinyl}-4-oxo-3-quinolinecarboxylic acid (11d) and its ketone precursor 10d exhibited significant activities against Klebsiella pneumoniae, methicillin-resistant S. aureus, erythromycin- and ampicillin-resistant Streptococcus pneumoniae, and vancomycin-resistant Enterococcus faecalis. Due to strong cytotoxicities of lid (a mean log GI(50) of -5.40), compound 10d, with good antibacterial activities and low cytotoxicities (a mean log GI(50) of -4.67), is a more potential drug candidate.

DOI：

10.1021/jm0100335
作为产物：

描述：

2,3,4-三氟苯胺在盐酸、水、 potassium carbonate 作用下，以二苯醚、溶剂黄146 、 N,N-二甲基甲酰胺、乙腈为溶剂，反应 29.0h，生成 1-乙基-4-氧代-6,8-二氟-7-哌嗪基-1,4-二氢喹啉-3-羧酸

参考文献：

名称：

Synthesis and antibacterial evaluation of novel 8-fluoro Norfloxacin derivatives as potential probes for methicillin and vancomycin-resistant Staphylococcus aureus

摘要：

A series of novel 8-fluoro Norfloxacin derivatives and the hybrids of its piperazinyl derivatives incorporated with 1,3,5-triazine and pyrimidine were synthesized. All the above compounds were evaluated for their antibacterial activity against Klebsiella pneumoniae, methicillin-resistant Staphylococcus aureus and methicillin & vancomycin-resistant S. aureus. Among all, compounds having Morpholine, N-methyl/phenyl/benzyl/pyrimidinyl piperazines and n-butylamine substitution at C-7 position, have shown increased potency in comparison to norfloxacin and ciprofloxacin. (c) 2011 Published by Elsevier Masson SAS.

DOI：

10.1016/j.ejmech.2011.01.044

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文献信息

Microwave assisted amination of quinolone carboxylic acids: an expeditious synthesis of fluoroquinolone antibacterials

作者：P.Ganapati Reddy、S Baskaran

DOI：10.1016/s0040-4039(01)01385-5

日期：2001.9

A facile amination of quinolone carboxylic acids to fluoroquinolone antibacterials under microwave irradiation is described.

描述了在微波辐射下将喹诺酮羧酸容易地胺化为氟喹诺酮抗菌剂。
NOVEL METHOD OF SYNTHESIS OF FLUOROQUINOLONES

申请人：BERTHON-CEDILLE Laurence

公开号：US20090054643A1

公开（公告）日：2009-02-26

The invention relates to a method of preparation of fluoroquinolones of formula (I) from compounds of formula (II): in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and X are as defined in Claim 1.

该发明涉及一种从化合物（II）制备化合物（I）的氟喹诺酮的方法：其中R1、R2、R3、R4、R5、R6、R7和X的定义如权利要求1中所述。
6-fluoro-1,4-dihydro-7-[4-(2-hydroxyiminoethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid derivatives, their preparation and pharmaceutical compositions

申请人：Pharmaceutical Industry Technology

公开号：US20020061895A1

公开（公告）日：2002-05-23

The present invention discloses a novel 6-fluoro-1,4-dihydro-7-[4-(2-hydroxyiminoethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid derivatives (formula I), with a process for their preparation, and with pharmaceutical compositions containing them as the active ingredient for the treatment of bacterial infections and/or renal cancer diseases. 1

本发明揭示了一种新颖的6-氟-1,4-二氢-7-[4-(2-羟基亚胺基乙基)-1-哌嗪基]-4-氧喹啉-3-羧酸衍生物（式I），以及它们的制备方法和含有它们作为活性成分的药物组合物，用于治疗细菌感染和/或肾癌疾病。
Unexpected Photoreactions of Some 7-Amino-6-fluoroquinolones in Phosphate Buffer

作者：Elisa Fasani、Mariella Mella、Sandra Monti、Angelo Albini

DOI：10.1002/1099-0690(200101)2001:2<391::aid-ejoc391>3.0.co;2-r

日期：2001.1

the heteroaryl ring and oxidative fragmentation of the piperazine side chain. This unusual reaction contrasts with the fluorine atom substitution observed in neat water. The results of steady-state and time-resolved experiments are consistent with initiation of the process by electron-transfer quenching of the triplet state of these heterocycles by the phosphate anion. For one of the compounds, a transient

某些 6-fluoro-7-piperazino-4-quinolone-3- 羧酸在磷酸盐缓冲液中的辐照产物产生于杂芳环的还原脱氟和哌嗪侧链的氧化断裂的组合。这种不寻常的反应与在纯水中观察到的氟原子取代形成鲜明对比。稳态和时间分辨实验的结果与通过磷酸根阴离子对这些杂环的三重态进行电子转移猝灭所引发的过程是一致的。对于其中一种化合物，以前归因于脱氟阳离子的瞬态带 (λmax = 670 nm) 现在必须重新分配给自由基阴离子。该中间体进行环的低效还原脱氟。进行中，
Quinolonecarboxylic acid derivatives

申请人：Senju Pharmaceutical Co., Ltd.

公开号：US05753658A1

公开（公告）日：1998-05-19

Presented is a novel quinolonecarboxylic acid derivative of the formula I and its pharmaceutically acceptable salt: ##STR1## wherein R.sub.1 is hydrogen, halogen or lower alkoxy, R.sub.2 is hydrogen, lower alkyl, lower alkoxy, --NH.sub.2, --NHCOCH.sub.3 or halogen, R.sub.3 is lower alkyl, and z is a group represented by the formula II or III: ##STR2## wherein R.sub.4 and R.sub.5 are identical or different and are hydrogen or lower alkyl. A method of preparation of these compound and a method of treatment of diseases caused by bacterial infection are also presented.

介绍一种新型喹诺酮羧酸衍生物及其药用盐，其化学式为I：##STR1## 其中，R.sub.1为氢、卤素或低碳基氧基，R.sub.2为氢、低碳基、低碳基氧基、--NH.sub.2、--NHCOCH.sub.3或卤素，R.sub.3为低碳基，z为公式II或III所表示的基团：##STR2## 其中，R.sub.4和R.sub.5相同或不同，为氢或低碳基。还提供了这些化合物的制备方法和治疗细菌感染引起的疾病的方法。