- A high-efficient environment friendly preparation method of quinolone ciprofloxacin drug (by machine translation)
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The invention discloses a high-efficient environmental protection quinolone ciprofloxacin preparation method of drug, is fluorobenzene formyl ethyl acetate, the original carboxylic acid triethyl amine compound as a raw material, the three raw materials into the reactor at a temperature of 90 - 150 °C reaction under 20 - 30 H prepare get quinolone basic parent ring, then adding piperazine, to aminocapronitrile as the solvent, the temperature of the reflux reaction 20 - 28 of H, continue adding 50% sodium hydroxide solution is carboxyl ester hydrolysis to obtain the target compound. The invention is simple in raw material market can buy price is cheap; multi-step reaction link together a pan operation intermediate does not need to separate operation, the reaction process is efficient labor-saving; the whole process of transformation efficiency is high, the final product does not need chromatographic treatment is simple washing can get the pure compound; safety in the course of reaction, after-treatment does not need the eluent separation only needs to ethyl acetate, petroleum ether and methanol washing and can be recycled can be pollution prevention; green reaction process, only ethanol by-product, the atom economy is high; quinolone compounds and high utility value, is important trovafloxacins antibacterial drug composition structure. (by machine translation)
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Paragraph 0026; 0027
(2019/01/04)
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- Synthesis, molecular docking and biological evaluation of quinolone derivatives as novel anticancer agents
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A series of novel quinolone derivatives (8a-j) were synthesized, and their anticancer activities were tested in human cancer cell lines, human lung carcinoma cell (A549), human promyelocytic leukemia cell (HL-60), and human cervical cancer cell (Hela). Compound 8i was found to be 5-times more potent in cellkilling activity for cell lines A549, HL-60, and Hela than the positive control irinotecan or cisplatin, with IC50 of 0.009, 0.008 and 0.010 μM, respectively. The docking study revealed that compound 8i might have strong interactions with the active site of DNA-topoisomerase I.
- Li, Jie,Zheng, Tu-Cai,Jin, Yi,Xu, Jian-Guo,Yu, Jian-Gang,Lv, Yan-Wen
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- NOVEL METHOD OF SYNTHESIS OF FLUOROQUINOLONES
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The invention relates to a method of preparation of fluoroquinolones of formula (I) from compounds of formula (II): in which R1, R2, R3, R4, R5, R6, R7, and X are as defined in Claim 1.
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Page/Page column 6; 9
(2009/04/24)
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- Regioselective nucleophilic substitution of halogen derivatives of 1-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids
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The rate of the nucleophilic displacement of the fluoro atom of 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate could be enhanced either by the introduction of further fluoro atom(s) into position(s) 6 and/or 8, or by the formation of a boron chelate (e.g. 3). The regioselectivity of the nucleophilic substitution of the chloro atom in 1-substituted 6-fluoro-7-chloro-4-oxo-1,4dihydroquinoline-3-carboxylic acids could also be enhanced by the formation of a boron chelate (e.g. 7).
- Hermecz, Istvan,Vasvari-Debreczy, Lelle,Podanyi, Benjamin,Kereszturi, Geza,Balogh, Maria,Horvath, Agnes,Varkonyi, Peter
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p. 1111 - 1116
(2007/10/03)
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- A solid phase approach to quinolones using the DIVERSOMER technology
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The first example of a library of the quinolone antibacterial agents prepared by solid phase organic synthesis is described. Results of these studies and the parallel synthesis, isolation, purification and analysis of eight quinolones are discussed.
- MacDonald, Alasdair A.,DeWitt, Sheila H.,Hogan, Eleonora M.,Ramage, Robert
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p. 4815 - 4818
(2007/10/03)
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- Effect of Lipophilicity at N-1 on Activity of Fluoroquinolones against Mycobacteria
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The dramatic increase in drug resistant Mycobacterium tuberculosis has caused a resurgence in research targeted toward these organisms.As part of a systematic study to optimize the quinolone antibacterials against mycobacteria, we have prepared a series of N-1-phenyl-substituted derivatives to explore the effect of increasing lipophilicity on potency at this position.The compounds, synthesized by the modification of a literature procedure, were evaluated for activity against Gram-negative and Gram-positive bacteria, Mycobacterium fortuitum and Mycobacterium smegmatis, and the results correlated with log P, pKa, and other attributes.The activity of the compounds against the rapidly growing, less hazardous organism M. fortuitum was used as a measure of M. tuberculosis activity.The results demonstrate that increasing lipophilic character by itself does not correlate with increased potency against mycobacteria.Rather, intrinsic activity against Gram-negative and/or Gram-positive bacteria is the governing factor for corresponding activity against mycobacteria.
- Renau, Thomas E.,Sanchez, Joseph P.,Shapiro, Martin A.,Dever, Julie A.,Gracheck, Stephen J.,Domagala, John M.
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p. 2974 - 2977
(2007/10/02)
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- Antimicrobial 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds and compositions thereof
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Novel 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds of the formula: STR1 wherein R is hydrogen atom or fluorine atom, R° is hydroxy, fluorine atom or an alkanoyloxy having 1 to 6 carbon atoms, and X1 is hydrogen atom or fluorine atom, and a pharmaceutically acceptable salt thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition comprising as an active ingredient said 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds or a pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable diluent or carrier.
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- Synthesis and Structure-Activity Relationships of Novel Arylfluoroquinolone Antibacterial Agents
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A series of novel arylfluoroquinolones has been prepared.These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position.Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl.The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials.As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.
- Chu, Daniel T. W.,Fernandes, Prabhavathi B.,Claiborne, Akiyo K.,Pihuleac, Eva,Nordeen, Carl W.,et al.
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p. 1558 - 1564
(2007/10/02)
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