Ciprofloxacin synthesis

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    Ciprofloxacin synthesis


    Ciprofloxacin is a fluoroquinolone (flor-o-KWIN-o-lone) antibiotic that fights bacteria in the body. It is used to treat different types of bacterial infections, including skin infections, bone and joint infections, respiratory or sinus infections, urinary tract infections, and certain types of diarrhea. Ciprofloxacin is also used to treat people who have been exposed to anthrax or certain types of plague. Ciprofloxacin should be used only for infections that cannot be treated with a safer antibiotic. Fluoroquinolone antibiotics can cause serious or disabling side effects that may not be reversible, such as tendon rupture or nerve problems. Ciprofloxacin can cause serious side effects, including tendon problems, nerve damage, serious mood or behavior changes, or low blood sugar. Stop using this medicine and call your doctor at once if you have symptoms such as: headache, hunger, irritability, numbness, tingling, burning pain, confusion, agitation, paranoia, problems with memory or concentration, thoughts of suicide, or sudden pain or movement problems in any of your joints. In rare cases, ciprofloxacin may cause damage to your aorta, which could lead to dangerous bleeding or death. This includes bone and joint infections, intra abdominal infections, certain type of infectious diarrhea, respiratory tract infections, skin infections, typhoid fever, and urinary tract infections, among others. Ciprofloxacin is used to treat a wide variety of infections, including infections of bones and joints, endocarditis, gastroenteritis, malignant otitis externa, respiratory tract infections, cellulitis, urinary tract infections, prostatitis, anthrax, and chancroid. Ciprofloxacin only treats bacterial infections; it does not treat viral infections such as the common cold. For certain uses including acute sinusitis, lower respiratory tract infections and uncomplicated gonorrhea, ciprofloxacin is not considered a first-line agent. Ciprofloxacin occupies an important role in treatment guidelines issued by major medical societies for the treatment of serious infections, especially those likely to be caused by Gram-negative bacteria, including Pseudomonas aeruginosa. For example, ciprofloxacin in combination with metronidazole is one of several first-line antibiotic regimens recommended by the Infectious Diseases Society of America for the treatment of community-acquired abdominal infections in adults. In other cases, treatment guidelines are more restrictive, recommending in most cases that older, narrower-spectrum drugs be used as first-line therapy for less severe infections to minimize fluoroquinolone-resistance development.

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    Evolution of different syntheses of ciprofloxacin are described. A high yielding two step synthesis from 2,4-dichloro-5-fluoro benzoylchloride is described. Scheme 6. Synthesis of 7-4-5-amino-1,3,4 thiadiazole-2-sulfonyl ciprofloxacin 19. Scheme 7. Synthesis of ciprofloxacin derivatives 22 using fluoroquinolone carboxylic acids 20. Scheme 8. Synthesis of symmetric ciprofloxacin dimmers 24. 1854 R. AKHTAR ET AL. Ciprofloxacin is a fluoroquinolone flor-o-KWIN-o-lone antibiotic that fights bacteria in the body. It is used to treat different types of bacterial infections, including skin infections, bone and joint infections, respiratory or sinus infections, urinary tract infections, and certain types of diarrhea.

    The condensation of 2,4-dichloro-5-fluorobenzoyl chloride (I) with diethyl malonate by means of magnesium ethoxide in ether gives diethyl 2,4-dichloro-5-fluorobenzoylmalonate (II), which is partially hydrolyzed and decarboxylated with p-toluenesulfonic acid water yielding ethyl 2,4-dichloro-5-fluorobenzoylacetate . Condensation of this with triethyl orthoformate in refluxing acetic anhydride affords ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-ethoxyacrylate (III), which is treated with cyclopropylamine (IV) in ethanol to give ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-cyclopropylaminoacrylate . The cyclization of ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-cyclopropylaminoacrylate with Na H in refluxing dioxane yields 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (V), which is finally condensed with piperazine in hot DMSO to afford the target compound ciprofloxacin. Ciprofloxacin (CP), an antibiotic has been shown to have antiproliferative and apoptotic activities in several cancer cell lines. Moreover, several reports have highlighted the interest of increasing the lipophilicity to improve the antitumor efficacy. These studies have led us to synthesize new CP derivatives of various lipophilicities and to evaluate their activity in five human cancer cell lines. With an easy and cost-efficient procedure, 31 7-((4-substituted)piperazin-1-yl) derivatives of CP were prepared that displayed IC80 mg/kg. Several derivatives displayed higher in vitro antitumor activity than parent CP however this was not dependent on the lipophilicity of the substituent.

    Ciprofloxacin synthesis

    A Rapid Total Synthesis of Ciprofloxacin. - Wiley Online Library, Synthesis of ciprofloxacin-based compounds A review

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    Camps quinoline synthesis 18 4. Biere-Seelen synthesis 19 5. Snieckus synthesis of 4-quinolones 20 6. Dieckmann Cyclization approach to 4-quinolones 20 7. Bayer Ciprofloxacin synthesis 24 8. Schwalbe Ciprofloxacin synthesis 25 9. Overview of the initial synthesis of the carboxylated quinolone to Ciprofloxacin 27 10. Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others. Contact Technical Service Bulk Ordering & Pricing Ciprofloxacin is a broad spectrum antibiotic which plays an important role in inhibiting the growth of both gram-positive and gram-negative bacteria.

     
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