Ofloxacin

Ofloxacin is a fluoroquinolone whose primary mechanism of action is inhibition of bacterial DNA gyrase.Target: DNA gyrase Ofloxacin is a fluoroquinolone whose primary mechanism of action is inhibition of bacterial DNA gyrase. In vitro it has a broad spectrum of activity against aerobic Gram-negative and Gram-positive bacteria, although it is poorly active against anaerobes [1]. Ofloxacin, like other 4-quinolones, is unusual among front line drugs available to treat bacterial infections s

3 g of starting material 9, 10-difluoro-2, 3-dihydro-3-methyl-7-oxo-7H-pyridine[1, 2, 3, 8] - [1, 4] -benzoxazine-6-carboxylate, 4.58 water, 4.5 8 ^ methylpiperazine and 0.22 8 (81percent)Potassium hydroxide, incubated at 60 ° C, and the reaction produced alcohol was removed during the reaction and the reaction was carried out for about 6 hours. The temperature is raised to the reflux reaction until the raw material disappears. N-methylpiperazine was completely substituted and N-methylpiperazine was recovered under reduced pressure. After acid, alkali pH adjustment, by extraction, washing, concentration and other steps. Finally, the concentrated solid was recrystallized from methanol, filtered and the mother liquor was concentrated and separated on a silica gel column (mobile phase methanol: dichloromethane = 1: 8). The solid was combined to give the ofloxacin product 3.44 g yeleld 95.8percent. Compounds were determined by melting point, high molecular mass spectrometry, molecular weight, and nuclear magnetic resonance spectroscopy. The product was the same product as the product obtained in Example 7 and was anloxacin product.General procedure: A mixture of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid 1a (1 mmol) and Nethylpiperazine2y (1.5 mmol) and n-FZSA (0.06 g) as catalystin H2O (5 ml) were heated under reflux for the appropriatetime. The reaction was monitored by TLC. After appropriatetime, the catalyst was separated using an externalmagnet and washed with hot ethanol (5 mL). The reactionmixture was then cooled to room temperature. The precipitatedsolid was collected by filtration, and recrystallized fromethanol 96percent to give desired compound in high yields.General procedure: A mixture of 6-chloro-4-cyclopropyl-7-fluoro-1-oxo-1, 4-dihydronaphthalene-2-carboxylic acid 1a (1 g, 3.5 mmol) with N-ethylpiperazine 2c (0.6 g, 5.25mmol) was loaded in a small flask fitted with a micro condenser, placed in the microwave reactor and irradiated for 25 min at 150°C under solvent free conditions. The reaction progress was monitored by TLC. Upon completion of the process, addition of hot absolute ethanol (10 mL) to the reaction mixture was followed by filtration. The filtrate was concentrated and stored at room temperature for precipitation. The solid was filtered off and recrystallized from absolute ethanol to give compound 3c.20 g of 9, 10-difluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido[1, 2, 3-de]-1, 4-benzoxazine-6-carboxylic acid ethyl ester, Sixty grams of N-methylpiperazine was charged to 250 ml and equipped with refluxThe reaction flask was charged with 20 g of N, N-dimethylformamide and 15 g of water, incubated at 105 ° C for about 8 hours, N-methylpiperazine to be replaced completely, the solvent was evaporated to dryness under reduced pressure, Add 80 grams of water dissolved, then add acetic acid 7.4 grams, Heated to 70 ° C , stirred for 2 hours, after acid, Alkaline pH adjustment, by extraction, washing, concentration, Crystallization and other steps, had 21.05 grams of ofloxacin finished product, The molar yield was 87.9percent.

Fluorinated quinolone antibacterial The third-generation quinolones synthetic antibacterial drugs have the advantages of broad antibacterial spectrum, strong antibacterial activity, good bioavailability, safe and effective oral administration, low toxicity, and no drug resistance. It has good antibacterial effects on a variety of Gram-positive and Gram-negative bacteria, and also has antibacterial effects on Pseudomonas aeruginosa and Chlamydia. For strains resistant to neopenicillin, clindamycin, gentamicin and strains resistant to norfloxacin, this product works well without cross-resistance. In addition, it also has a certain antibacterial effect on anaerobic bacteria. It is used for respiratory infections, intestinal infections, skin and soft tissue infections, urinary system infections caused by sensitive bacteria.

Molecular Weight:361.4
XLogP3:-0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:2
Exact Mass:361.14378429
Monoisotopic Mass:361.14378429
Topological Polar Surface Area:73.3
Heavy Atom Count:26
Complexity:634
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes