7-Fluoro-2-methyl-6-(4-methylpiperazin-4-ium-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate

Base Information

• Chemical Name: 7-Fluoro-2-methyl-6-(4-methylpiperazin-4-ium-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate
• CAS No.: 82419-36-1
• Molecular Formula: C18H20FN3O4
• Molecular Weight: 361.373
• Hs Code.: 29349990
• Mol file: 82419-36-1.mol

Synonyms:7-Fluoro-2-methyl-6-(4-methylpiperazin-4-ium-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate;STL047996;AKOS005701543;9-fluoro-3-methyl-10-(4-methylpiperazin-4-ium-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate

Chemical Property of 7-Fluoro-2-methyl-6-(4-methylpiperazin-4-ium-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 6.7E-14mmHg at 25°C
• Melting Point: 270-275 °C
• Refractive Index: 1.669
• Boiling Point: 571.5 °C at 760 mmHg
• PKA: 5.19±0.40(Predicted)
• Flash Point: 299.4 °C
• PSA: 75.01000
• Density: 1.48 g/cm³
• LogP: 1.54690
• Storage Temp.: 2-8°C
• Solubility.: 1 M NaOH: soluble50mg/mL
• Water Solubility.: Soluble in acetic acid or water. Slightly soluble in methanol
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 361.14378429
• Heavy Atom Count: 26
• Complexity: 628

Purity/Quality:

99% ^*data from raw suppliers

Ofloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-42/43-68-36/37/38
• Safety Statements: 26-36/37/39-24/25-22-37/39-60

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CC[NH+](CC4)C)F)C(=O)[O-]
• Description: Ofloxacin is an antibacterial agent with increased potency in comparison to the prototype third generation quinolone, norfloxacin. It has a broad spectrum of activity against gram-positive and gram-negative bacteria and is useful in the treatment of kidney, genitourinary, and upper respiratory tract infections. Ofloxacin is a broad-spectrum fluoroquinolone antibiotic that prevents supercoiling of bacterial chromosomes by DNA gyrase. It is active against Gram-positive and Gram-negative bacteria with MIC90s ranging from 0.39 to 3.13 μg/ml for clinical isolates of S. aureus, S. epidermidis, S. pyogenes, and S. faecalis and ≤0.78 μg/ml for N. gonorrhoeae and various species of Enterobacteriaceae. Ofloxacin is active in vivo, with ED50 values ranging from 0.7 to 75.1 mg/kg in infected mice. Formulations containing ofloxacin have been used to treat urinary tract infections, gonorrhea, prostatitis, and gastroenteritis.
• Uses: Fluorinated quinolone antibacterial Ofloxacin is a fluorinated quinolone antibacterial.This compound is a contaminant of emerging concern (CECs).
• Indications: Ofloxacin also possesses a broad spectrum of antimicrobial action. It is highly active with respect to Gram-negative microorganisms, such as blue-pus bacillus, hemophilic and colon bacillus, shigella, salmonella, and chlamydia. It is used for infections of the respiratory tract, ears, throat, nose, skin, soft tissue, bones, joints, infective-inflammatory diseases of the abdominal cavity organs (kidneys, urinary tract), and organs of the pelvis minor (genitalia), and for gonorrhea. Synonyms of this drug are tarivid, flobacin, and others.
• Therapeutic Function: Antibacterial
• Clinical Use: 9-Fluoro-2,3-dihydro-3-methyl-10(4-methyl-1-piperazin-yl)-7-oxo-7H-pyrido[1,2,3-de]-1,4,-benzoxazine-6-carboxylicacid (Floxin, Floxin IV) is a member of the quinolone class of antibacterial drugs wherein the 1- and 8-positions are joined in the form of a 1,4-oxazine ring.Ofloxacin has been approved for the treatment of infectionsof the lower respiratory tract, including chronic bronchitisand pneumonia, caused by Gram-negative bacilli. It isalso used for the treatment of pelvic inflammatory diseaseand is highly active against both gonococci and chlamydia.In common with other fluoroquinolones, ofloxacin is not effectivein the treatment of syphilis. A single 400-mg oraldose of ofloxacin in combination with the tetracycline antibioticdoxycycline is recommended by the Centers forDisease Control and Prevention (CDC) for the outpatienttreatment of acute gonococcal urethritis. Ofloxacin is alsoused for the treatment of urinary tract infections caused byGram-negative bacilli and for prostatitis caused by E. coli.Infections of the skin and soft tissues caused by staphylococci,streptococci, and Gram-negative bacilli may also betreated with ofloxacin. Complicated and uncomplicated infections of the urinary tract, chronic prostatitis Uncomplicated urogenital and anorectal gonorrhea (single-dose), chancroid (3-day course), genital chlamydial infections (7-day course) Lower respiratory tract infections, including bronchopneumonia, community-acquired pneumonia (except pneumococcal pneumonia), acute bacterial exacerbations of chronic bronchitis (unless pneumococci are involved) and bronchiectasis Enteric fever, including the chronic carrier state; gastroenteritis caused by enterotoxigenic Escherichia coli, Salmonella, Shigella and Campylobacter spp. Ocular infections (ophthalmic preparation)
• Drug interactions: Potentially hazardous interactions with other drugs Aminophylline: possibly increased risk of convulsions, increased levels of aminophylline. Analgesics: increased risk of convulsions with NSAIDs. Anticoagulants: anticoagulant effect of coumarins enhanced. Antimalarials: manufacturer of artemether with lumefantrine advises avoid. Ciclosporin: increased risk of nephrotoxicity. Theophylline: possibly increased risk of convulsions.

Technology Process of 7-Fluoro-2-methyl-6-(4-methylpiperazin-4-ium-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate

There total 27 articles about 7-Fluoro-2-methyl-6-(4-methylpiperazin-4-ium-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.8%

1-methyl-piperazine (109-01-3) + 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid (82419-35-0) → ofloxacin (82419-36-1,83380-47-6)

Guidance literature:

With potassium hydroxide; In water; at 60 ℃; for 6h; Time; Solvent;

Reference yield: 87.9%

1-methyl-piperazine (109-01-3) + ethyl 9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate (82419-34-9) → ofloxacin (82419-36-1,83380-47-6)

Guidance literature:

With acetic acid; In water; N,N-dimethyl-formamide; at 70 - 105 ℃; for 10h; Temperature; Reagent/catalyst; Solvent;

Reference yield:

1-methyl-piperazine (109-01-3) + C17H14BF2NO8 → ofloxacin (82419-36-1,83380-47-6)

Guidance literature:

1-methyl-piperazine; C₁₇H₁₄BF₂NO₈; With triethylamine; In dichloromethane; at 40 ℃; for 1.5h; Inert atmosphere;

With hydrogenchloride; In methanol; water; at 0 - 30 ℃; for 3h;

upstream raw materials:

1-methyl-piperazine

9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid

8-Fluoro-3-methyl-9-(4-methyl-piperazin-1-yl)-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid acetoxymethyl ester

8-Fluoro-3-methyl-9-(4-methyl-piperazin-1-yl)-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid 1-acetoxy-ethyl ester

Downstream raw materials:

9-fluoro-2,3-dihydro-3-methyl-10-(N-methyl-N',N-diformyl-2-aminoethylamino)-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid

levofloxacin

(R)-ofloxacin

4-[6-carboxy-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazin-10-yl]-1-methylpiperazine 1-oxide

Refernces

Design, synthesis, molecular docking, antimicrobial, and antioxidant activities of new phenylsulfamoyl carboxylic acids of pharmacological interest

10.1007/s00044-019-02440-3

This research endeavored to synthesize and evaluate new phenylsulfamoyl carboxylic acids for their antimicrobial, antioxidant, and molecular docking properties. The study aimed to develop compounds with potent pharmacological activities and to assess their efficacy against various microorganisms and oxidative stress conditions. The synthesis involved the reaction of amino acids with benzenesulfonyl chloride in an aqueous base medium, yielding compounds 4a–4g. These compounds were then characterized using various analytical techniques and tested for their biological activities. The results indicated that compounds 4c, 4d, 4e, and 4g exhibited superior in vitro antibacterial and antifungal activities compared to the standard drug Ofloxacin, while compound 4e showed the most excellent antioxidant activity. Molecular docking studies revealed that these compounds had significant interactions with various disease-related targets, suggesting their potential as effective antibacterial, antifungal, antioxidant, antitrypanosome, and antimalaria agents. The research concluded that the synthesized phenylsulfamoyl carboxylic acids hold promise as potent agents in medicinal chemistry.