Prulifloxacin

Base Information

• Chemical Name: Prulifloxacin
• CAS No.: 123447-62-1
• Molecular Formula: C21H20FN3O6S
• Molecular Weight: 461.471
• Mol file: 123447-62-1.mol

Synonyms:1H,4H-[1,3]Thiazeto[3,2-a]quinoline-3-carboxylic acid,6-fluoro-1-methyl-7-[4-[(5-methyl- 2-oxo-1,3-dioxol-4-yl)methyl]-1- piperazinyl]-4-oxo-;PUFX;(+-)-7-(4-((Z)-2,3-Dihydroxy-2-butenyl)-1-piperazinyl)-6-fluoro-1-methyl-4-oxo-1H,4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylic acid, cyclic carbonate;Sword;Sword (TN);

Chemical Property of Prulifloxacin

Chemical Property:

• Appearance/Colour: Yellow or slightly yellow power
• Vapor Pressure: 1.77E-20mmHg at 25°C
• Melting Point: 211-214°C
• Refractive Index: 1.698
• Boiling Point: 633.2 °C at 760 mmHg
• PKA: 5.85±0.40(Predicted)
• Flash Point: 336.8 °C
• PSA: 134.43000
• Density: 1.62 g/cm³
• LogP: 2.64270
• Storage Temp.: -20°C Freezer
• Solubility.: 1 M NaOH: soluble25ML, clear, colorless (Solvent: 1 mg + 25 mL o
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 461.10568470
• Heavy Atom Count: 32
• Complexity: 925

Purity/Quality:

99% ^*data from raw suppliers

Prulifloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1N2C3=CC(=C(C=C3C(=O)C(=C2S1)C(=O)[O-])F)N4CC[NH+](CC4)CC5=C(OC(=O)O5)C
• Description: Prulifloxacin was launched as the third fluoroquinone. It was introduced in Japan as an oral treatment for urinary tract infections (UTls), respiratory tract infections (RTls) and bacterial pneumoniae. It can be synthesized in 10 steps from commercially available 3,4-difluoroaniline. Key steps involve the cyclization of 6,7-difluoro-rl-hydroxy-2- thioquinoline-3carboxylic acid ethyl ester with 1 ,I-dibromomethane to give the corresponding thiazeto-[3,2a]quinoline. Aromatic nucleophilic substitution of the 7-fluoro atom with piperazine followed by hydrolysis of the ethyl ester and finally alkylation of the piperazinyl moiety with 4-(bromomethyl)-5-methyl-l ,bdioxol-Bone complete the synthesis. Prulifloxacin is a lipophilic prodrug, which is rapidly hydrolyzed to the corresponding Ndealkylated piperazine, NM 394, by paraoxonase type enzymes in blood and liver following intestinal absorption. The DNA gyrase inhibitor NM 394 accounts for all antimicrobial activity: it shows a similar or greater activity against gram-positive bacteria compared to ciprofloxacin, and a greater activity in the case of gram-negative bacteria. In clinical studies, prulifloxacin has shown good efficacy against UTls and RTls. The drug is mainly excreted in the urine and in the feces as unchanged NM 394, which has a plasma half-life of approximately 8 h. Phototoxicity in animal models is less severe than with other quinolones. Prulifloxacin is well tolerated with an adverse effect profile similar to that of other fluoroquinolones.
• Uses: Fluoroquinoline antibacterial; prodrug for active metabolite, Ulifloxacin. Antibacterial. Prulifloxacin Polymorph I is a crystallization form of a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class. Prulifloxacin is a prodrug for active metabolite, Ulifloxacin. Antibacterial. Prulifloxacin is a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class. Prulifloxacin is a prodrug for active metabolite, Ulifloxacin. Antibacterial.

Technology Process of Prulifloxacin

There total 19 articles about Prulifloxacin 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: 95.4%

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one (80715-22-6) + ulifloxacin (112984-60-8) → prulifloxacin (123447-62-1)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 ℃; for 5h; Large scale;

Reference yield:

6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid hydrochloride (123447-63-2) → prulifloxacin (123447-62-1)

Guidance literature:

With triethylamine; In methanol; dichloromethane; at 0 - 5 ℃; for 1.5h; Product distribution / selectivity;

Reference yield:

ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate (113028-17-4) → prulifloxacin (123447-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / KOH / 2-methyl-propan-2-ol; H₂O / 1 h / 50 - 60 °C

2: 62 percent / KHCO₃ / dimethylformamide / 5 h / Ambient temperature

With potassium hydroxide; potassium hydrogencarbonate; In water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm00103a011

upstream raw materials:

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one

ulifloxacin

4-chloromethyl-5-methyl-1,3-dioxol-2-one

3,4-difluorophenyl isothiocyanate

Refernces

• 1、 -. "A method for preparing of plurichari (by machine translation)". Paragraph 0044; 0058; 0059; 0060. . Retrieved 2016/10/07.
• 2、 -. "PROCESS FOR THE PREPARATION OF HIGHLY PURE PRULIFLOXACIN". Page/Page column 17. . Retrieved 2009/09/05.