Introduction：Basic information about Pazufloxacin mesilate CAS 163680-77-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Pazufloxacin mesilate Basic information
| Product Name: | Pazufloxacin mesilate |
| Synonyms: | (3S)-10-(1-AMinocyclopropyl)-9-fluror-2,3-dihydro-3-Methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid Methanesulfonate;Mesylate pazufloxacin;T 3762;PASIL;PAZUCROSS;PAZUFLOXACIN MESILATE;PAZUFLOXACIN MESYLATE;PAZUFLOXACIN METHANESULFONATE |
| CAS: | 163680-77-1 |
| MF: | C17H19FN2O7S |
| MW: | 414.4053632 |
| EINECS: | 634-946-6 |
| Product Categories: | PAZUCROSS;Aromatics;Chiral Reagents;API;Intermediates & Fine Chemicals;Pharmaceuticals;Amines |
| Mol File: | 163680-77-1.mol |
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Pazufloxacin mesilate Chemical Properties
| Melting point | >255°C (dec.) |
| alpha | D20 -64.2° (c = 1 in 1.0N NaOH) |
| storage temp. | -20°C Freezer |
| solubility | Aqueous Base (Slightly), DMSO (Slightly) |
| form | Solid |
| color | Off-White to Pale Yellow |
| InChIKey | UDHGFPATQWQARM-FJXQXJEOSA-N |
| SMILES | S(C([H])([H])[H])(=O)(=O)O[H].FC1C([H])=C2C(C(C(=O)O[H])=C([H])N3[C@@]([H])(C([H])([H])[H])C([H])([H])OC(=C32)C=1C1(C([H])([H])C1([H])[H])N([H])[H])=O |
| CAS DataBase Reference | 163680-77-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi,C,F |
| Risk Statements | 36/37/38-34-11 |
| Safety Statements | 26-45-36/37/39-16 |
| RTECS | UU8815400 |
| HS Code | 29349990 |
Pazufloxacin mesilate Usage And Synthesis
| Description | This fluoroquinolone was co-developed by Toyama andMitsubishi Pharm and was launched for the intravenoustherapy of respiratory, urinary, surgical, gynecological andsystemic infections. |
| Description | Pazufloxacin is a broad-spectrum synthetic fluoroquinolone antibiotic. It is active against Gram-negative and Gram-positive bacteria, including clinical isolates of E. coli, K. pneumoniae, methicillin-susceptible and -resistant S. aureus, and methicillin-susceptible and -resistant S. epidermidis (MIC90s = 0.05, 0.1, 0.39, 12.5, 0.39, and 6.25 μg/ml, respectively). It inhibits E. coli, P. aeruginosa, and S. aureus DNA gyrase (IC50s = 0.88, 1.9, and 10.2 μg/ml, respectively) and S. aureus topoisomerase IV (IC50 = 24.2 μg/ml) in cell-free assays. In vivo, pazufloxacin is active against systemic E. coli, K. pneumoniae, and methicillin-resistant S. aureus infections in mice (ED50s = 0.15, 5.5, and 4.5 mg/kg, respectively). |
| Chemical Properties | Crystalline Solid |
| Uses | A fluorinated quinolone antibiotic. Antibacterial. |
| Synthesis | Pazufloxacin Mesilate is elegantly synthesized from commercially available 2,3,4,5-tetrafluorobenzoic acid(168) by an 11-step process with an overall yield 48% [68].Starting material 168 was first treated with ethyl bromideand then with t-butyl cyanoacetate in the presence ofpotassium carbonate in DMSO in one flask to give acylatedcyanoacetate 169. Intermediate 169 thus obtained withoutpurification was refluxed in toluene with p-TSA to yield 4-cyanomethylbenzoate 170 in 90% yield from 168.Cyclopropanation at the benzylic position of 170 wasperformed by |á,|á-dialkylation with two equiv. of 1,2-dibromoethane under phase-transfer conditions to givecyanocyclopropyl compound 171. Cyano compound 171was subjected to hydration with alkaline H2O2 to affordcarboxamide 172 in 81% yield from 170. Subsequently,carboxamide 172 was treated with NaOCl for Hofmannrearrangement to give primary amine 173, which wasprotected as its N-acetyl derivative 174 for the next reaction.Treatment of 174 with imidazole in the presence of thionylchloride and TEA generated an imidazolide intermediate,which was converted to |?-keto ester 175 by reacting withpotassium ethyl malonate and MgCl2. Enamine 176 wasobtained without purification by successive treatment of 175with DMF-dimethylacetal and (S)-(+)-2-aminopropanol.Crude 176 was heated in DMSO in the presence ofpotassium carbonate to efficiently give tricycle product 177in 80% yield from 174. Finally, the ethyl ester and acetamide in 177 were hydrolyzed under basic and acidicconditions, respectively, to give the free amine. Pazufloxacinmesilate (20) was obtained in 94% yield by treatment of itscorresponding free amine with methanesulfonic acid inethanol. |
| References | [1] T MURATANI S M M Inoue. In vitro activity of T-3761, a new fluoroquinolone.[J]. Antimicrobial Agents and Chemotherapy, 1992, 36 10: 2293-2303. DOI: 10.1128/aac.36.10.2293
[2] Y FUKUOKA. In vitro and in vivo antibacterial activities of T-3761, a new quinolone derivative.[J]. Antimicrobial Agents and Chemotherapy, 1993, 37 3: 384-392. DOI: 10.1128/aac.37.3.384 |
Pazufloxacin mesilate Preparation Products And Raw materials
