163680-77-1 Usage
Description
Pazufloxacin mesilate, also known as a fluoroquinolone antibiotic, is a broad-spectrum synthetic compound co-developed by Toyama and Mitsubishi Pharm. It is a crystalline solid that exhibits potent activity against both Gram-negative and Gram-positive bacteria, including various clinical isolates. Its mechanism of action involves the inhibition of bacterial DNA gyrase and topoisomerase IV, thereby disrupting bacterial DNA replication and transcription.
Uses
Used in Pharmaceutical Industry:
Pazufloxacin mesilate is used as an intravenous antibiotic for the treatment of various types of infections, such as respiratory, urinary, surgical, gynecological, and systemic infections. Its broad-spectrum activity and effectiveness against both Gram-negative and Gram-positive bacteria make it a valuable asset in managing a wide range of bacterial infections.
Used in Antimicrobial Therapy:
Pazufloxacin mesilate is utilized as an antimicrobial agent to combat infections caused by antibiotic-resistant strains, such as methicillin-resistant S. aureus (MRSA) and methicillin-resistant S. epidermidis (MRSE). Its ability to inhibit key bacterial enzymes, like DNA gyrase and topoisomerase IV, contributes to its efficacy in treating these resistant infections.
Used in Research and Development:
Pazufloxacin mesilate serves as a valuable compound in the ongoing research and development of new antibiotics and antimicrobial agents. Its unique properties and broad-spectrum activity provide a foundation for the design and synthesis of novel compounds with improved efficacy and reduced resistance potential.
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 bromide
and then with t-butyl cyanoacetate in the presence of
potassium carbonate in DMSO in one flask to give acylated
cyanoacetate 169. Intermediate 169 thus obtained without
purification was refluxed in toluene with p-TSA to yield 4-
cyanomethylbenzoate 170 in 90% yield from 168.
Cyclopropanation at the benzylic position of 170 was
performed by α,α-dialkylation with two equiv. of 1,2-
dibromoethane under phase-transfer conditions to give
cyanocyclopropyl compound 171. Cyano compound 171
was subjected to hydration with alkaline H2O2 to afford
carboxamide 172 in 81% yield from 170. Subsequently,
carboxamide 172 was treated with NaOCl for Hofmann
rearrangement to give primary amine 173, which was
protected as its N-acetyl derivative 174 for the next reaction.
Treatment of 174 with imidazole in the presence of thionyl
chloride and TEA generated an imidazolide intermediate,
which was converted to β-keto ester 175 by reacting with
potassium ethyl malonate and MgCl2. Enamine 176 was
obtained without purification by successive treatment of 175
with DMF-dimethylacetal and (S)-(+)-2-aminopropanol.
Crude 176 was heated in DMSO in the presence of
potassium carbonate to efficiently give tricycle product 177
in 80% yield from 174. Finally, the ethyl ester and acetamide in 177 were hydrolyzed under basic and acidic
conditions, respectively, to give the free amine. Pazufloxacin
mesilate (20) was obtained in 94% yield by treatment of its
corresponding free amine with methanesulfonic acid in
ethanol.
Check Digit Verification of cas no
The CAS Registry Mumber 163680-77-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,3,6,8 and 0 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 163680-77:
(8*1)+(7*6)+(6*3)+(5*6)+(4*8)+(3*0)+(2*7)+(1*7)=151
151 % 10 = 1
So 163680-77-1 is a valid CAS Registry Number.
InChI:InChI=1/C16H15FN2O4.CH4O3S/c1-7-6-23-14-11(16(18)2-3-16)10(17)4-8-12(14)19(7)5-9(13(8)20)15(21)22;1-5(2,3)4/h4-5,7H,2-3,6,18H2,1H3,(H,21,22);1H3,(H,2,3,4)/t7-;/m0./s1
