163253-35-8 Usage
Description
Sitafloxacin, also known as sitafloxacin hydrate, is a new-generation, broad-spectrum oral fluoroquinolone antibiotic developed by Daiichi Sankyo. It is characterized by its off-white solid appearance and was approved and launched in Japan. Sitafloxacin exhibits potent antibacterial activity against a wide range of Gram-positive, Gram-negative, and anaerobic clinical isolates, including strains resistant to other fluoroquinolones. Its mode of action involves the inhibition of DNA gyrase and topoisomerase IV, making it a promising pharmaceutical candidate for various applications in the treatment of bacterial infections.
Uses
Used in Pharmaceutical Industry:
Sitafloxacin is used as an antibacterial agent for the treatment of various inflammatory infections. These include laryngopharyngitis, adenoiditis, acute bronchitis, pneumonia, secondary infections due to chronic respiratory lesions, cystitis, pyelonephritis, urethritis, cervicitis, otitis media, sinusitis, periodontitis, pericoronitis, and jaw inflammation. Its broad spectrum of potent antibacterial activity makes sitafloxacin a valuable asset in treating severe cases of bacterial infection, relapse/recrudescence of infection, and infections where resistant bacteria are suspected to be the cause.
Synthesis
The optically pure fluorocyclopropylamine 111 intermediate
was prepared as described in thescheme. Condensation of
diphenylmethyl amine 104 with acetaldehyde followed by
treatment with trichloromethyl chloroformate in the presence
of triethylamine gave N-vinyl carbamoyl chloride 105 in
53% yield. This intermediate was reacted with sodium benzyloxide
(generated in situ) to afford N-vinylcarbamate 106
in 82% yield. Fluorocyclopropanation of 106 with zinc–
monofluorocarbenoid generated from fluorodiiodomethane
and diethylzinc provided N-(2-fluorocyclopropyl)carbamate
107 in 90% yield and with a diastereomeric ratio of 93:7
favoring the cis-isomer. Hydrogenolysis of the CBz and the
diphenylmethyl groups was accomplished with catalytic 10%
palladium on charcoal and was followed by treatment with
TsOH to afford dl-108 as its tosylate salt. Acylation of dl-
108 TsOH with l-menthyl chloroformate gave a 1:1 mixture
of the diastereomeric carbamate 109 which upon four repeated
recrystallizations from hexane/ethyl acetate afforded
optically pure 110 in 26% yield. Acidic hydrolysis of 110
furnished 111 as its HCl salt in 88% yield.
Check Digit Verification of cas no
The CAS Registry Mumber 163253-35-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,3,2,5 and 3 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 163253-35:
(8*1)+(7*6)+(6*3)+(5*2)+(4*5)+(3*3)+(2*3)+(1*5)=118
118 % 10 = 8
So 163253-35-8 is a valid CAS Registry Number.
InChI:InChI=1/C19H18ClF2N3O3.H2O/c20-14-15-8(17(26)9(18(27)28)5-25(15)12-4-10(12)21)3-11(22)16(14)24-6-13(23)19(7-24)1-2-19;/h3,5,10,12-13H,1-2,4,6-7,23H2,(H,27,28);1H2/t10-,12?,13+;/m0./s1
