Microwave Assisted Stereoselective Synthesis and Antibacterial Activity of New Fluoroquinolinyl-β-lactam Derivatives

Abstract

A series of quinoline ring substituted N-(3-chloro-2-(2-¯uoro-quinolin-3-yl)-4-oxoazetidin-1-yl)-octanamides were synthesized from chloroacetyl chloride, octanoic acid, (2-¯uoro-quinolin-3-yl-methylene)-hydrazides, and triethylamine using microwave irradiation as well as conventional heating. The reaction time can be brought down from hours to minutes with improved yields using microwave irradiation compared to conventional heating. The compounds were tested for their in vitro antibacterial activity against 2253-Corynebacterium rubrum, 2340-Enterobacter, 2491-Erwinia herbicola, K 12 -E. coli, and 2873-Z. mobilis. and found to possess activities comparable with or superior to the standard drug ampicillin.

Quinoline Hydrazide/Hydrazone Derivatives: Recent Insights on Antibacterial Activity and Mechanism of Action

“…SAR study deduce that the substitution by β-lactam moiety in the 3 rd position of 2-fluoro quinoline increased the antibacterial potency. [87] In general, the aforementioned study concluded that hydrazide/hydrazone substitution at the 3 rd position of quinoline ring enhanced the antibacterial activity with huge potential as compared to substitution at the 1 st and 2 nd positions of quinoline ring. In many cases, these compounds showed equipotent activity as standard drugs.…”

“…Amongst the studied compounds, 30 was the most potent compound (ZOI=21 mm) and showed significant activity in comparison to standard drug ampicillin (ZOI=16 mm) against 2340‐ Enterobacte r. Compound 30 also showed standard drug equivalent activity against 2491 ‐Erwinia herbicola (ZOI=21 mm). SAR study deduce that the substitution by β ‐lactam moiety in the 3 rd position of 2‐fluoro quinoline increased the antibacterial potency [87] …”

Microwave Induced Synthesis and Antibacterial Activity of Cephalosporin Derivatives Using Solid Support

“…Currently the use of microwave energy to accelerate organic reactions has been taken to a new dimension, is a matter of increasing interest and offers several advantages (10,11). Moreover the coupling of MWI with the use of inexpensive inorganic solid supported reagents (12,13) is consider as efficient, ecofriendly technology.…”

Microwave assisted efficient one-pot synthesis of 3,5,6-trisubstituted-1,2,4-triazines from fatty acid hydrazides under solvent-free conditions and their antimicrobial activity

“…1 The use of microwave irradiation is an established tool in organic synthesis for achieving better selectivity, rate enhancement and reduction of thermal degradation byproducts. 2,3 However these procedures are practically limited as solvents in a microwave oven at elevated temperatures create high pressure, which may cause explosion. One of the advances to overcome this problem is inorganic 4,5 solid supported organic synthesis which attracts attention because of enhanced selectivity, milder reaction conditions and associated ease of manipulation.…”