Synthesis and antimicrobial activity of succinimido(2-aryl-4-oxo-3-{[(quinolin-8-yloxy)acetyl]amino}-1,3-thiazolidin-5-yl)acetates

Abstract

8-Hydroxyquinoline 1 reacts with ethyl chloroacetate in the presence of anhydrous K 2 CO 3 to produce ethyl (quinolin-8-yloxy)acetate 2. Treatment of 2 with hydrazine hydrate forms 2-(quinolin-8-yloxy)acetohydrazide 3, which on condensation with various aldehydes 4a-e gives N'-{[(1Z)-arylmethylene]-2-(quinolin-8-yloxy)}acetohydrazides5a-e. These, on cyclization with mercaptosuccinic acid, yield (2-aryl-4-oxo-3-{[(quinolin-8-yloxy)acetyl]amino}-1,3-thiazolidin-5-yl) acetic acids 6a-e. Compounds 6a-e are further converted into acid chloride derivatives 7a-e by reaction with thionyl chloride. Subsequent treatment of 7a-e with N-hydroxysuccinimide in the presence of TEA furnishes the title compounds 8a-e. Antibacterial and antifungal activities of the final compounds have been evaluated and all the compounds have shown significant inhibition of bacterial and fungal growth.

A Retrievable and Highly Selective Fluorescent Probe for Monitoring Sulfide and Imaging in Living Cells

“…Preparation of (E)-2-[6-Hydroxy-3-oxo-5-[ [2-[2-(quinolin-8yloxy)acetyl]hydrazono]methyl]-3H-xanthen-9-yl]benzoic Acid (L1). 2-(5-Formyl-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid 21 (1) and 2-(quinolin-8-yloxy)acetohydrazide (2) 22 were prepared by the reported method. Compound 1 (180 mg, 0.5 mmol) was dissolved in 25 mL of ethanol, followed by the addition of compound 2 (130 mg, 0.6 mmol).…”

“…2-(5-Formyl-6-hydroxy-3-oxo-3 H -xanthen-9-yl)­benzoic acid ( 1 ) and 2-(quinolin-8-yloxy)­acetohydrazide ( 2 ) were prepared by the reported method. Compound 1 (180 mg, 0.5 mmol) was dissolved in 25 mL of ethanol, followed by the addition of compound 2 (130 mg, 0.6 mmol).…”

A Simple Procedure for Synthesis of Biological Active 4-oxo-4-(quinolin-8-yloxy)but-2-enoic acid

“…In research [8], antibacterial and antifungal activities of succinimido(2-aryl-4-oxo-3-{[(quinolin-8-yloxy)acetyl]amino}-1,3-thiazolidin-5-yl) acetates (12a-e) have been evaluated. All the compounds have shown significant inhibition of bacte-rial and fungal growth as compared to the standard (amicacin).…”

“…All the compounds have shown significant inhibition of bacte-rial and fungal growth as compared to the standard (amicacin). Among them, compound (12b) is highly active against Staphylococcus aureus, Staphylococcus albus, Streptococcus faecalis, Klebsiella pneumonia and Pseudomonas aeuroginosa [8].…”

A Three-Component Reaction between Azaarenes (Phenanthridine, Quinoline or Isoquinoline), Acetylenic Esters and Phenol Derivatives

“…11 A number of biological activities have been associated with quinoline-containing compounds such as anti-flammatory, antimalarial, antibacterial, anticancer and antiparasitic. 12,13 Substituted phenanthridines are an important class of heterocyclic compounds in material science 14 and in medicinal chemistry due to their significant biological activities, [15][16][17] including antifungal, antimicrobial and antiinflammatory. 18 I now describe the reaction between azaarenes (phenanthridine, quinoline and isoquinoline) and acetylenic esters in the presence of phenol derivatives (see Scheme 1 and Table 1).…”