Abstract
Hydroxyquinoline 1 reacts with ethyl chloroacetate in the presence of anhydrous K2CO3 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)}acetohydrazides 5a-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.
Highlights
The importance of the quinoline nucleus has been well demonstarted as illustrated by the large number of patents employing such species as chemotherapeutic agents
A number of biological activities have been associated with quinoline-containing compounds such as anti-inflammatory, antiallergic[1], antimalarial[2], antibacterial[3], antiproliferative[4], anticancer[5,6] and antiparasitic[6] activities
We have synthesized a new class of combinational molecules in which all of these moieties are present
Summary
Abstract 8-Hydroxyquinoline 1 reacts with ethyl chloroacetate in the presence of anhydrous K2CO3 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)}acetohydrazides 5a-e. These, on cyclization with mercaptosuccinic acid, yield (2-aryl-4-oxo-3-{[(quinolin-8-yloxy)acetyl]amino}-1,3-thiazolidin5-yl) acetic acids 6a-e. Compounds 6a-e are further converted into acid chloride derivatives 7ae 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
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
