Abstract
Following our previous studies, to affiliate selective pharmacophore in a single molecular entity, domino, ecologically benign, four hetero-component, single pot reaction has been carried out in (bmim)BF4 ionic liquid to structure a new class of compact heteronuclei. In a newly constructed heterocyclic Ugi adducts, quinoline was used as nitrogen source and benzothiazole as well as thiophene moieties were selected to introduce sulphur functionality. This Ugi eco-compatible heterocyclic synthesis resulted in relatively good yields with prompt reaction time. New products were screened for their in vitro antimicrobial activity against a representative panel of bacteria and fungi and some of the final analogues displayed more or equal potency at MIC range 6.25-25 µg/mL than control drugs ampicillin, gentamicin and fluconazole (MICs: 6.25-25 µg/mL). The structural assignments of the new products were done on the basis of FT-IR, 1H NMR spectroscopy and elemental analysis.
Keywords: Thiophehe, Furan, Quinoline, Coumarin, Benzothiazole, Ugi reaction, Antimicrobial activity.
Current Organic Chemistry
Title:Ionic Liquid Mediated Tandem Synthesis of Bioactive Quinoline Based Thiophene/ Thiazole Linked Multi-Heterocomponent Ugi Adducts
Volume: 17 Issue: 10
Author(s): Rahul V. Patel, Kishor H. Chikhalia, Shivraj H. Nile and Se Won Park
Affiliation:
Keywords: Thiophehe, Furan, Quinoline, Coumarin, Benzothiazole, Ugi reaction, Antimicrobial activity.
Abstract: Following our previous studies, to affiliate selective pharmacophore in a single molecular entity, domino, ecologically benign, four hetero-component, single pot reaction has been carried out in (bmim)BF4 ionic liquid to structure a new class of compact heteronuclei. In a newly constructed heterocyclic Ugi adducts, quinoline was used as nitrogen source and benzothiazole as well as thiophene moieties were selected to introduce sulphur functionality. This Ugi eco-compatible heterocyclic synthesis resulted in relatively good yields with prompt reaction time. New products were screened for their in vitro antimicrobial activity against a representative panel of bacteria and fungi and some of the final analogues displayed more or equal potency at MIC range 6.25-25 µg/mL than control drugs ampicillin, gentamicin and fluconazole (MICs: 6.25-25 µg/mL). The structural assignments of the new products were done on the basis of FT-IR, 1H NMR spectroscopy and elemental analysis.
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Cite this article as:
Patel Rahul V., Chikhalia Kishor H., Nile Shivraj H. and Park Se Won, Ionic Liquid Mediated Tandem Synthesis of Bioactive Quinoline Based Thiophene/ Thiazole Linked Multi-Heterocomponent Ugi Adducts, Current Organic Chemistry 2013; 17 (10) . https://dx.doi.org/10.2174/1385272811317100013
DOI https://dx.doi.org/10.2174/1385272811317100013 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Chemistry and Biology of Carbohydrates
Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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