Abstract
A series of 7-heteroaryl-4-oxo-4,7-dihydrothieno[2,3-b]-pyridine-5-carboxylic acids (8a-d) and their methyl esters (7a-d) were prepared by cyclization of the respective 2-(2,5-dichlorothien-3-yl)-3-(N-heteroarylamino)acrylates (6a-d). The latter are accessible from methyl 2-(2,5-dichlorothien-3-yl)-3-ethoxyacrylate (5) which is obtained via methyl 3-(2,5-dichlorothien-3-yl)-3-oxopropanoate(4). Of the present series, the 7-(2-thienyl) derivative (8a) exhibited good activity, especially against E. coli and Kl. pneumoniae (MIC = 2 μg / mL).
Keywords: Enaminones, aminoazoles, regioselective cyclization, 4-oxothieno[2,3-b]pyridines, antibacterial activity
Letters in Organic Chemistry
Title: Thienopyridone Antibacterials. Part IV[1]. Synthesis of Some N(7)- Heteroaryl-4-oxothieno[2,3-b]pyridine-5-carboxylic Acids and Esters
Volume: 7 Issue: 1
Author(s): Nuha I. Sweidan, Musa Z. Nazer, Mustafa M. El-Abadelah and Wolfgang Voelter
Affiliation:
Keywords: Enaminones, aminoazoles, regioselective cyclization, 4-oxothieno[2,3-b]pyridines, antibacterial activity
Abstract: A series of 7-heteroaryl-4-oxo-4,7-dihydrothieno[2,3-b]-pyridine-5-carboxylic acids (8a-d) and their methyl esters (7a-d) were prepared by cyclization of the respective 2-(2,5-dichlorothien-3-yl)-3-(N-heteroarylamino)acrylates (6a-d). The latter are accessible from methyl 2-(2,5-dichlorothien-3-yl)-3-ethoxyacrylate (5) which is obtained via methyl 3-(2,5-dichlorothien-3-yl)-3-oxopropanoate(4). Of the present series, the 7-(2-thienyl) derivative (8a) exhibited good activity, especially against E. coli and Kl. pneumoniae (MIC = 2 μg / mL).
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Cite this article as:
Sweidan I. Nuha, Nazer Z. Musa, El-Abadelah M. Mustafa and Voelter Wolfgang, Thienopyridone Antibacterials. Part IV[1]. Synthesis of Some N(7)- Heteroaryl-4-oxothieno[2,3-b]pyridine-5-carboxylic Acids and Esters, Letters in Organic Chemistry 2010; 7 (1) . https://dx.doi.org/10.2174/157017810790533977
DOI https://dx.doi.org/10.2174/157017810790533977 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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