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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences


IMPACT FACTOR 2018: 0.961

CiteScore 2018: 0.91

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Source Normalized Impact per Paper (SNIP) 2018: 0.505

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1865-7117
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Volume 71, Issue 1

Issues

Heterocycles [h]-fused to 4-oxoquinoline-3-carboxylic acid. Part XI: Synthesis and antibacterial activity of 4-fluoro-6-oxoimidazo[4,5-h]quinoline-7-carboxylic acids

Jalal A. Zahra / Raed A. Al-Qawasmeh / Mustafa M. El-Abadelah / Mohammed M. Abadleh / Franca Zani
  • Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27/A, Parma 43124, Italy
  • Other articles by this author:
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/ Matteo Incerti
  • Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27/A, Parma 43124, Italy
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/ Paola Vicini
  • Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27/A, Parma 43124, Italy
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/ Wolfgang Voelter
  • Corresponding author
  • Interfakultäres Institut für Biochemie, Universität Tübingen, Hoppe-Seyler-Straße 4, 72076 Tübingen, Germany
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Published Online: 2015-12-11 | DOI: https://doi.org/10.1515/znb-2015-0126

Abstract

A series of 2-hetaryl-4-fluoro-9-cyclopropyl-6-oxo-1H-imidazo[4,5-h]quinoline-7-carboxylic esters (3a–f) and their corresponding acids 4af have been prepared via microwave-assisted cyclocondensation reaction with some hetarene carboxaldehydes. The structures for these new esters and acids are based on spectral (IR, MS, and NMR) data. The in vitro antimicrobial assay of 4af hetaryl derivatives, their aryl analogues 1dg, and the imidazo-unsubstituted acid 1a showed that all of these tricyclic heterocycles possess a good level of antibacterial activity. Among them, compound 1a exhibited the highest effect against both, Gram-positive (minimum inhibitory concentrations [MICs] 0.15–3.0 μg mL–1) and Gram-negative bacteria (MICs 0.7–3.0 μg mL–1). An excellent activity was recorded also for the halo-phenyl derivatives 1f,g and for the furan derivatives 4e,f, especially toward Gram-positive strains and Bacillus subtilis and Haemophilus influenzae, respectively.

Keywords: antibacterial activity; cyclocondensation; 7,8-diaminofluoroquinolone; hetarene carboxaldehydes; microwave irradiation

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About the article

Corresponding authors: Jalal A. Zahra, Faculty of Science, Chemistry Department, The University of Jordan, Amman 11942, Jordan, e-mail: ; and Wolfgang Voelter, Interfakultäres Institut für Biochemie, Universität Tübingen, Hoppe-Seyler-Straße 4, 72076 Tübingen, Germany, e-mail:


Received: 2015-07-26

Accepted: 2015-10-20

Published Online: 2015-12-11

Published in Print: 2016-01-01


Citation Information: Zeitschrift für Naturforschung B, Volume 71, Issue 1, Pages 37–44, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2015-0126.

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