Design, synthesis, and biological evaluation of new quinoline-based heterocyclic derivatives as novel antibacterial agen

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ORIGINAL PAPER

Design, synthesis, and biological evaluation of new quinoline‑based heterocyclic derivatives as novel antibacterial agents Ghazwan Ali Salman1 · Dhafer S. Zinad2 · Ahmed Mahal3,4  Received: 13 July 2020 / Accepted: 7 September 2020 © Springer-Verlag GmbH Austria, part of Springer Nature 2020

Abstract A novel series of quinolone-based heterocyclic derivatives including thiadiazine, thiadiazoles, and triazole were synthesized and their in vitro antibacterial activity against Gram-positive and Gram-negative bacteria were evaluated. Newly synthesized derivatives have been obtained in good yields ranging from 65 to 80%. The synthesized derivatives have been characterized and their structures identified using spectroscopic analysis including NMR, FT-IR, and mass techniques. Most of compounds exhibited moderate-to-good antibacterial activity against all four bacterial strains and are significantly more active than ampicillin. Compounds showed relatively good anti-bacterial activity compared to moderate activity of other compounds. The results obtained herein are important for further structure modifications of quinoline bearing heterocyclic moiety and the exploitation of the therapeutic potential of quinoline derivatives as antibacterial agents. Graphic abstract

Keywords  Antibacterial · Drug discovery · Heterocycles · Quinoline · Synthesis

Introduction

* Ghazwan Ali Salman [email protected] * Ahmed Mahal [email protected] 1



Department of Chemistry, College of Sciences, Mustansiriyah University, 10052 Baghdad, Iraq

2



Applied Science Department, University of Technology, Baghdad 10001, Iraq

3

Key Laboratory of Plant Resources Conservation and Sustainable Utilization and Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People’s Republic of China

4

Guangzhou HC Pharmaceutical Co., Ltd, Guangzhou 510663, People’s Republic of China





Heterocycles are promising agents in the development of drug discovery and medicinal chemistry as well and heterocycles containing compounds have broad diversity of applications in pharmaceutical industry [1–9]. Quinolines are found in many natural products and exhibit remarkable activities as antimalarial [10], antibiotic [11], anti-tuberculosis [12], anticancer [13], and anti-HIV [14] agents. Various triazole and thiadiazole derivatives are among of the promising bioactive groups of heterocyclic molecules and show a broad range of pharmacological activities such as antimicrobial agents [15–18]. These heterocycles possess additional biological activities including anti-inflammatory [19], anticancer [20], and antifungal activities [21]. In addition to that, thiadiazines play an important role in medicinal chemistry and drug discovery and they have been reported to possess antibacterial activity [22]. Modification of quinolone

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scaffold by inserting other heterocycle moieties such as triazole and thiadiazole leading to enhance the bioactivity o