Design, synthesis, biological evaluation and molecular modelling studies of novel quinoline derivatives against Mycobacterium tuberculosis

Upadhayaya, Ram Shankar; Vandavasi, Jaya Kishore; Vasireddy, Nageswara Rao; Sharma, Vivek; Dixit, Shailesh S.; Chattopadhyaya, J.

doi:10.1016/j.bmc.2009.02.026

Cited by 106 publications

(57 citation statements)

References 28 publications

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“…Substituted-3-benzyl-6-bromo-2-methoxy-quinoline analogs, that is, 8a, 8b, 8c and 8d, exhibited 94.2%, 99.5%, 92.5% and 100% growth inhibition of M. tuberculosis H 37 Rv, respectively, at a concentration of 6.25 mg/mL. However, their amide derivatives (9) showed poor activity (less than 22% growth inhibition) 14 . In the cytotoxicity study on murine macrophage cells, 8c showed 100% cell viability at the concentration of 10 mg/mL.…”

Section: 3-disubstituted Quinolinesmentioning

confidence: 99%

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Singh

Kaur

Mangla

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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Tuberculosis (TB) is still a major health concern worldwide. The increasing incidences of multi-drug-resistant tuberculosis (MDR-TB) necessitate the development of new anti-TB drugs acting via novel mode of action. The search of newer drugs for TB led to the identification of several quinoline-based antimycobacterial agents against both the drug-sensitive and MDR-TB. These agents have been designed by substituting quinoline scaffold with diverse chemical functionalities as well as by modifying quinoline/quinolone-based antibacterial drugs. Several of quinoline/quinolone derivatives displayed excellent antimycobacterial activity and were found free of cytotoxicity. This review highlights the critical aspects of design and structure-activity relationship of quinoline-and quinolone-based antimycobacterial agents.

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Section: 3-disubstituted Quinolinesmentioning

confidence: 99%

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Singh

Kaur

Mangla

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…To achieve this we planned to build a homology model of pathogenic MTB rotor along with the subunit-a, so as to generate the interface which is known to host the binding site of bedaquiline. Previous workers performed molecular docking studies employing homology model of ac12 protein complex using E. coli F1F0 ATP synthase subunit-a and rotor complex (PDB ID: 1C17) as template that share relatively low sequence similarity (Table-1) [16][17][18][19]. One advantage with 1C17 template, despite low sequence identity with query sequence is presence of both subunit-a and entire rotor with c12 configuration.…”

Section: Methodsmentioning

confidence: 99%

in silico Quest Guided by Physico-Chemical Descriptors of Bedaquiline for New Scaffolds with Potential Inhibitory Capacity against Homology Model of Mycobacterium F1F0 ATP Synthase

Munnaluri¹,

Manga²

2018

Asian J. Chem.

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As the first US FDA approved drug for treating pulmonary multi drug resistant tuberculosis (MDR-TB) in the last 40 years, bedaquiline (TMC207, Sirturo TM ) stands out as cynosure in the circles of synthetic chemists exploring new therapeutics against tuberculosis. The remarkable efficacy of bedaquiline in treating tuberuculosis lies in its ability to target the energy metabolism that affects both replicating as well as dormant forms of M. tuberculosis (MTB). Despite its promising antitubercular profile, bedaquiline raises serious concern with its string of side effects and emergence of resistant strains, warrants a quest for better substitutes. In the present work, we employed in silico methods like homology modeling and virtual screening to zero in on molecules that exhibit high affinity at the binding site of bedaquiline.

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“…These compounds were found to be nontoxic against J774 cell line up to the concentration 100 μg/ml [125]. In search of novel potent quinoline derivatives, quinoline derivatives consisting of triazolo, ureido and thioureido substituents at C-6 position, of these, ureido derivative (32a) and triazolo derivative (32b) have shown moderate activity of MIC 3.125 μg/mL against M. tuberculosis H37Rv [126]. With the same motivation, a series of amino acid conjugates of 4-(adamantan-1-yl) group containing quinolines.…”

Section: Quinoline and Quinoxaline Derivativesmentioning

confidence: 99%

Role of quinolones and quinoxaline derivatives in the advancement of treatment of tuberculosis

Asif

2015

IJSW

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The need of new chemotherapeutic drugs to improve tuberculosis control and treatment particularly against multidrugresistant (MDR) and extensively drug resistant (XDR) strains of Mycobacterium. The atitubercular drugs are used in current chemotherapy have different chemical moieties. In this review, we provide an overview of the quinolone drugs as an antitubercular drug. Generally quinolone drugs are mainly used against many gram-positive and gram-negative bacterial infections including resistance strains also. Various quinolones are being used to control and treatment of tubercular infections including MDR, XDR and atypical Mycobacterium strains. Fluoroquinolones are an important quinolones, especially for strains that are resistant to first-line agents.

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Design, synthesis, biological evaluation and molecular modelling studies of novel quinoline derivatives against Mycobacterium tuberculosis

Cited by 106 publications

References 28 publications

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

in silico Quest Guided by Physico-Chemical Descriptors of Bedaquiline for New Scaffolds with Potential Inhibitory Capacity against Homology Model of Mycobacterium F1F0 ATP Synthase

Role of quinolones and quinoxaline derivatives in the advancement of treatment of tuberculosis

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