A microwave-assisted, facile, regioselective Friedländer synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2- b ]quinolines

Balamurugan, Kamaraj; Jeyachandran, Veerappan; Perumal, S.; Manjashetty, Thimmappa H.; Yogeeswari, Perumal; Sriram, Dharmarajan

doi:10.1016/j.ejmech.2009.11.011

Cited by 50 publications

(19 citation statements)

References 52 publications

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“…Heterocyclic systems containing a quinoline nucleus are an important group of compounds in medicinal chemistry, and are ubiquitous sub-structures associated with biologically active natural products [1–4]. Some quinoline compounds especially those containing heterocyclic systems at 2-position have been shown to display a wide spectrum of biological activities such as cytotoxic, anti-inflammatory and antifungal behavior [5–6].…”

Section: Introductionmentioning

confidence: 99%

First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives

Gao¹,

Liu²,

Jiang³

et al. 2011

Beilstein J. Org. Chem.

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SummaryA facile and inexpensive synthesis of a series of novel methylenedioxy-bearing 2-(benzofuran-2-yl)-quinoline-3-carboxylic acid derivatives 3a–h via the one-pot reaction of ethyl 2-chloromethyl-6,7-methylenedioxyquinoline-3-carboxylate (5) with various substituted salicylaldehydes 6a–g as well as 2-hydroxy-1-naphthaldehyde (6h) is described. Substrate 5 was synthesized by the Friedländer condensation reaction of 2-amino-4,5-methylenedioxybenzaldehyde (4) with ethyl 4-chloro-3-oxobutanoate using KHSO4 as catalyst under ultrasound irradiation conditions. The targeted compounds 3a–h were obtained in good yields of 52–82% and their structures were established based on spectral data and elemental analyses.

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Section: Introductionmentioning

confidence: 99%

First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives

Gao¹,

Liu²,

Jiang³

et al. 2011

Beilstein J. Org. Chem.

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“…In this assay, 28a showed 100% cell viability at the dose of 100 mg/mL and thus found to be noncytotoxic to the host cells in the effective concentrations (MIC 2.5 mg/mL) to inhibit the growth M. tuberculosis 23 . De Souza et al studied the effect of number of carbon in intermediate chain between two nitrogen atoms (as shown in 29) of 4-amino-quinolines on the antimycobacterial activity (29). The compounds with two to four carbon length showed poor activity (MIC: 100 mg/mL).…”

Section: -Substituted Quinolinesmentioning

confidence: 99%

“…Also, at C-7 position (R 2 ), the presence of chlorine atom considerably improved the activity. It may be suggested that electronwithdrawing substituents at R 1 and R 2 positions are conducive for the activity 29 . .…”

Section: -Substituted 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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“…The SAR of thienoquinolines 1 revealed that hybrids with –Cl at the C‐7 position displayed significantly greater activity than the corresponding unsubstituted derivatives against both MTB and MDR‐TB; electron‐withdrawing groups such as halogen or –NO 2 in the phenyl ring of the thiophene ring showed better activity than these with electron‐donating groups like alkyl; disubstitution in the phenyl ring enhances the activity when compared with monosubstitution . The hybrid 1a [minimum inhibitory concentration (MIC): 0.95 μM] was far more potent than the references INH, RIF, EMB, and ciprofloxacin (MIC: 11.38, 3.80, 61.18, and 37.73 μM) against MDR‐TB.…”

Section: Quinoline‐based Derivativesmentioning

confidence: 99%

Quinoline Derivatives with Potential Activity Against Multidrug‐resistant Tuberculosis

Zhou

et al. 2018

Journal of Heterocyclic Chem

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Tuberculosis (TB), which affects primarily the lungs (pulmonary TB) apart from other vital organs, is a life‐threatening chronic deadliest infectious disease caused by members of Mycobacterium tuberculosis (MTB) complex and mainly by MTB itself. The emergence of MTB new virulent forms that are resistant to some or all first‐line and second‐line anti‐TB agents, including multidrug‐resistant (MDR), extensively drug‐resistant, and totally drug‐resistant strains has further aggravated the spread of this disease and was increased up to an alarming level in the recent decades. More than ever, it is imperative to develop novel, high effective, and fast acting anti‐TB drugs to prevent the spread of TB, particularly in its hard‐to‐kill MDR‐TB, extensively drug‐resistant‐TB, and totally drug‐resistant‐TB strains. In recent years, numerous compounds have been synthesized for this purpose, but only a handful of compounds have entered human trials after the discovery of rifampicin, reflecting the inherent difficulties of developing new anti‐TB agents. Despite of bedaquiline and delamanid have received approval from many countries for treatment of MDR‐TB infected patients, both drugs are associated with serious side effects and are only recommended for those MDR‐TB patients without other treatment options. All these aforementioned facts make it an urgent need to develop novel drugs. Quinoline‐based derivatives including quinolones ex biological activities, and some of them displayed excellent in vitro and in vivo activities against MDR‐TB. This review outlines the recent developments of quinoline‐based derivatives with potential activity against MDR‐TB as well as the structure–activity relationship.

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A microwave-assisted, facile, regioselective Friedländer synthesis and antitubercular evaluation of 2,9-diaryl-2,3-dihydrothieno-[3,2- b ]quinolines

Cited by 50 publications

References 52 publications

First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives

First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Quinoline Derivatives with Potential Activity Against Multidrug‐resistant Tuberculosis

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