Design and synthesis of 4-Aminoquinoline-isoindoline-dione-isoniazid triads as potential anti-mycobacterials

Rani, Anu; Johansen, Matt D.; Roquet-Banères, Françoise; Kremer, Laurent; Awolade, Paul; Ebenezer, Oluwakemi; Singh, Parvesh; Sumanjit,; Kumar, Vipan

doi:10.1016/j.bmcl.2020.127576

Cited by 17 publications

(4 citation statements)

References 47 publications

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“…Further, SAR studies indicated that the anti‐TB activity of triads depends upon two factors: first, upon the carbon chain length between quinoline and isoindoline, and second, upon the position of pharmacophores (isoniazid and 4‐aminoquinoline) around isoindoline nucleus. [ 72 ]…”

Section: Anti‐infective Potential Of 4‐substituted Quinolinesmentioning

confidence: 99%

“…Further, SAR studies indicated that the anti-TB activity of triads depends upon two factors: first, upon the carbon chain length between quinoline and isoindoline, and second, upon the position of pharmacophores (isoniazid and 4-aminoquinoline) around isoindoline nucleus. [72] da Silva sensitive strain (ATCC 27294) and resistant strain (SR 2571/0215 and T113/09) of M. tuberculosis using MABA method. Among screened derivatives, compound 57 (Figure 19) was the most potent anti-TB agent with MIC values of 12 and 5 µM against both sensitive strain and resistant strain, respectively.…”

Section: -Substituted Quinoline As Antitubercular Agentsmentioning

confidence: 99%

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Spotlight on 4‐substituted quinolines as potential anti‐infective agents: Journey beyond chloroquine

Goyal

Kharkwal

Piplani

et al. 2022

Archiv der Pharmazie

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Continued emerging resistance of pathogens against the clinically approved candidates and their associated limitations continuously demand newer agents having better potency with a more suited safety profile. Quinoline nuclei containing scaffolds of natural and synthetic origin have been documented for diverse types of pharmacological activities, and a number of drugs are clinically approved. In the present review, we unprecedentedly covered the biological potential of 4-substituted quinoline and elaborated a rationale for its special privilege to afford the significant number of approved clinical drugs, particularly against infectious pathogens. Compounds with 4-substituted quinoline are well documented for antimalarial activity, but in the last two decades, they have been extensively explored for activity against cancer, tuberculosis, and several other pathogens including viruses, bacteria, fungi, and other infectious pathogens. In the present study, the anti-infective spectrum of this scaffold is discussed against viruses, mycobacteria, malarial parasites, and fungal and bacterial strains, along with recent updates in this area, with special emphasis on the structure-activity relationship.

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Section: Anti‐infective Potential Of 4‐substituted Quinolinesmentioning

confidence: 99%

Section: -Substituted Quinoline As Antitubercular Agentsmentioning

confidence: 99%

Spotlight on 4‐substituted quinolines as potential anti‐infective agents: Journey beyond chloroquine

Goyal

Kharkwal

Piplani

et al. 2022

Archiv der Pharmazie

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“…The coupling/fusion of two or more bioactive heterocyclic pharmacophores into a single multifaceted skeleton capable of modulating multiple targets at the same time is known as “molecular hybridization” (Meunier, 2008; Mishra & Singh, 2016). This hybridization approach is a very innovative and powerful synthetic concept which has revolutionized the field of medicinal chemistry with the synthesis of bioactive molecules with novel biological activities (Lal, Kumar, et al, 2018; Rani et al, 2020). These hybrid molecules not only diversify the biological spectrum but also help in overcoming the drug cross‐resistance, reducing the drug toxicity thereby enhancing the efficacy of the parent drug (Gao, Zhang, et al, 2019; Xu et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

A minireview of 1,2,3‐triazole hybrids with O‐heterocycles as leads in medicinal chemistry

Saroha

Kumar

et al. 2021

Chem Biol Drug Des

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Over the past few decades, the dynamic progress in the synthesis and screening of heterocyclic compounds against various targets has made a significant contribution in the field of medicinal chemistry. Among the wide array of heterocyclic compounds, triazole moiety has attracted the attention of researchers owing to its vast therapeutic potential and easy preparation via copper and ruthenium-catalyzed azide-alkyne cycloaddition reactions. Triazole skeletons are found as major structural components in a different class of drugs possessing diverse pharmacological profiles including anti-cancer, anti-bacterial, anti-fungal, anti-viral, anti-oxidant, anti-inflammatory, anti-diabetic, anti-tubercular, and anti-depressant among B. subtilis(MIC) 26a 1.56 µg/mL 26b 3.125 µg/mL 26c 3.125 µg/mL S. aureus(MIC) 26a 1.56 µg/mL 26b 3.125 µg/mL 26c 1.56 µg/mL A. nigar(MIC) 26d 3.125 µg/mL 26e 3.125 µg/mL C. albians(MIC) 26d 3.125 µg/mL 26e 3.125 µg/mL gram negative bacteria(MIC) 26a 3.125 µg/mL 26b 3.125 µg/mL 26c 3.125 µg/mL

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“…It was observed that in recent years, isoniazid and its derivatives have received attention and are being widely studied. The derivatives of isoniazid are evaluated for their various biological activities, such as anti-inflammatory [8], anticancer [9,10], antimicrobial [11][12][13], anti-tubercular [2,11,[14][15][16][17], and in the treatment of Alzheimer's disease [18].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis of Schiff Bases of Isoniazid and Evaluation of Their Anti-Proliferative and Antibacterial Activities

Al-Hiyari

Shakya

Naik

et al. 2021

Molbank

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Three new Schiff bases of isoniazid were synthesized using microwave-assisted synthesis and conventional condensation with aromatic aldehydes. Synthesized compounds were characterized using elemental analysis, IR, NMR, and Mass spectroscopy. Synthesized compounds were evaluated for antiproliferative activity against MCF-7 cell line. The IC50 values were from 125 to 276 µM. The compounds were also evaluated for antibacterial activity against Staphylococcus aureus and Escherichia coli. Results showed that the synthesized compounds produce significant antibacterial activity in vitro. Inhibition of compounds ranged from 13 to 18 mm.

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Design and synthesis of 4-Aminoquinoline-isoindoline-dione-isoniazid triads as potential anti-mycobacterials

Cited by 17 publications

References 47 publications

Spotlight on 4‐substituted quinolines as potential anti‐infective agents: Journey beyond chloroquine

Spotlight on 4‐substituted quinolines as potential anti‐infective agents: Journey beyond chloroquine

A minireview of 1,2,3‐triazole hybrids with O‐heterocycles as leads in medicinal chemistry

Microwave-Assisted Synthesis of Schiff Bases of Isoniazid and Evaluation of Their Anti-Proliferative and Antibacterial Activities

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