A trio of quinoline-isoniazid-phthalimide with promising antiplasmodial potential: Synthesis, in-vitro evaluation and heme-polymerization inhibition studies

Rani, Anu; Sharma, Anny; Legac, Jenny; Rosenthal, Philip J.; Singh, Parvesh; Kumar, Vipan

doi:10.1016/j.bmc.2021.116159

Cited by 21 publications

(8 citation statements)

References 34 publications

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“…The antiplasmodial activity of the 4aminoquinoline-phthalimides derivatives differs as the spacer length changes, as seen by IC 50 values of 50.8, 30.2, and 43.2 nM for 60, 61, and 62 respectively. The triads were made by substituting the quinolone with isoniazid (INH) around the phthalimide core giving rise to the most promising derivative in series 63 with an IC 50 value of 11 nM (Rani et al, 2021).…”

Section: Structural Activity Relationship (Sar) Of Some Quinoline Hyb...mentioning

confidence: 99%

Recent advances in functionalized quinoline scaffolds and hybrids—Exceptional pharmacophore in therapeutic medicine

Elebiju

Ajani²,

Oduselu³

et al. 2023

Front. Chem.

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Quinoline is one of the most common nitrogen-containing heterocycles owing to its fascinating pharmacological properties and synthetic value in organic and pharmaceutical chemistry. Functionalization of this moiety at different positions has allowed for varying pharmacological activities of its derivative. Several publications over the last few decades have specified various methods of synthesis. This includes classical methods of synthesizing the primary quinoline derivatives and efficient methods that reduce reaction time with increased yield employing procedures that fulfill one of the twelve green chemistry principles, “safer solvent”. The metal nanoparticle-catalyzed reaction also serves as a potent and effective technique for the synthesis of quinoline with excellent atom efficiency. The primary focus of this review is to highlight the routes to synthesizing functionalized quinoline derivatives, including hybrids that have moieties with predetermined activities bound to the quinoline moiety which are of interest in synthesizing drug candidates with dual modes of action, overcoming toxicity, and resistance amongst others. This was achieved using updated literature, stating the biological activities and mechanisms through which these compounds administer relief. The ADMET studies and Structure-Activity Relationship (SAR) of novel derivatives were also highlighted to explore the drug-likeness of the quinoline-hybrids and the influence of substituent characteristics and position on the biological activity of the compounds.

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Section: Structural Activity Relationship (Sar) Of Some Quinoline Hyb...mentioning

confidence: 99%

Recent advances in functionalized quinoline scaffolds and hybrids—Exceptional pharmacophore in therapeutic medicine

Elebiju

Ajani²,

Oduselu³

et al. 2023

Front. Chem.

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“…It undergoes amide coupling with isoniazid to form a quinoline-isoniazidphthalimide derivative (11C). It acts as the suitable starting point for developing a new antimalarial agent was reported by Anu Rani et al [14]…”

Section: Quinoline-isoniazid-phthalimide Derivativementioning

confidence: 99%

A Mini-Review On The Current Scenario Of Quinoline Scaffolds For Antimalarial Activity

Ilakiyalakshmi¹,

Arumugam²

2022

ECS Trans.

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Antimalarial agents are an important key for the prevention and eradication of malaria. The heterocyclic aromatic quinoline scaffold is a favored structure in drug development because its derivatives have a wide range of biological properties. The quinoline family contains a lot of antimalarial agents like chloroquine, piperaquine, quinine, etc. Chloroquine had been a significant antimalarial agent for more than five decades. To enhance the efficacy in malarial treatment a new system of several other quinoline-based drugs has been synthesized. This mini-review intends to provide a literature overview of antimalarial compounds containing a quinoline core, encompassing papers from 2018 to the present along with the synthesis and pertinent figures. It could be useful for researchers to design more effective antimalarial drugs in the future.

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“…16 These modifications are based on amide linkages that utilize Pht as a parent scaffold and amino acids as a complimentary scaffold, as they possess the potential to serve as drug synthons. 26 Further, heterocyclic moieties i.e., piperazines and cyclic amines, are significant constituents in synthesizing substituted amide linkages. 27,28,29 Consistent with previously published data, certain analogs featuring C2 symmetry with piperazine have exhibited better outcomes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel phthalimide-based piperazine conjugated analogs as anti-malarial agents

Bansal,

Kumar,

Rathi

2023

CBL

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In the present report, we synthesized twelve novel phthalimide analogs and evaluated for antiplasmodial efficacy on Plasmodium falciparum culture. Two molecules exhibited significant inhibition percentages at 1 µM concentration without any apparent cytotoxicity on HepG2 cells. Inhibitory concentration (IC50) for both the hit compounds 6d and 8a was observed in micromolar range, 1.20 µM and 1.66 µM, respectively. Extensive in silico studies conducted indicate plasmepsin IX as a possible target for inhibitory activity of the reported molecules.

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A trio of quinoline-isoniazid-phthalimide with promising antiplasmodial potential: Synthesis, in-vitro evaluation and heme-polymerization inhibition studies

Cited by 21 publications

References 34 publications

Recent advances in functionalized quinoline scaffolds and hybrids—Exceptional pharmacophore in therapeutic medicine

Recent advances in functionalized quinoline scaffolds and hybrids—Exceptional pharmacophore in therapeutic medicine

A Mini-Review On The Current Scenario Of Quinoline Scaffolds For Antimalarial Activity

Synthesis of novel phthalimide-based piperazine conjugated analogs as anti-malarial agents

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