Synthesis and systemic toxicity assessment of quinine-triazole scaffold with antiprotozoal potency

Nature products have been extensively used in the discovery and development of new drugs, as the most important source of drugs. The triazole ring is one of main pharmacophore of the nitrogen-containing heterocycles. Thus, a new class of triazole-containing natural product conjugates has been synthesised. These compounds reportedly exert anticancer, anti-inflammatory, antimicrobial, antiparasitic, antiviral, antioxidant, anti-Alzheimer, and enzyme inhibitory effects. This review summarises the research progress of triazole-containing natural product derivatives involved in medicinal chemistry in the past six years. This review provides insights and perspectives that will help scientists in the fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology.

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“…Quinine-triazole derivatives not only possess antimalarial activity 139 , but also they exhibit antileishmanial activity 149 . Sahu et al.…”

Section: Biological Activitiesmentioning

confidence: 99%

“…Sahu et al. 149 synthesised a series of quinine-triazole molecular hybrids. From the explored biological and toxicological evaluation it was observed that addition of triazole moiety to quinine resulted in reduction of toxicity of the conjugated scaffold.…”

Section: Biological Activitiesmentioning

confidence: 99%

Application of triazoles in the structural modification of natural products

Guo

Zheng-ai

Shen

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Incorporation of medicinally important pharmacophore aromatic ring/aliphatic moiety-substituted 1,2,3-triazole in quinine scaffolds has led to a novel series of derivatives. [42] All the synthesized quinine-triazoles have been investigated for antileishmanial properties in addition to other pharmacological activities. In comparison to quinine, all the triazole-incorporated molecules have exhibited higher activity revealing the benefit of 1,2,3-triazole.…”

Section: Antileishmanial Activitymentioning

confidence: 99%

“…Representation of quinoline scaffolds with decent antileishmanial property. [41][42][43][44] groups on phenyl rings has led to diminished antiprotozoal activity.…”

Section: Antileishmanial Activitymentioning

confidence: 99%

Quinoline: A Promising Scaffold in Recent Antiprotozoal Drug Discovery

Dorababu¹

2021

ChemistrySelect

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Protozoal infections malaria and leishmania have become most prevalent in recent times. A high death rate is reported world‐wide because of these diseases. Although there are only a few antiprotozoal drugs but could not be used anymore to cure protozoal diseases because of their toxic effects. Despite the non‐ceasing attempts to discover the drugs to cure malaria and leishmania, efficient drug‐design with low toxicity could not be achieved. A wide range of heterocyclic pharmacophores have been utilized to design efficient drugs. Amongst these heterocycles, quinoline bicycle is given a high priority, since a vast literature of quinoline derivatives relevant to potent pharmacological properties is available. The efficacy of the drugs lies upon the good bioavailability, favorable pharmacokinetics, and pharmacodynamics of the molecule. In view of these, the continual efforts are being put to bring about potent anti‐protozoal agents to clinical stage. In this review, the potential research done recently towards the anti‐protozoal drug‐design and discovery is compiled comprehensively. The importance of structural features attributed to remarkable activity is described taking consideration of structure‐activity relationship. Safety Index (SI), crucial for clinical efficiency of a drug is compared amongst a set of derivatives which involve inhibitory properties, in addition to the cytotoxic effects.

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“…Sahu et al published in 2019 [ 71 ] the synthesis of quinine-triazole systems with the aim to find new compounds via molecular hybridization [ 72 ] that can be addressed to two antiprotozoal targets that are malaria and leichmaniosis [ 72 , 73 ]. The synthetic route ( Scheme 11 ) started with activation through mesylation of the secondary alcohol of quinine generating the compound 39 and subsequent substitution with the azide group via a solution-based methodology [ 74 ].…”

Section: 123-triazole Systemsmentioning

confidence: 99%

Synthesis of Biologically Relevant 1,2,3- and 1,3,4-Triazoles: From Classical Pathway to Green Chemistry

2021

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Green Chemistry has become in the last two decades an increasing part of research interest. Nonconventional «green» sources for chemical reactions include micro-wave, mechanical mixing, visible light and ultrasound. 1,2,3-triazoles have important applications in pharmaceutical chemistry while their 1,2,4 counterparts are developed to a lesser extent. In the review presented here we will focus on synthesis of 1,2,3 and 1,2,4-triazole systems by means of classical and « green chemistry » conditions involving ultrasound chemistry and mechanochemistry. The focus will be on compounds/scaffolds that possess biological/pharmacophoric properties. Finally, we will also present the formal cycloreversion of 1,2,3-triazole compounds under mechanical forces and its potential use in biological systems.

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Synthesis and systemic toxicity assessment of quinine-triazole scaffold with antiprotozoal potency

Cited by 37 publications

References 26 publications

Application of triazoles in the structural modification of natural products

Application of triazoles in the structural modification of natural products

Quinoline: A Promising Scaffold in Recent Antiprotozoal Drug Discovery

Synthesis of Biologically Relevant 1,2,3- and 1,3,4-Triazoles: From Classical Pathway to Green Chemistry

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