Synthesis and Antimalarial Activity Study of Some New Mannich Bases of 7-Chloro-4-Aminoquinoline

Roy, Susanta Sinha; Chetia, Dipak; Rudrapal, Mithun; Prakash, Anil

doi:10.2174/1573406411309030008

Cited by 15 publications

(14 citation statements)

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“…Antimalarial activity of analogues 206 of isoquine ( Fig. 38) has also been evaluated, but regardless of the nature of the amine in the aminomethyl moiety, their activity was considerably lower than that of reference drug chloroquine [315,316]. Use of primary amines derived from bicyclic scaffolds for the synthesis of novel isoquine analogues led to the discovery of 207 (Fig.…”

Section: Antimalarial Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

271

110

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The biological activity of Mannich bases, a structurally heterogeneous class of chemical compounds that are generated from various substrates through the introduction of an aminomethyl function by means of the Mannich reaction, is surveyed, with emphasis on the relationship between structure and biological activity. The review covers extensively the literature reports that have disclosed Mannich bases as anticancer and cytotoxic agents, or compounds with potential antibacterial and antifungal activity in the last decade. The most relevant studies on the activity of Mannich bases as antimycobacterial agents, antimalarials, or antiviral candidates have been included as well. The review contains also a thorough coverage of anticonvulsant, anti-inflammatory, analgesic and antioxidant activities of Mannich bases. In addition, several minor biological activities of Mannich bases, such as their ability to regulate blood pressure or inhibit platelet aggregation, their antiparasitic and anti-ulcer effects, as well as their use as agents for the treatment of mental disorders have been presented. The review gives in the end a brief overview of the potential of Mannich bases as inhibitors of various enzymes or ligands for several receptors.

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Section: Antimalarial Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

271

110

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“…Five well-known species ( Plasmodium falciparum , Plasmodium vivax , Plasmodium malariae , Plasmodium ovale and Plasmodium knowlesi ) have been reported so far to be the causative organisms of malaria in human. Among these five organisms, P. falciparum is the most widespread and pernicious species which causes potentially fatal malaria such as cerebral malaria and most of the malaria-related deaths worldwide 2–4. In patients with severe and complicated malaria caused by P. falciparum , the mortality rate accounts for 20%–50% when left untreated 1…”

Section: Introductionmentioning

confidence: 99%

Endoperoxide antimalarials: development, structural diversity and pharmacodynamic aspects with reference to 1,2,4-trioxane-based structural scaffold

Rudrapal¹,

Chetia²

2016

DDDT

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Malaria disease continues to be a major health problem worldwide due to the emergence of multidrug-resistant strains of Plasmodium falciparum. In recent days, artemisinin (ART)-based drugs and combination therapies remain the drugs of choice for resistant P. falciparum malaria. However, resistance to ART-based drugs has begun to appear in some parts of the world. Endoperoxide compounds (natural/semisynthetic/synthetic) representing a huge number of antimalarial agents possess a wide structural diversity with a desired antimalarial effectiveness against resistant P. falciparum malaria. The 1,2,4-trioxane ring system lacking the lactone ring that constitutes the most important endoperoxide structural scaffold is believed to be the key pharmacophoric moiety and is primarily responsible for the pharmacodynamic potential of endoperoxide-based antimalarials. Due to this reason, research into endoperoxide, particularly 1,2,4-trioxane-, 1,2,4-trioxolane- and 1,2,4,5-teraoxane-based scaffolds, has gained significant interest in recent years for developing antimalarial drugs against resistant malaria. In this paper, a comprehensive effort has been made to review the development of endoperoxide antimalarials from traditional antimalarial leads (natural/semisynthetic) and structural diversity of endoperoxide molecules derived from 1,2,4-trioxane-, 1,2,4-trioxolane- and 1,2,4,5-teraoxane-based structural scaffolds, including their chimeric (hybrid) molecules, which are newer and potent antimalarial agents.

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“…21,22,23 Two strains were used for the study, one is CQ-sensitive 3D-7 and the other is CQ-resistant RKL-2. All the test compounds, 4a-j were initially screened at two fixed doses, 5 µg/ml and 50 µg/ml against CQ-sensitive strain.…”

Section: Antimalarial Activity Evaluationmentioning

confidence: 99%

Synthesis and Antimalarial Activity of Lawsone Mannich Base Derivatives

Arundhati¹,

Chetia²,

Rudrapal³

2018

IJPER

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Introduction:The emergence of multi-drug resistant strains of Plasmodium falciparum has increasingly become a serious health problem worldwide. To address this challenging issue, there is an urgent need to discover and develop novel and potent antimalarial agents. Materials and Methods: A new series of lawsone Mannich base derivatives were synthesized, characterized (IR, NMR and Mass) and evaluated for in vitro for antimalarial activity against chloroquine (CQ)-sensitive and CQ-resistant strains of P. falciparum. Results and Discussion: Among synthesized compounds, five compounds showed good antimalarial activity against both chloroquine (CQ)-sensitive (3D-7) and -resistant (RKL-2) strains of P. falciparum, which, however, was considerably less than that of the standard reference drug, CQ. The antimalarial activity of these five compounds was found better against sensitive (IC 50 = 0.411-0.502 μg/ml) strain than the resistant (IC 50 = 1.391-2.394 μg/ml) one. The IC50 values for CQ were 0.044 μg/ml and 0.216 μg/ml against sensitive and resistant strains of P. falciparum, respectively. SAR study suggests that antimalarial potential of lawsone structural scaffold can be modulated by different substitution pattern like Mannich base substitution (alkyl/aryl/heteroaryl substituted aminoalkyl moiety) at the C-3 position of 1,4-naphthoquinone ring system. Conclusion: Owing to their antimalarial effectiveness, lawsone derived aminonaphthoquinones can be used as lead structure(s) in the development of yet more potent antimalarial agents.

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Synthesis and Antimalarial Activity Study of Some New Mannich Bases of 7-Chloro-4-Aminoquinoline

Cited by 15 publications

References 0 publications

Mannich bases in medicinal chemistry and drug design

Mannich bases in medicinal chemistry and drug design

Endoperoxide antimalarials: development, structural diversity and pharmacodynamic aspects with reference to 1,2,4-trioxane-based structural scaffold

Synthesis and Antimalarial Activity of Lawsone Mannich Base Derivatives

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