Synthesis and biological evaluation of chalcones as potential antileishmanial agents

Gupta, Shweta; Shivahare, Rahul; Korthikunta, Venkateswarlu; Singh, Rohit; Gupta, Suman; Narender, Tadigoppula

doi:10.1016/j.ejmech.2014.05.034

Cited by 38 publications

(21 citation statements)

References 34 publications

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“…major and L . donovani is related to mitochondrial alterations [ 56 ]. Synthetic analogues of chalcone isolates of Crotalaria ramosissima show enhanced in vitro and in vivo activity as compared to the natural chalcone [ 57 ].…”

Section: Discussionmentioning

confidence: 99%

Cinnamic Acid Bornyl Ester Derivatives from Valeriana wallichii Exhibit Antileishmanial In Vivo Activity in Leishmania major-Infected BALB/c Mice

Masic¹,

Hernandez²,

Hazra

et al. 2015

PLoS ONE

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Human leishmaniasis covers a broad spectrum of clinical manifestations ranging from self-healing cutaneous leishmaniasis to severe and lethal visceral leishmaniasis caused among other species by Leishmania major or Leishmania donovani, respectively. Some drug candidates are in clinical trials to substitute current therapies, which are facing emerging drug-resistance accompanied with serious side effects. Here, two cinnamic acid bornyl ester derivatives (1 and 2) were assessed for their antileishmanial activity. Good selectivity and antileishmanial activity of bornyl 3-phenylpropanoate (2) in vitro prompted the antileishmanial assessment in vivo. For this purpose, BALB/c mice were infected with Leishmania major promastigotes and treated with three doses of 50 mg/kg/day of compound 2. The treatment prevented the characteristic swelling at the site of infection and correlated with reduced parasite burden. Transmitted light microscopy and transmission electron microscopy of Leishmania major promastigotes revealed that compounds 1 and 2 induce mitochondrial swelling. Subsequent studies on Leishmania major promastigotes showed the loss of mitochondrial transmembrane potential (ΔΨm) as a putative mode of action. As the cinnamic acid bornyl ester derivatives 1 and 2 had exhibited antileishmanial activity in vitro, and compound 2 in Leishmania major-infected BALB/c mice in vivo, they can be regarded as possible lead structures for the development of new antileishmanial therapeutic approaches.

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Section: Discussionmentioning

confidence: 99%

Cinnamic Acid Bornyl Ester Derivatives from Valeriana wallichii Exhibit Antileishmanial In Vivo Activity in Leishmania major-Infected BALB/c Mice

Masic¹,

Hernandez²,

Hazra

et al. 2015

PLoS ONE

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show abstract

“…20) In addition, microwave irradiation enhanced the reaction rate with a slightly improved chemical yield than the reflux conditions described in a previous study. 19) However, interestingly, chromene annulations of hydroxycoumaranone 5 to synthesize chromene 8 under microwave irradiation and reflux conditions afforded only a mixture of aldol adducts. This may be attributed to the difference in nucleophilicity of the carbonyl α-carbon between the 3-coumaranone and acetophenone structures.…”

Section: Resultsmentioning

confidence: 99%

“…Pyridine-catalyzed condensation 18) under microwave irradiation between 2,4-dihydroxyacetophenone 4 and 3-methyl-2-butenal regioselectively gave the known chromene 6, 19) which was subjected to hydrogenation using palladium on carbon as a catalyst to afford chromane 3. This two-step procedure to obtain the chromane structure was more regioselective than previously described one-step reaction using isoprene.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of the Proposed Structure of Damaurone D and Evaluation of Its Anti-inflammatory Activity

Han

Wang

Bae

2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Chalcones are multifunctional molecules that possess promising pharmacological activities. Chalcones have been found useful as anticancer [23][24][25], antioxidant [26][27][28][29], antiinflammatory [30][31][32], anti-microbial [23,[33][34][35][36], anti-tubercular [34,37,38], antileishmanial [39], antimalarial [40][41][42], anthelmintic [27], osteogenic activity [43]. This review article focuses on recent applications of Claisen-Schmidt condensation reaction employed in the synthesis of chalcone, its transformation to heterocyclic compounds and pharmacological activities.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Chalcones: Synthesis, Transformation and Pharmacological Activities

Ovonramwen

Owolabi

Oviawe

2019

AJOCS

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Chalcones are useful intermediates in the synthesis of heterocyclic compound and the unique reagents in organic synthesis. The usual approach to obtain chalcones is through Claisen-Schmidt condensation. Several novel heterocyclic chalcone analogs have emerged. Chalcones are multifunctional molecules that possess promising pharmacological activities. Chalcones are known for anti-cancer, antioxidant, anti-inflammatory, anti-microbial, anti-tubercular, antileishmanial, antimalarial, anthelmintic, osteogenic activities. This review article focuses on recent applications of Claisen-Schmidt condensation reaction employed in the synthesis of chalcone, its transformation to heterocyclic compounds and pharmacological activities.

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Synthesis and biological evaluation of chalcones as potential antileishmanial agents

Cited by 38 publications

References 34 publications

Cinnamic Acid Bornyl Ester Derivatives from Valeriana wallichii Exhibit Antileishmanial In Vivo Activity in Leishmania major-Infected BALB/c Mice

Cinnamic Acid Bornyl Ester Derivatives from Valeriana wallichii Exhibit Antileishmanial In Vivo Activity in Leishmania major-Infected BALB/c Mice

Synthesis of the Proposed Structure of Damaurone D and Evaluation of Its Anti-inflammatory Activity

Recent Advances in Chalcones: Synthesis, Transformation and Pharmacological Activities

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