Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity

D’hooghe, Matthias; Vandekerckhove, Stéphanie; Mollet, Karen; Vervisch, Karel; Dekeukeleire, S.; Lehoucq, Liesbeth; Lategan, Carmen; Smith, Peter J.; Chibale, Kelly; Kimpe, Norbert De

doi:10.3762/bjoc.7.205

Cited by 28 publications

(11 citation statements)

References 39 publications

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“…1,2,3-Triazoles are very important heterocycles showing excellent bioactivities in pharmaceutical and agrochemical applications. Compounds containing 1,2,3-triazoles have been reported for their antifungal [21,22,23], antibacterial [24,25,26,27], anti-HIV [28], insecticidal [29], herbicidal [30], antiviral [31], antitumor [32], tuberculosis inhibitory [33], antiprotozoal [34], antimalarial [35], anticancer [36], and larvicidal [37] activities. The fungicidal activity of the commercial fungicide fluconazole can be improved by introducing a 1,2,3-triazole moiety into the molecule [38,39].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Benzamidine Derivatives Carrying 1,2,3-Triazole Moieties

et al. 2014

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Eighteen novel benzamidine derivatives containing 1,2,3-triazole moieties were synthesized. The in vitro and in vivo fungicidal acitivities of the title compounds and the arylamidine intermediates against Colletotrichum lagenarium and Botrytis cinerea were tested. The synthesized benzamidines exhibited weak antifungal activities in vitro against the tested fungi, but some of the compounds showed excellent activities in vivo to the same strains. Among the compounds tested, 9b showed 79% efficacy in vivo against C. lagenarium at a concentration of 200 μg/mL, and the efficacy of compound 16d (90%) toward the same strain was even superior than that of the commercial fungicide carbendazim (85%).

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Benzamidine Derivatives Carrying 1,2,3-Triazole Moieties

et al. 2014

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“…(2010) and Kobarfard et al. (2012) , respectively, among other studies ( Robin et al., 2007 , Dhooghe et al., 2011 ). However, there are only a few examples of the γ-amino alcohol moiety reported in the last thirteen years ( Dhooghe et al., 2009 , Perez-Silanes et al., 2009 , Mendoza et al., 2011 , Quiliano and Aldana, 2013 ).…”

Section: Introductionmentioning

confidence: 62%

Exploring the scope of new arylamino alcohol derivatives: Synthesis, antimalarial evaluation, toxicological studies, and target exploration

Quiliano¹,

Mendoza²,

Fong³

et al. 2016

International Journal for Parasitology: Drugs and Drug Resistan

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Synthesis of new 1-aryl-3-substituted propanol derivatives followed by structure-activity relationship, in silico drug-likeness, cytotoxicity, genotoxicity, in silico metabolism, in silico pharmacophore modeling, and in vivo studies led to the identification of compounds 22 and 23 with significant in vitro antiplasmodial activity against drug sensitive (D6 IC50 ≤ 0.19 μM) and multidrug resistant (FCR-3 IC50 ≤ 0.40 μM and C235 IC50 ≤ 0.28 μM) strains of Plasmodium falciparum. Adequate selectivity index and absence of genotoxicity was also observed. Notably, compound 22 displays excellent parasitemia reduction (98 ± 1%), and complete cure with all treated mice surviving through the entire period with no signs of toxicity. One important factor is the agreement between in vitro potency and in vivo studies. Target exploration was performed; this chemotype series exhibits an alternative antimalarial mechanism.

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“…One of the possible pathways to overcome these drawbacks is to functionalize F. The Huisgen 1,3‐dipolar cycloaddition of alkynes and azides is known to result in the formation of 1,2,3‐triazole moiety which has been found to be effective as an essential pharmacophore in medicinal chemistry . Many of the triazole‐containing molecules were demonstrated to exhibit anti‐HIV, anti‐cancer, antibacterial, antifungal and antimalarial properties . Thus, transformation of F into triazole‐containing molecules is a straightforward method which can have potential applications in therapeutics.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐Proliferative Activity of a Triazole‐Fused Thymidine Analogue

et al. 2020

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Here we report the synthesis of two-an acyclic and a macrocyclic-analogues of thymidine linked to a triazole moiety. The new molecules were synthesized through an intramolecular 1,3-dipolar cycloaddition reaction of the diazido derivative of thymidine with a suitable alkyne. The acyclic nucleoside showed dose dependent cytotoxicity against glioblastoma and breast cancer cells by causing significant cellular damage as studied with confocal laser scanning microscopy. In silico induced fit molecular docking studies showed poly(ADP-ribose) polymerase 1 (PARP1) as a potential target of the acyclic nucleoside. On the other hand, both the analogues showed no toxicity against normal fibroblast cells. ChemistrySelectCommunications

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Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity

Cited by 28 publications

References 39 publications

Synthesis and Antifungal Activity of Benzamidine Derivatives Carrying 1,2,3-Triazole Moieties

Synthesis and Antifungal Activity of Benzamidine Derivatives Carrying 1,2,3-Triazole Moieties

Exploring the scope of new arylamino alcohol derivatives: Synthesis, antimalarial evaluation, toxicological studies, and target exploration

Synthesis and Anti‐Proliferative Activity of a Triazole‐Fused Thymidine Analogue

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