Synthesis of 1H-1,2,3-triazole linked β-lactam–isatin bi-functional hybrids and preliminary analysis of in vitro activity against the protozoal parasite Trichomonas vaginalis

Raj, Raghu; Singh, Pardeep; Haberkern, Nathan T.; Faucher, Ryan M.; Patel, Neal M.; Land, Kirkwood M.; Kumar, Vipan

doi:10.1016/j.ejmech.2013.03.019

Cited by 38 publications

(13 citation statements)

References 46 publications

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“…30–31 The synthesized conjugates proved to be potent against T. vaginalis exhibiting IC 50 values below 10 μM along with minimal cytotoxicity to cultured human cells. The methodology was further extended towards synthesis of N -propargylated-isatin Mannich adducts along with their in vitro evaluation against T. vaginalis and T. foetus with the most potent compound exhibiting an IC 50 value of 11.3 μM against T. foetus .…”

Section: Introductionmentioning

confidence: 98%

Design, synthesis and preliminary antimicrobial evaluation of N-alkyl chain-tethered C-5 functionalized bis-isatins

et al. 2017

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A series of N-alkyl tethered C-5 functionalized bis-isatins were synthesized and evaluated for antimicrobial activity against pathogenic microorganisms. The preliminary evaluation studies revealed the compound 4t, with an optimal combination of bromo-substituent at the C-5 position of isatin ring along with propyl chain linker being most active among the synthesized series exhibiting an IC50 value of 3.72 μM against Trichomonas vaginalis while 4j exhibited an IC50 value of 14.8 μM against Naegleria fowleri, more effective than the standard drug Miltefosine. The compound 3f with an octyl spacer length was the most potent among the series against Giardia lamblia with an IC50 of 18.4 μM while 3d exhibited an IC50 of 23 μM against Entamoeba histolytica. This library was also screened against the fungal pathogen Aspergillus parasiticus. A number of the compounds demonstrated potency against this fungus, illustrating a possible broad-spectrum activity. Furthermore, an evaluation of these synthesized compounds against a panel of normal flora bacteria revealed them to be non-cytotoxic, demonstrating the selectivity of these compounds. This observation, in combination with previous studies that isatin is non-toxic to humans, presents a new possible scaffold for drug discovery against these important protozoal pathogens of humans and animals.

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Section: Introductionmentioning

confidence: 98%

Design, synthesis and preliminary antimicrobial evaluation of N-alkyl chain-tethered C-5 functionalized bis-isatins

et al. 2017

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“…In continuation with our interest towards the synthesis of novel molecular frameworks having biological relevance [25], we recently disclosed the synthesis of 1H-1,2,3-triazole-tethered isatin-b-lactam conjugates along with the preliminary analysis of their in vitro activity against Trichomonas vaginalis at 10 and 100 mM [26]. Eighteen of the synthesized hybrids have shown 100% growth inhibition at 100 mM with the most potent and non-cytotoxic compound showing and IC 50 of 7.69 mM.…”

Section: Introductionmentioning

confidence: 99%

N-Propargylated isatin-Mannich mono- and bis-adducts: Synthesis and preliminary analysis of in vitro activity against Tritrichomonas foetus

Nisha

Kumar

Bhargava

et al. 2014

European Journal of Medicinal Chemistry

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Cu(I)Cl promoted synthesis of N-propargylated-isatin Mannich mono- and bis-adducts with an extension towards the synthesis of N-propargylated-isatin-7-chloroquinoline conjugates was described. The synthesized scaffolds were evaluated for their in vitro activity against the veterinary protozoal pathogen Tritrichomonas foetus and cytotoxicity against human prostate (PC-3) cancer cell line. The preliminary evaluation data revealed the enhancement in the activity profiles with the introduction of 7-chloroquinoline ring with the most active conjugates 7a, 7c and 7d exhibiting an IC₅₀ of 22.2, 11.3 and 24.5 μM respectively against T. foetus and minimal toxicity against human prostate (PC-3) cell lines.

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“…There are some reports of b-lactam-azole hybrid displaying good antimicrobial activities (Kumar et al, 2012;Raj et al, 2013;Vatmurge et al, 2008). Based on these observations and in continuation of our interest for the synthesis of new bioactive b-lactams, we report herein the synthesis of some novel b-lactam-triazole hybrids and their in vitro antibacterial, antifungal and antimalarial evaluation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of some new β-lactam-triazole hybrids

et al. 2015

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A series of novel b-lactams was synthesized from different imines and a special ketene derived from Nendo-5-norbornene-2,3-dicarboxyloylglycine 1 via the [2 ? 2] ketene imine cycloaddition. Then, b-lactams 3a-h were treated with 1-azido-4-nitrobenzene 4 to afford blactam-triazole hybrids 5a-h. Of the twenty-three b-lactams tested against chloroquine-resistant P. falciparum K14 strain, 3a and 3d showed IC 50 \ 20 lM, while 3j, 3m, 5a-5f exhibited IC 50 \ 50. These newly synthesized blactams were also tested against S. aureus, E. coli, P. aeruginosa, C. albicans and C. glabrata and showed no activity below 125 lg/mL.

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Synthesis of 1H-1,2,3-triazole linked β-lactam–isatin bi-functional hybrids and preliminary analysis of in vitro activity against the protozoal parasite Trichomonas vaginalis

Cited by 38 publications

References 46 publications

Design, synthesis and preliminary antimicrobial evaluation of N-alkyl chain-tethered C-5 functionalized bis-isatins

Design, synthesis and preliminary antimicrobial evaluation of N-alkyl chain-tethered C-5 functionalized bis-isatins

N-Propargylated isatin-Mannich mono- and bis-adducts: Synthesis and preliminary analysis of in vitro activity against Tritrichomonas foetus

Synthesis and biological evaluation of some new β-lactam-triazole hybrids

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