1<i>H</i>-1,2,3-Triazole-Tethered Isatin–Ferrocene and Isatin–Ferrocenylchalcone Conjugates: Synthesis and in Vitro Antitubercular Evaluation

Kumar, Kapil; Carrère-Kremer, Séverine; Kremer, Laurent; Guérardel, Yann; Biot, Christophe; Kumar, Vipan

doi:10.1021/om301157z

Cited by 91 publications

(37 citation statements)

References 56 publications

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“…Recent disclosure from our group has shown the synthesis of 1 H ‐1,2,3‐triazole‐tethered β‐lactam‐ferrocene and β‐lactam‐ferrocenylchalcone hybrids along with the evaluation of their antitubercular activities [20]. The methodology was further developed toward the synthesis of 1 H ‐1,2,3‐triazole‐linked isatin‐ferrocene and isatin‐ferrocenylchalcone conjugates with a further extension to include spiro‐isatin in these molecular conjugates along with their evaluation against M. tuberculosis [21]. Continuing with our efforts, the present article describes the synthesis of uracil‐ferrocene and uracil‐ferrocenylchalcone conjugates, linked via 1 H ‐1,2,3‐triazole functionality (as shown in Figure ), along with their antitubercular evaluation.…”

Section: Introductionmentioning

confidence: 99%

1H‐1,2,3‐triazole‐tethered uracil‐ferrocene and uracil‐ferrocenylchalcone conjugates: Synthesis and antitubercular evaluation

et al. 2016

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Copper-catalyzed azide-alkyne [3 + 2] cycloaddition has been utilized for preparing a series of 1H-1,2,3-triazoles with the purpose of probing structure-activity relationships among a uracil-ferrocene-triazole conjugate family. The antitubercular evaluation studies revealed an improvement in activity with the introduction of a ferrocene nucleus among N-alkylazido-uracil precursors, with a preference for a bromo-substituent along with moderate chain lengths of n = 2-6. The reported protocol is a successful approach for integrating uracil-ferrocene-chalcone functionalities tethered via 1H-1,2,3-triazole rings with apparent physicochemical stability.

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Section: Introductionmentioning

confidence: 99%

1H‐1,2,3‐triazole‐tethered uracil‐ferrocene and uracil‐ferrocenylchalcone conjugates: Synthesis and antitubercular evaluation

et al. 2016

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“…Insertion of of triazole moiety into the N ‐n‐hexyl‐ N ‐phenylanilinochalcone dendritic structure would enhance the biological properties . The synthetic pathway leading to N ‐n‐hexyl‐ N ‐phenylanilinochalcone dendrimers incorporating triazole moiety is shown in Scheme .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Photophysical, Electrochemical Properties and Anticancer, Antimicrobial Activity of N -n-Hexyl-N -Phenylanilinochalcone-Capped Dendrimers

Ravivarma

Rajakumar

2017

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Dendrimers with N‐n‐hexyl‐N‐phenylanilinochalcone as surface group and triazole as bridging unit were synthesized in good yields. UV‐Visible absorption spectrum of N‐n‐hexyl‐N‐phenylanilinocalcone dendrimers show two intense absorption bands at 277–297 and 419 nm and the molar extinction coefficient of the dendrimers increases with increase in the dendrimer generation. In emission spectrum, the chalcone dendrimers show a red shift of 10 nm for the first generation dendrimers when compared to the corresponding zeroth generation dendrimers. In cyclic voltammogram, all the dendrimers show quasi‐reversible redox peaks. N‐n‐Hexyl‐N‐Phenylanilinochalcone dendrimers show better cell viability (≈55%) even at higher concentration against normal liver cell line. The cytotoxicity of the chalcone dendrimers were carried out on A549 lung adenocarcinoma cell lines at various concentrations. The cytotoxicity of the chalcone dendrimers was found to be dose dependent. The higher generation fluorene and benzene core chalcone dendrimers with more number of chalcone units show significant anticancer activity. Interestingly, all the chalcone dendrimers exhibit significant antimicrobial activity against the tested pathogenic microbes.

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“…Continuing with our efforts in the synthesis of novel molecular conjugates with biological potential (Raj et al, 2013c;Raj et al, 2013a;Nisha et al, 2013;Kumar et al, 2013;Kumar et al 2012), we recently discussed the synthesis of 1H-1,2,3-triazole-tethered b-lactam-isatin conjugates and their in vitro evaluation against T. vaginalis Raj et al, 2013b). Most of the synthesized compounds exhibited 100 % growth inhibition at 100 lM with the most potent and non-cytotoxic compound (Fig.…”

Section: Introductionmentioning

confidence: 92%

Synthesis and preliminary in vitro activity of mono- and bis-1H-1,2,3-triazole-tethered β-lactam–isatin conjugates against the human protozoal pathogen Trichomonas vaginalis

et al. 2014

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Synthesis and preliminary in vitro activity of monoand bis-1H-1,2,3-triazole-tethered b-lactam-isatin conjugates against the human protozoal pathogen Trichomonas vaginalis Abstract In this study, we describe the synthesis of mono-and bis-1H-1,2,3-triazole-tethered b-lactam-isatin conjugates using copper-catalysed azide-alkyne cycloaddition reaction between mono-and di-propargylated azetidin-2-ones and N-alkylazido isatins. The synthesized conjugates were evaluated for their preliminary in vitro analysis against Trichomonas vaginalis at 50 lM. The efficacy of synthesized hybrids was observed to depend on the substituent at N-1 position of b-lactam ring, as well as the presence of single/double 1H-1,2,3-triazole linker. Among the synthesized conjugates, the presence of a ptolyl substituent at N-1 of b-lactam ring was preferred for good activity profiles while the increase in spacer length did not influence the efficacy of the compounds. Compounds with high levels of potency were further analysed to determine their IC 50 values, as well as cytotoxicity profiles against mammalian cells. The most active compound in the synthesized conjugates displayed an IC 50 value of 10.49 lM against cultured G3 strain of T. vaginalis and was non-toxic to cultured mammalian HeLa cells at the same concentration.

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1H-1,2,3-Triazole-Tethered Isatin–Ferrocene and Isatin–Ferrocenylchalcone Conjugates: Synthesis and in Vitro Antitubercular Evaluation

Cited by 91 publications

References 56 publications

1H‐1,2,3‐triazole‐tethered uracil‐ferrocene and uracil‐ferrocenylchalcone conjugates: Synthesis and antitubercular evaluation

1H‐1,2,3‐triazole‐tethered uracil‐ferrocene and uracil‐ferrocenylchalcone conjugates: Synthesis and antitubercular evaluation

Synthesis, Photophysical, Electrochemical Properties and Anticancer, Antimicrobial Activity of N -n-Hexyl-N -Phenylanilinochalcone-Capped Dendrimers

Synthesis and preliminary in vitro activity of mono- and bis-1H-1,2,3-triazole-tethered β-lactam–isatin conjugates against the human protozoal pathogen Trichomonas vaginalis

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