Synthesis by microwave-assisted 1,3-dipolar cycloaddition of 1,2,3-triazole 1′-homo-3′-isoazanucleosides and evaluation of their anticancer activity

Costa, Joana; Garcı́a-Mera, Xerardo; Caamaño, Olga; Brea, José; Loza, Marı́a Isabel

doi:10.1016/j.ejmech.2015.05.029

Cited by 13 publications

(3 citation statements)

References 47 publications

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“…Literature survey highlights that 1,2,3‐triazole‐based heterocyclic scaffolds possess a wide array of pharmacological activities including antimicrobial, [ 28 ] antiproliferative, [ 29 ] antitubercular, [ 30 ] anti‐HIV, [ 31 ] antibacterial, [ 32 ] anticancer, [ 33 ] and so on. Furthermore, the functionalization of heterocyclic scaffolds with different groups has been a successful strategy to improve the physical properties as well as biological activities of drug molecules.…”

Section: Introductionmentioning

confidence: 99%

“…[25][26][27] Therefore, the design of high affinity, isozymeselective inhibitors devoid of causing side effects due to off-target CA modulation would be a fruitful and effective strategy for the development of potent therapeutic agents. [2] Literature survey highlights that 1,2,3-triazole-based heterocyclic scaffolds possess a wide array of pharmacological activities including antimicrobial, [28] antiproliferative, [29] antitubercular, [30] anti-HIV, [31] antibacterial, [32] anticancer, [33] and so on. Furthermore, the functionalization of heterocyclic scaffolds with different groups has been a successful strategy to improve the physical properties as well as biological activities of drug molecules.…”

Section: Introductionmentioning

confidence: 99%

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Benzenesulfonamides with trisubstituted triazole motif as selective carbonic anhydrase I, II, IV, and IX inhibitors

Sharma

Kumar

Angeli

et al. 2022

Archiv der Pharmazie

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Twenty novel 1,2,3-triazole benzenesulfonamides featuring nitrile 8a-g, carbothioamide 9a-f, and N′-hydroxycarboximidamide 10a-g functionalities were designed and synthesized to improve potency and selectivity as carbonic anhydrase inhibitors (CAIs). The synthesized 1,2,3-triazole compounds were tested in vitro as CAIs against four physiologically and pharmacologically relevant isoforms of human carbonic anhydrase (hCA I, II, IV, and IX). Compounds 8a-g, 9a-f, and 10a-g displayed variable inhibition constants ranging from 8.1 nM to 3.22 μM for hCA I, 4.7 nM to 0.50 μM for hCA II, 15.0 nM to 3.7 μM for hCA IV, and 29.6 nM to 0.27 μM for hCA IX. As per the inhibition data profile, compounds 9a-e exhibited strong efficacy for hCA IV, whereas the inhibition was found to be somewhat

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Benzenesulfonamides with trisubstituted triazole motif as selective carbonic anhydrase I, II, IV, and IX inhibitors

Sharma

Kumar

Angeli

et al. 2022

Archiv der Pharmazie

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“…The required reaction medium must have environmentally benign criteria such as non-toxicity, biodegradability, availability, recyclability and also in economically beneficial among others. However, interesting green protocols have been reported in the literature for the synthesis of heterocyclic compounds through multicomponent reaction including microwave assisted [23], solid support and montmorillonite clay catalyzed [24, 25], ultrasonic triggered [26], and with different class of eutectic mixture solvent mediated synthesis [27, 28]. Among the various green protocols, room temperature eutectic mixtures are perspective and effective method for chemical transformations.…”

Section: Introductionmentioning

confidence: 99%

An expeditious and environmentally benign synthesis of dispiro-3-phenylpyrrolothiazoles in ACI/EG eutectic mixture and its antioxidant and antimicrobial activities against urinary tract pathogens

et al. 2019

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The present study reveals the robust and facile methodology for the synthesis of massively selective dispiro-3-phenylpyrrolothiazole hybrids via one-pot 1,3-dipolar cycloaddition reaction by environmentally supported solvents and to evaluate their biological activities. The quaternary ammonium salt eutectic mixture, acetylcholine iodide-ethylene glycol (ACI/EG) medium brings an efficient environment for the synthesis of dispiropyrrolothiazole with excellent yield in shorter reaction time than imidazolium ionic liquids. The eutectic mixture was recovered and reused without any significant drop in their catalytic activity. Among the eight synthesized compounds 4a–h , halogen derivatives are exhibiting significant antimicrobial activities against selected uropathogens pathogens. Interestingly, chloro and bromo derivatives exhibits the minimum inhibitory concentration (MIC) of 12.5 μg/ml and 6.25 μg/ml towards Escherichia coli, Klebsiella pneumonia, and Staphylococcus aureus respectively. In addition, the IC 50 values of DPPH radicals with synthesized compounds are interesting, particularly compounds 4a , 4d and 4e shows lower than the control BHA indicating their potent scavenging ability of free radicals. Electronic supplementary material The online version of this article (10.1186/s13065-019-0553-3) contains supplementary material, which is available to authorized users.

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ChemInform Abstract: Synthesis by Microwave‐Assisted 1,3‐Dipolar Cycloaddition of 1,2,3‐Triazole 1′‐Homo‐3′‐isoazanucleosides and Evaluation of Their Anticancer Activity.

et al. 2015

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Synthesis by Microwave-Assisted 1,3-Dipolar Cycloaddition of 1,2,3-Triazole 1'-Homo-3'-isoazanucleosides and Evaluation of Their Anticancer Activity. -Racemic isoazanucleosides (III) are synthesized by microwave-assisted 1,3-dipolar cycloaddition of proline derivative (I) with various alkynes. The compounds (IIId,e) show significant cytotoxic activity against different human carcinoma cell lines. -(FERREIRA DA COSTA, J.; GARCIA-MERA, X.; CAAMANO*, O.; BREA, J. M.; LOZA, M. I.; Eur. J. Med. Chem. 98 (2015) 212-220, http://dx.

show abstract

Synthesis by microwave-assisted 1,3-dipolar cycloaddition of 1,2,3-triazole 1′-homo-3′-isoazanucleosides and evaluation of their anticancer activity

Cited by 13 publications

References 47 publications

Benzenesulfonamides with trisubstituted triazole motif as selective carbonic anhydrase I, II, IV, and IX inhibitors

Benzenesulfonamides with trisubstituted triazole motif as selective carbonic anhydrase I, II, IV, and IX inhibitors

An expeditious and environmentally benign synthesis of dispiro-3-phenylpyrrolothiazoles in ACI/EG eutectic mixture and its antioxidant and antimicrobial activities against urinary tract pathogens

ChemInform Abstract: Synthesis by Microwave‐Assisted 1,3‐Dipolar Cycloaddition of 1,2,3‐Triazole 1′‐Homo‐3′‐isoazanucleosides and Evaluation of Their Anticancer Activity.

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