A click chemistry approach for the synthesis of cyclic ureido tethered coumarinyl and 1-aza coumarinyl 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis H37Rv and their in silico studies

Khanapurmath, Netravati; Kulkarni, Manohar V.; Joshi, Shrinivas D.; Kumar, Gourav

doi:10.1016/j.bmc.2019.115054

Cited by 14 publications

(6 citation statements)

References 47 publications

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“…The ATR-IR spectra of the complexes showed a strong band at ca. 1717−1732 and 1547−1562 cm −1 pertaining to the stretching vibrations of lactonic CO 22 and azole CN groups, respectively. Alongside this, in the cases of acetate complexes, a shoulder band around 1730 cm −1 observed was ascribed to the stretching vibrations of the acetate carbonyl module.…”

Section: Resultsmentioning

confidence: 99%

Novel Carbene Anchored Molecular Catalysts for Hydrogen Evolution Reactions

et al. 2021

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The development of low-cost molecular electrocatalysts for the HER from water remains scarce. The efficient electrocatalytic hydrogen evolution reactions (HER) with a series of sterically encumbered carbene ligated silver(I), gold(I) and nickel(II) complexes established here demonstrate the potential of molecular catalyst in hydrogen production from water. Tuning the benzannulation on the coumarin-substituted N-heterocyclic carbene (NHC) ligands afforded six new silver(I) (5–10), two new gold(I) (11 and 12), and two reported nickel(II) (13 and 14) NHC complexes, which differ by the steric bulk around the metal atom and the counterion. Benefiting from the desirable structure and appropriate porous morphology, complexes 6, 9, 10, and 11 exhibited significant electrocatalytic HER activity in acidic medium with an overpotential of −226.4, −445, −243 and −310 mV vs RHE, respectively, to drive a current density of 10 mA/cm2 when immobilized on glassy carbon electrode, which is analogous to that of several transition metal-based nanomaterials. The kinetic parameters such as Tafel slope value and exchange current density for the active complexes and the former observation authenticated the Volmer–Heyrovsky mechanism. Theoretical studies advocate the potential of developing novel series of carbene-ligated HER electrocatalysts based on the controlled ligand field following scalable and viable protocols.

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Section: Resultsmentioning

confidence: 99%

Novel Carbene Anchored Molecular Catalysts for Hydrogen Evolution Reactions

et al. 2021

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“…The docking study revealed an additional interaction of bezimidazolone oxygen, which made compounds 2.159 conformationally more flexible (Scheme 2.31). 48…”

Section: Scheme 230mentioning

confidence: 99%

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Pathak¹,

Pan²

2022

Arkivoc

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A typical 1,2,3-triazoles are important aromatic heterocyclic compounds with three adjacent nitrogen atoms. These "unnatural" heterocycles found applications in pharmaceutical science, material science and chemical biology. Oligo-1,2,3-triazole linked molecules showed interesting applications in the field of DNA binding, selfassembly, surface modification, supramolecular chemistry etc. In this article, oligo-1,2,3-triazoles are broadly classified into two categories: (i) 1,2,3-triazoles are connected through varieties of organic molecules and (ii) triazole units are connected with one another either by N-(CH)n-C linkages or by amide bonds generated from amino acids. Syntheses and properties of some of these oligomers are reviewed in this article.

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“…Scientists who have been able to synthesize new vinyl sulfones based on triazole and its allyl isomer (Doherty et al, 2017), as well as a series of new derivatives of 4-(azidomethyl)-2H-chromen-2-ones active against Mycobacterium tuberculosis, are searching for new promising anti-TB molecules among triazole derivatives (Khanapurmath et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Toxicity parameters of a new 1,2,4-triazole derivative when subcutaneously injected to guinea pigs

Zazharskyi,

Bigdan,

Parchenko

et al. 2024

Regul. Mech. Biosyst.

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The results of the literature analysis indicate a wide spectrum of biological activity of 1,2,4-triazole derivatives. Low toxicity, reactivity, and high biological activity of 1,2,4-triazole derivatives make this class of compounds very attractive. The obtained data determine the relevance of further studies of 1,2,4-triazole derivatives to find new highly effective biologically active substances that can become the basis for new medicines. Our further work aimed to study some toxicity parameters of 3-(3-fluorophenyl)-6-(4-methoxyphenyl)-7H-[1,2,4]-triazolo-[3,4-b][1,3,4] thiadiazine when administered subcutaneously to guinea pigs, which is a necessary condition for further implementation in practice of this compound. In this work, we observed an absence of toxic effects after a single subcutaneous injection to guinea pigs at a dose of 40 mg/kg experimental drug. The results of macro- and microscopic examinations of internal organs 14 days after a single subcutaneous injection of the studied compound at a dose of 20, 40 mg/kg showed the absence of any anatomical and morphological disorders in the tissue structures of guinea pigs. The calculated value indicates a high degree of safety of 3-(3-fluorophenyl)-6-(4-methoxyphenyl)-7H-[1,2,4]-triazolo-[3,4-b][1,3,4] thiadiazine and its prospects for use in veterinary practice as an effective and safe tuberculocidal agent.

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A click chemistry approach for the synthesis of cyclic ureido tethered coumarinyl and 1-aza coumarinyl 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis H37Rv and their in silico studies

Cited by 14 publications

References 47 publications

Novel Carbene Anchored Molecular Catalysts for Hydrogen Evolution Reactions

Novel Carbene Anchored Molecular Catalysts for Hydrogen Evolution Reactions

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Toxicity parameters of a new 1,2,4-triazole derivative when subcutaneously injected to guinea pigs

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