Microwave assisted regioselective synthesis of quinoline appended triazoles as potent anti-tubercular and antifungal agents via copper (I) catalyzed cycloaddition

Nesaragi, Aravind R.; Kamble, Ravindra R.; Bayannavar, Praveen K.; Shaikh, Saba Kauser J.; Hoolageri, Swati R.; Kodasi, Barnabas; Joshi, Shrinivas D.; Kumbar, Vijay

doi:10.1016/j.bmcl.2021.127984

Cited by 49 publications

(18 citation statements)

References 26 publications

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“…The starting materials and solvents used in the present work have been purchased commercially. The reactions according to Scheme 1 [4,5] were monitored by TLC plates procured from Sigma-Aldrich. Melting point of the title compound 2PPT has been recorded on electric melting point apparatus and uncorrected.…”

Section: Methodsmentioning

confidence: 99%

“…Organic scaffolds containing 1,2,4-triazole moiety have been investigated for their outstanding activities such as antihypertensive, antiviral, and anticancer, etc. and hence, they have established themselves as important pharmacophores [1][2][3][4][5]. In this study, we have synthesized a 1,2,4-triazole containing molecule linked with ethynyl end (2PPT), which is a possible synthon for carrying out interesting cycloaddition reactions [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

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X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone

et al. 2021

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This study is composed of X-ray diffraction and Density Functional Theory (DFT) based molecular structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one (2PPT). Crystal data for C11H9N3O: Monoclinic, space group P21/c (no. 14), a = 7.8975(2) Å, b = 11.6546(4) Å, c = 11.0648(3) Å, β = 105.212(2)°, V = 982.74(5) Å3, Z = 4, T = 296.15 K, μ(MoKα) = 0.091 mm-1, Dcalc = 1.346 g/cm3, 13460 reflections measured (5.174° ≤ 2Θ ≤ 64.72°), 3477 unique (Rint = 0.0314, Rsigma = 0.0298) which were used in all calculations. The final R1 was 0.0470 (I > 2σ(I)) and wR2 was 0.1368 (all data). The experimentally determined data was supported by theoretically optimized calculations processed with the help of Hartree-Fock (HF) technique and Density Functional Theory with the 6-311G(d,p) basis set in the ground state. Geometrical parameters (Bond lengths and angles) as well as spectroscopic (FT-IR, 1H NMR, and 13C NMR) properties of 2PPT molecule has been optimized theoretically and compared with the experimentally obtained results. Hirshfeld surface analysis with 2D fingerprinting plots was used to figure out the possible and most significant intermolecular interactions. The electronic characterizations such as molecular electrostatic potential map (MEP) and Frontier molecular orbital (FMO) energies have been studied by DFT/B3LYP approach. The MEP imparted the detailed information regarding electronegative and electropositive regions across the molecule. The HOMO-LUMO energy gap as high as 5.3601 eV was found to be responsible for the high kinetic stability of the 2PPT.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone

et al. 2021

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“…-Quinoline Hybrids. Nesaragi et al [116] described a new sequence of quinolin-3-yl-methyl-1,2,3triazolyl-1,2,4-triazol-3(4H)-ones synthesized via click chemistry as a final tactic in which azides with final alkynes were tested for antifungal properties against four various pathogenic fungi (C. albicans, A. flavus, A. fumigatus, and A. niger). Fluconazole was employed as a standard drug.…”

Section: 23-triazolementioning

confidence: 99%

A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR)

Marzi

Farjam

Kazeminejad

et al. 2022

Journal of Chemistry

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A pharmacophore system has been found as 1,2,3-triazole, a five-membered heterocycle ring with nitrogen heteroatoms. These heterocyclic compounds can be produced using azide-alkyne cycloaddition processes catalyzed by ruthenium or copper. The bioactive compounds demonstrated antitubercular, antibacterial, anti-inflammatory, anticancer, antioxidant, antiviral, and antidiabetic properties. This heterocycle molecule, in particular, with one or more 1,2,3-triazole cores has been found to have the most powerful antifungal effects. The goal of this review is to highlight recent developments in the synthesis and structure-activity relationship (SAR) investigation of this prospective fungicidal chemical. Also there have been explained drugs and mechanism of action of a triazole compound with antifungal activity. This review will be useful in a variety of fields, including medicinal chemistry, organic chemistry, mycology, and pharmacology.

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“…[25][26][27] N-Arylsydnone acts as a novel and functional pioneer for the synthesis of varied biologically functional heterocycles viz., pyrazoles, 1,3,4-oxadiazoles, phenyl indazoles, pyrazolines, and tetrazines via 1,3-dipolar cycloaddition and addition elimination reactions. [28] Hence, we synthesized 1,2,4-triazole by using Narylsydnone that belongs to mesoionic class of compounds.…”

Section: Chemistryselectmentioning

confidence: 99%

Green Synthesis of Novel Triazolothiadiazine‐Coumarins Catalyzed by Agro Waste Extract: An Approach towards In‐Silico and In‐Vitro Anti‐Fungal Activity

et al. 2022

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A green, commodious, immensely versatile synthetic route for agro waste extract WELPSA catalyzed cyclocondensation of biologically active triazolothiadiazine‐coumarin hybrid derivatives has been studied. A proficient synthesis offused heterocycles 9 i–wvia dehydrative condensation with cyclization of4‐((4‐amino‐5‐mercapto‐4H‐1,2,4‐triazol‐3‐yl)methyl)‐2‐aryl‐2,4‐dihydro‐3H‐1,2,4‐triazol‐3‐one (5 a‐‐c) and substituted bromoacyl coumarins (8 d‐‐h)has been incorporated in presence of different catalysts including WELPSA, a green catalyst. The in silico docking studies of these previously unknown compounds revealed favorable C score and Chemscore values and the in vitro antifungal assay against three fungal strains showed excellent to good activity.

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Microwave assisted regioselective synthesis of quinoline appended triazoles as potent anti-tubercular and antifungal agents via copper (I) catalyzed cycloaddition

Cited by 49 publications

References 26 publications

X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone

X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone

A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR)

Green Synthesis of Novel Triazolothiadiazine‐Coumarins Catalyzed by Agro Waste Extract: An Approach towards In‐Silico and In‐Vitro Anti‐Fungal Activity

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