Synthesis and discovery of triazolo-pyridazine-6-yl-substituted piperazines as effective anti-diabetic drugs; evaluated over dipeptidyl peptidase-4 inhibition mechanism and insulinotropic activities

Bindu, B.; Vijayalakshmi, S.

doi:10.1016/j.ejmech.2019.111912

Cited by 17 publications

(7 citation statements)

References 33 publications

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“…In 2020, Manikandan and co-workers opted for the use of 2-MeTHF in the synthesis of a triazolo-pyridazine-6-yl-substituted via a Buchwald-Hartwig cross-coupling. 283 The 2-MeTHF was used as the solvent in the final stage of the synthesis for 12 medicinally relevant antidiabetic compounds, and yields were reported in the range of 92–98% using a catalytic combination of 10 mol % Pd 2 (dba) 3 /XPhos, in the presence of NaO t Bu at room temperature for 4 h, see Scheme 27 .…”

Section: Common Reactions In Dipolar Aprotic or Ethereal Solvents Rep...mentioning

confidence: 99%

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

et al. 2022

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Dipolar aprotic and ethereal solvents comprise just over 40% of all organic solvents utilized in synthetic organic, medicinal, and process chemistry. Unfortunately, many of the common “go-to” solvents are considered to be “less-preferable” for a number of environmental, health, and safety (EHS) reasons such as toxicity, mutagenicity, carcinogenicity, or for practical handling reasons such as flammability and volatility. Recent legislative changes have initiated the implementation of restrictions on the use of many of the commonly employed dipolar aprotic solvents such as dimethylformamide (DMF) and N -methyl-2-pyrrolidinone (NMP), and for ethers such as 1,4-dioxane. Thus, with growing legislative, EHS, and societal pressures, the need to identify and implement the use of alternative solvents that are greener, safer, and more sustainable has never been greater. Within this review, the ubiquitous nature of dipolar aprotic and ethereal solvents is discussed with respect to the physicochemical properties that have made them so appealing to synthetic chemists. An overview of the current legislative restrictions being imposed on the use of dipolar aprotic and ethereal solvents is discussed. A variety of alternative, safer, and more sustainable solvents that have garnered attention over the past decade are then examined, and case studies and examples where less-preferable solvents have been successfully replaced with a safer and more sustainable alternative are highlighted. Finally, a general overview and guidance for solvent selection and replacement are included in the Supporting Information of this review.

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Section: Common Reactions In Dipolar Aprotic or Ethereal Solvents Rep...mentioning

confidence: 99%

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

et al. 2022

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“…The antitumor properties of 1,2,4‐Triazolo[1,5‐ a ]pyrimidines are well recognized [16–18] and are associated with [4,3‐ a ], [4,3‐ c ], [1,5‐ c ] systems [19–21] . A large number of TPs also exhibit antiviral, [22] anti‐Alzheimer's property, [23] and as CRFI receptor antagonist, [24] Further, they also exhibit antibacterial, [25] antioxidant, [26] antimalarial, [27] antifungal, [28] antidiabetic, [29] activity and as agrochemical agents [30] …”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10][11][12][13][14][15] The antitumor properties of 1,2,4-Triazolo[1,5-a]pyrimidines are well recognized [16][17][18] and are associated with [4,3-a], [4,3-c], [1,5-c] systems. [19][20][21] A large number of TPs also exhibit antiviral, [22] anti-Alzheimer's property, [23] and as CRFI receptor antagonist, [24] Further, they also exhibit antibacterial, [25] antioxidant, [26] antimalarial, [27] antifungal, [28] antidiabetic, [29] activity and as agrochemical agents. [30] Keeping in view the biological importance of TPs we synthesized a new class of thioalkylated (benzyl/phenacyl) 1,2,4-Triazolo [1,5-a]pyrimidine analogues under multicomponent approach(MCR) which is an effective and reliable green approach.…”

Section: Introductionmentioning

confidence: 99%

Efficient Four‐Component Synthesis of 1,2,4‐Triazolo[1,5‐a]pyrimidines and Their In Vitro Antiproliferative Studies

Venkatesham,

Kalonia,

Sangolkar

et al. 2023

ChemistrySelect

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Triazolopyrimidines are emerging as potential anticancer agents. Herein, we report a novel one‐pot four component synthesis of 2‐((2‐oxo‐2‐phenylethyl/benzyl)thio)‐10‐phenyl‐4,10‐dihydro‐9H‐indeno[1,2‐d][1,2,4]‐Triazolo[1,5‐a]pyrimidin‐9‐ones by the reaction of 1,3‐indanedione, aromatic aldehyde, 5‐amino‐4H‐1,2,4‐Triazol‐3‐thiol and phenacyl bromide in acetic acid with piperidine as catalyst at 90 °C for 13 hours. All the final compounds were identified on the basis of their FT‐IR, 1H NMR, 13C NMR and HRMS. The synthesized compounds were evaluated for their cell growth inhibition potential using MTT and wound healing assay, 13 compounds induced concentration dependent inhibition with IC50 below 10 μM against breast cancer cell lines (MCF‐7). Further, the molecular docking simulation were carried out for all the derivatives, amongst these thio phenacyl, 2,4‐dichlorophenyl 9H‐indeno [1,2,4]‐Triazolo[1,5‐a]pyrimidin‐9‐one (5 g) shows good binding interaction with amino acid residues. This is further confirmed by wound healing assay which shows that 5 g inhibits cell migration at increasing concentrations.

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“…Also, it was observed that sulfur linked 1,2,4-triazole compounds were relatively efficient antimicrobial agents without resistance (Turan-Zitouni et al, 2005;Shiradkar et al, 2007;Jalilian et al, 2000;Rostami, Manesh, Samie, 2013;Sun et al, 2014). In addition, a large number of synthesized 1,2,4-triazole derivatives were reported and associated with significant antioxidant activities (Bindu, Vijayalakshmi, Manikandan, 2020;Kaddouri Y et al, 2020;Dorovic et al, 2019;Koparir, 2019;Tumosienė et al, 2019;Tumosienė et al, 2018;Behalo, Amine, Fouda, 2017;Tumosienė et al, 2016) The thiazole systems, which are known to have an antimicrobial activity are also effective azole rings.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial and antioxidant activities of pyridyl substituted thiazolyl triazole derivatives

Tay

Duran

Kayağil

et al. 2022

Braz. J. Pharm. Sci.

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In this present study, 63 different 5-[4-methyl-2-(pyridin-3/4-yl)thiazole-5-yl]-4-substituted-3substituted benzylthio-4H-1,2,4-triazole derivatives were synthesized, and evaluated for their in vitro antimicrobial activity against various human pathogenic microorganisms and antioxidant activity. The derivatives were synthesized in a multi-step synthesis procedure including triazole and thiazole ring closure reactions, respectively. The synthesized derivatives (A1-24; B1-39) were screened for their antibacterial, antifungal, and antioxidant activities compared to standard agents. The derivatives possessing 3-pyridyl moiety particularly exhibited relatively high antibacterial activity (MIC= < 3.09-500 µg/mL) against Gram-positive bacteria, and compounds possessing 4-pyridyl moiety showed remarkable antioxidant activity.

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Synthesis and discovery of triazolo-pyridazine-6-yl-substituted piperazines as effective anti-diabetic drugs; evaluated over dipeptidyl peptidase-4 inhibition mechanism and insulinotropic activities

Cited by 17 publications

References 33 publications

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

Efficient Four‐Component Synthesis of 1,2,4‐Triazolo[1,5‐a]pyrimidines and Their In Vitro Antiproliferative Studies

Synthesis, antimicrobial and antioxidant activities of pyridyl substituted thiazolyl triazole derivatives

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