Design, synthesis, in silico and in vitro screening of 1,2,4-thiadiazole analogues as non-peptide inhibitors of beta-secretase

Gurjar, Archana S.; Andrisano, Vincenza; Simone, Angela De; Velingkar, Vinay

doi:10.1016/j.bioorg.2014.09.002

Cited by 36 publications

(20 citation statements)

References 25 publications

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“…Generally, the peaks at around 6.8–8.3 ppm were related to the protons on the pyridine and benzene rings . The peaks at 8.5 ppm and 8.7 ppm could be assigned to the protons on −NH on the urea groups . Furthermore, the 13 C NMR spectra of the synthesized products (BUCAIL, 2CBUCAIL, 3CBUCAIL, 4CBUCAIL, 3,4CBUCAIL, 2FBUCAIL, and 2BBUCAIL) exhibited peaks at 110–175 ppm (carbons of pyridine ring, benzene ring, and CO), also confirming the presence of urea groups.…”

Section: Resultsmentioning

confidence: 70%

Synthesis and Characterization of Inulin Derivatives Bearing Urea Groups with Promising Antifungal Activity

Zhang

Tan

et al. 2018

Starch Stärke

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The toxicity concerns associated with chemical fungicides currently on the market have resulted in an increased demand for alternative ecofriendly fungicides. As a biodegradable and biocompatible dietary fiber, inulin shows potential as such a compound, given its lack of toxicity. In the current study, seven novel inulin derivatives with promising antifungal activity (BUCAIL, 2CBUCAIL, 3CBUCAIL, 4CBUCAIL, 3,4CBUCAIL, 2FBUCAIL, and 2BBUCAIL) are synthesized via condensation reactions of chloroacetyl inulin (CAIL) with urea groups bearing 4‐amino‐pyridine. Their structures are confirmed using FT‐IR, 1H NMR, 13C NMR, and elemental analysis. Their antifungal activity against three kinds of phytopathogen (Fusarium oxysporum f. sp. niveum, Phomopsis asparagus, and Fusarium oxysporum f. sp. cucumebrium Owen) is evaluated using the mycelial growth rate in vitro at concentrations of 0.10, 0.25, 0.50, 0.75, and 1.0 mg mL−1. Results reveal that all seven inulin derivatives show improved antifungal properties compared with unmodified inulin, and two obvious inhibition rules are found: 3,4CBUCAIL > 4CBUCAIL > 3CBUCAIL > 2CBUCAIL > BUCAIL > CAIL > inulin and 2FBUCAIL > 2CBUCAIL > 2BBUCAIL > BUCAIL > CAIL > inulin. Thus, the introduction of urea groups into inulin derivatives could be key to increasing the antifungal activity of such compounds.

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Section: Resultsmentioning

confidence: 70%

Synthesis and Characterization of Inulin Derivatives Bearing Urea Groups with Promising Antifungal Activity

Zhang

Tan

et al. 2018

Starch Stärke

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“…Indeed, similar dehydrations of primary carboxamides using an acidic reagent such as POCl 3 , SOCl 2 are well documented in literature. 24,25 More recent, chemoselective and milder methods were also reported, where ethyl dichlorophosphate/DBU system or methyl (carboxysulfamoyl)triethylammonium hydroxide (Burgess reagent) were used as the dehydrating reagents. 26,27 In addition, Vilsmeier reagents, 28 bromodimethylsulfonium bromide (BDMS), 29 PdCl 2 in aqueous acetonitrile, 30 Swern oxidation conditions and other catalytic or alternative methods using silanes, silazanes, chlorosilanes, alkoxysilanes, and aminosilanes were also described.…”

Section: Resultsmentioning

confidence: 99%

Chlorocarbonylsulfenyl Chloride Cyclizations Towards Piperidin-3-yl-oxathiazol-2-ones as Potential Covalent Inhibitors of Threonine Proteases

Jukič¹,

Grabrijan²,

Kadić³

et al. 2017

ACSi

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Using rescaffolding approach, we designed piperidine compounds decorated with an electrophilic oxathiazol-2-one moiety that is known to confer selectivity towards threonine proteases. Our efforts to prepare products according to the published procedures were not successful. Furthermore we identified major side products containing nitrile functional group, resulting from carboxamide dehydration. We systematically optimized reaction conditions towards our desired products to identify heating of carboxamides with chlorocarbonylsulfenyl chloride and sodium carbonate as base in dioxane at 100 °C. Our efforts culminated in the preparation of a small series of piperidin-3-yl-oxathiazol-2-ones that are suitable for further biological evaluation.

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“…They have known to exhibit diverse biological activities such as in vitro inhibition of cyclooxygenase and 5-lipoxygenase activities 3 . New acylated 5-thio-beta-D-glucopyranosylimino-disusbstituted 1,3,4-thiadiazoles prepared by cycloaddition of the glycosyl isothiocyanate with the reactive intermediates 1-aza-2-azoniaallene hexachloro antimonates, and have been tested in vitro antiviral activity against HIV-1, HIV-2, human cytomegallovirus (HMCV) [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] .…”

Section: Introductionmentioning

confidence: 99%

“…Therapeutic importance of these rings prompted us to develop selective molecules in which substituent could be arranged in a pharmacophoric pattern to display higher pharmacological activities. Thiadiazoles have occupied an important place in drug industry, 1,3,4-thiadiazoles have wide applications in many fields 5 . 1,3,4-thiadiazole derivatives possess interesting biological activity probably conferred to them due to strong aromaticity of the ring system which leads to great in vivo stability and generally, a lack of toxicity for higher vertebrates, including humans when diverse functional group that interact with biological receptor are attached to aromatic ring 6 .…”

Section: Introductionmentioning

confidence: 99%

Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

Asif¹

2016

Mediterr.J.Chem.,

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Thiadiazoles are an important class of heterocyclic compounds that exhibit diverse applications in organic synthesis, pharmaceutical and biological applications. They are also useful as oxidation inhibitors, cyanine dyes, metal chelating agents, anti-corrosion agents. Researchers across the globe are working on this moiety due to their broad spectrum of applications of thiadiazole chemistry. This article provides information about developments, exploration, synthetic strategies, techniques for the synthesis of thiadiazoles and their diverse biological activities, structure-activity relationship of the compounds and physical properties. This article is an important tool for organic and medicinal chemists to develop newer thiadiazole compounds that could be better agents in terms of efficacy and safety.

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Design, synthesis, in silico and in vitro screening of 1,2,4-thiadiazole analogues as non-peptide inhibitors of beta-secretase

Cited by 36 publications

References 25 publications

Synthesis and Characterization of Inulin Derivatives Bearing Urea Groups with Promising Antifungal Activity

Synthesis and Characterization of Inulin Derivatives Bearing Urea Groups with Promising Antifungal Activity

Chlorocarbonylsulfenyl Chloride Cyclizations Towards Piperidin-3-yl-oxathiazol-2-ones as Potential Covalent Inhibitors of Threonine Proteases

Chemistry, synthesis and progress report on biological activities of thiadiazole compounds - a review

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