Synthesis, photochemistry and computational study of novel 1,2,3-triazole heterostilbenes: Expressed biological activity of their electrocyclization photoproducts

Mlakić, Milena; Faraho, Ivan; Odak, Ilijana; Talić, Stanislava; Vukovinski, Ana; Raspudić, Anamarija; Bosnar, Martina; Zadravec, Rahela; Ratković, Ana; Lasić, Kornelija; Marinić, Željko; Barić, Danijela; Škorić, Irena

doi:10.1016/j.bioorg.2022.105701

Cited by 14 publications

(12 citation statements)

References 40 publications

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“…In this way, several functionalities of these new resveratrol–maltol hybrids, as well as resveratrol–thiophene hybrids with previously improved antioxidative activity, were examined as a necessary approach to finding more effective drugs for complicated neurodegenerative diseases. As shown in our previous studies, sulfur analogs were found to be active in cholinesterase inhibition [ 33 , 34 ] and antioxidant activity [ 26 ]; therefore, some diheterostilbenes (maltol-heteroaromatic resveratrol analogs) are prepared in this work too (structures D and E , Figure 2 ).…”

Section: Introductionmentioning

confidence: 94%

Resveratrol–Maltol and Resveratrol–Thiophene Hybrids as Cholinesterase Inhibitors and Antioxidants: Synthesis, Biometal Chelating Capability and Crystal Structure

et al. 2022

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New resveratrol–thiophene and resveratrol–maltol hybrids were synthesized as cholinesterase inhibitors and antioxidants. As with photostability experiments, biological tests also found remarkable differences in the properties and behavior of thiophene and maltol hybrids. While resveratrol–thiophene hybrids have excellent inhibitory and antioxidant properties (similar to the activity of reference drug galantamine), maltols have been proven to be weaker inhibitors and antioxidants. The molecular docking of selected active ligands gave insight into the structures of docked enzymes. It enabled the identification of interactions between the ligand and the active site of both cholinesterases. The maltols that proved to be active cholinesterase inhibitors were able to coordinate Fe3+ ion, forming complexes of 1:1 composition. Their formation constants, determined by spectrophotometry, are very similar, lgK = 11.6–12.6, suggesting that Fe3+ binds to the common hydroxy-pyranone moiety and is hardly affected by the other aromatic part of the ligand. Accordingly, the characteristic bands in their individual absorption spectra are uniformly red-shifted relative to those of the free ligands. The crystal structures of two new resveratrol–maltol hybrids were recorded, giving additional information on the molecules’ intermolecular hydrogen bonds and packing. In this way, several functionalities of these new resveratrol hybrids were examined as a necessary approach to finding more effective drugs for complicated neurodegenerative diseases.

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Section: Introductionmentioning

confidence: 94%

Resveratrol–Maltol and Resveratrol–Thiophene Hybrids as Cholinesterase Inhibitors and Antioxidants: Synthesis, Biometal Chelating Capability and Crystal Structure

et al. 2022

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Section: Introductionmentioning

confidence: 99%

“…According to our previous experience in the field of the synthesis and photochemistry of heterostilbene molecules [27][28][29], we herein designed, synthesized, and photochemically transformed the new amino-thienostilbenes (Figure 1I) as interesting structures with potential biological activity and specific chemical and photophysical characteristics. The basic structure of new and known heterostilbenes and their photocyclization products: new amino-thienostilbenes (I), amino-oxazolostilbenes (II) [27], naphthooxazolo-amines (III) [27], and thienobenzo-triazoles (IV) [29], as proven active compounds, and amino-styryl organic dye (V) [30].…”

Section: Introductionmentioning

confidence: 99%

“…An additional motivation for the design of new heterostilbenes and their photocyclization products was provided by the results of biological testing of 1,2,3-triazolo(thieno)stilbenes and their photoproducts thienobenzo/naphtho-triazoles, which showed BChE inhibition associated with the inhibition of TNFα cytokine Figure 1. The basic structure of new and known heterostilbenes and their photocyclization products: new amino-thienostilbenes (I), amino-oxazolostilbenes (II) [27], naphthooxazolo-amines (III) [27], and thienobenzo-triazoles (IV) [29], as proven active compounds, and amino-styryl organic dye (V) [30].…”

Section: Introductionmentioning

confidence: 99%

“…New amino-thienostilbenes, stable under acidic conditions and with favorable photophysical properties, could be used to prepare their water-soluble ammonium salts as potentially biologically active compounds. On the other hand, their functionalized photocyclization products could be good candidates for cholinesterase inhibition, given that they have the same basic skeleton as some already proven bioactive derivatives [28,29]. New styryl-thiophene benzylamines 2-8 (Scheme 1) are synthesized by the Buchwald-Hartwig amination reactions [27] from the previously prepared chloro derivative 1 [34].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Photochemistry, Computational Study and Potential Application of New Styryl-Thiophene and Naphtho-Thiophene Benzylamines

Mlakić

Odak

Faraho

et al. 2022

IJMS

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In this research, the synthesis, photochemistry, and computational study of new cis- and trans-isomers of amino-thienostilbenes is performed to test the efficiency of their production and acid resistance, and to investigate their electronic structure, photoreactivity, photophysical characteristics, and potential biological activity. The electronic structure and conformations of synthesized thienostilbene amines and their photocyclization products are examined computationally, along with molecular modeling of amines possessing two thiophene rings that showed inhibitory potential toward cholinesterases. New amino-styryl thiophenes, with favorable photophysical properties and proven acid resistance, represent model compounds for their water-soluble ammonium salts as potential styryl optical dyes. The comparison with organic dyes possessing a trans-aminostilbene subunit as the scaffold shows that the newly synthesized trans-aminostilbenes have very similar absorbance wavelengths. Furthermore, their functionalized cis-isomers and photocyclization products are good candidates for cholinesterase inhibitors because of the structural similarity of the molecular skeleton to some already proven bioactive derivatives.

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Synthesis, characterization, in vitro antimycobacterial and cytotoxicity evaluation, DFT calculations, molecular docking and ADME studies of new isomeric benzimidazole-1,2,3-triazole-quinoline hybrid mixtures

Nyoni,

Ncube,

Kubheka

et al. 2023

Bioorganic Chemistry

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Synthesis, photochemistry and computational study of novel 1,2,3-triazole heterostilbenes: Expressed biological activity of their electrocyclization photoproducts

Cited by 14 publications

References 40 publications

Resveratrol–Maltol and Resveratrol–Thiophene Hybrids as Cholinesterase Inhibitors and Antioxidants: Synthesis, Biometal Chelating Capability and Crystal Structure

Resveratrol–Maltol and Resveratrol–Thiophene Hybrids as Cholinesterase Inhibitors and Antioxidants: Synthesis, Biometal Chelating Capability and Crystal Structure

Synthesis, Photochemistry, Computational Study and Potential Application of New Styryl-Thiophene and Naphtho-Thiophene Benzylamines

Synthesis, characterization, in vitro antimycobacterial and cytotoxicity evaluation, DFT calculations, molecular docking and ADME studies of new isomeric benzimidazole-1,2,3-triazole-quinoline hybrid mixtures

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