A novel series of tetrahydrothieno[2,3-<i>c</i>]pyridin-2-yl derivatives: fluorescence spectroscopy and BSA binding, ADMET properties, molecular docking, and DFT studies

Serdaroğlu, Goncagül; Uludag, Nesimi; Üstün, Elvan; Çolak, Naki

doi:10.1039/d3nj01648j

Cited by 5 publications

(1 citation statement)

References 111 publications

(144 reference statements)

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“…The title compound coded as ST was synthesized according to the relevant literature studies [21][22][23] from 1,4-dioxaspiro [4.5]decan-8-one (0.01 mmol), malononitrile, sulfur (0.01 mmol), and morpholine (0.01 mmol), and used for the synthesis of the chloro benzamide-thiophene compounds (Scheme 1).…”

Section: -Amino-47-dihydro-5h-spiro[benzo[b]thiophene-62'-[13]dioxola...mentioning

confidence: 99%

Synthesis, Structural Analysis, Antimicrobial Activity and The Molecular Electrostatic Potential Surface (MEP) of 2/3/4-Chloro Benzamide-Spiro[Benzo[B]Thiophene-Dioxolane] Derivatives

Çolak,

Şahin,

Erten

et al. 2024

Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi

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In this research, 2-amino-4,7-dihydro-5H-spiro[benzo[b]thiophene-6,2'-[1,3]dioxolane]-3-carbonitrile (ST) was synthesized using the Gewald method, starting with 1,4-dioxaspiro[4,5]decan-8-one ketone. The structures of compounds were characterized through FT-IR, 1H-NMR, and 13C-NMR spectra. The antimicrobial properties of the compounds were examined by the disk diffusion process. The compounds (N1-3) did not exhibit effectiveness against the E. Coli (ATCC) and S. Aureus (ATCC) bacteria. The molecular electrostatic potential surface (MEP) of all compounds was calculated via DFT calculations based on the optimized geometries at the B3LYP/6-31G (d,p) level of theory. Negative potential regions were located over the oxygen and nitrogen atoms, whereas positive potential regions were identified over the oxygen and sulfur atoms. Conceptually, computations of the molecular structures of the compounds were carried out using molecular modeling software, specifically GaussView 5.0 and the GAUSSIAN 09 package programs. Additionally, computations were performed for the HOMO and LUMO molecular orbitals of isolated molecules in the gas phase. Molecular electrostatic potential (MEP) surfaces were used to visualize potential interactions between receptors and ligands over the steady-state geometries of the molecules and to highlight the electrophilic and nucleophilic regions of the molecules.

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Section: -Amino-47-dihydro-5h-spiro[benzo[b]thiophene-62'-[13]dioxola...mentioning

confidence: 99%

Synthesis, Structural Analysis, Antimicrobial Activity and The Molecular Electrostatic Potential Surface (MEP) of 2/3/4-Chloro Benzamide-Spiro[Benzo[B]Thiophene-Dioxolane] Derivatives

Çolak,

Şahin,

Erten

et al. 2024

Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi

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Advancing Pyrrole Synthesis through DDQ Catalysis: A Comprehensive Research Incorporating DFT, ADMT, and Molecular Docking Analysis

Serdaroğlu,

Uludağ,

Üstün

2024

ChemistrySelect

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The construction of pyrroles is an important heterocyclic group comprising many compounds with interesting properties that have led to numerous applications in various fields. We delineate a new synthetic method for the rapid construction of tree‐substituted pyrroles from readily available ketoximes as starting materials and also a new mechanism and method has been proposed. It is presented that substituted pyrroles were efficiently synthesized in high yields (up to 81 % yield) through the cyclization reaction of starting ketoximes mediated by 2,3‐dichlor‐5,6‐dicyanobenzoquinone (DDQ). Utilizing this protocol various pyrrole derivatives were synthesized from diethyl acetylene dicarboxylate (DEAD). We then developed the dehydrogenation reaction mechanism of this formation, also studied in detail, also all synthesized compounds were analyzed in detail by spectroscopic techniques (FT‐IR, 1H NMR, 13CNMR) which were compared with the computational data estimated at B3LYP/6‐311G** level. The thermochemical and electronic properties of the pyrroles were evaluated after optimizing and then confirming the equilibrium structures. ADMT scores were also considered to estimate/elucidate the possible bioavailability tendencies as well as the toxicity. In addition, the interactions of the optimized molecules were evaluated by molecular docking methods against BSA “Bovine Serum Albumin” and LIF “Leukemia Inhibitory Factor”. The results obtained from this study will ideally provide a fundamental source in contemporary drug design in terms of both the key electronic properties underlying the possible reactivity features and toxicity.

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Green Synthesis of Pyrrole Derivatives Catalyzed by Molecular Sieves: DFT, ADMT, and Molecular Docking Investigations

Serdaroğlu,

Uludağ,

Üstün

2024

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A new synthetic methodology for the preparation by a different alternative method of five aryl pyrrole derivatives is produced from the corresponding ketoximes, giving diverse five‐membered N‐heterocycles in satisfactory yields. For the first time in literature, the synthetic catalyst molecular sieves were described. The simplicity and high response yield of this procedure are its standout qualities. Additionally, spectroscopic techniques (FT‐IR, 1H NMR, 13C NMR, elemental analysis) were used to confirm the structures of all synthesized compounds. FT‐IR and NMR computations with B3LYP/6‐311G** level by utilizing the G09 W package were performed to compare with observed data and evaluate the structural confirmation of novel pyrrole derivatives. Then, the lipophilic characterization and water solubility were computed to enlighten the physicochemical attitude. The ADMT properties were calculated to elucidate the possible bioavailability tendencies of the compounds and the adverse behaviour in terms of both medicinal and environmental. FMO analyses were also conducted to indicate/show the reactivity tendencies and possible regions. The molecular docking analyses of the optimized molecules were performed against Bovine Serum Albumin and Leukemia Inhibitory Factor. In conclusion, this study underscores the crucial role of green chemistry principles in developing novel synthetic methodologies, using environmentally benign catalysts like zeolite 3 Å.

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A novel series of tetrahydrothieno[2,3-c]pyridin-2-yl derivatives: fluorescence spectroscopy and BSA binding, ADMET properties, molecular docking, and DFT studies

Cited by 5 publications

References 111 publications

Synthesis, Structural Analysis, Antimicrobial Activity and The Molecular Electrostatic Potential Surface (MEP) of 2/3/4-Chloro Benzamide-Spiro[Benzo[B]Thiophene-Dioxolane] Derivatives

Synthesis, Structural Analysis, Antimicrobial Activity and The Molecular Electrostatic Potential Surface (MEP) of 2/3/4-Chloro Benzamide-Spiro[Benzo[B]Thiophene-Dioxolane] Derivatives

Advancing Pyrrole Synthesis through DDQ Catalysis: A Comprehensive Research Incorporating DFT, ADMT, and Molecular Docking Analysis

Green Synthesis of Pyrrole Derivatives Catalyzed by Molecular Sieves: DFT, ADMT, and Molecular Docking Investigations

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