Efficient ‘one-pot’ methodology for the synthesis of novel tetrahydro-β-carboline, tetrahydroisoquinoline and tetrahydrothienopyridine derivatives

Ionescu, Alexandra; Cornut, Damien; Soriano, Sébastien; Guissart, Céline; Antwerpen, Pierre Van; Jabin, Ivan

doi:10.1016/j.tetlet.2013.08.135

Cited by 9 publications

(3 citation statements)

References 17 publications

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“…In this work, all reagents were purchase from commercial suppliers and used without further purification. 3-Thienylethanmine was prepared following a reported literature procedure . Synthesis of dimethyl 3,3′-((2-(thiophen-3-yl)ethyl)azanediyl)dipropionate and poly(3,3′-((2-(thiophen-3-yl)ethyl)azanediyl)dipropionic acid) was conducted following a reported literature procedure .…”

Section: Methodsmentioning

confidence: 99%

“…3-Thienylethanmine was prepared following a reported literature procedure. 48 Synthesis of dimethyl 3,3′-((2-(thiophen-3-yl)ethyl)azanediyl)dipropionate and poly(3,3′-((2-(thiophen-3-yl)ethyl)azanediyl)dipropionic acid) was conducted following a reported literature procedure. 43 The viologen cross-linker was synthesized following preparatory procedures from our previous work.…”

Section: Methodsmentioning

confidence: 99%

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Photoinduced Electron Transfer and Changes in Surface Free Energy in Polythiophene-Polyviologen Bilayered Thin Films

et al. 2021

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Bipyridiniums, also known as viologens, are well-documented electron acceptors that are generally easy to synthesize on a large scale and reversibly cycle between three oxidation states (V2+, V•+, and V0). Accordingly, they have been explored in a number of applications that capitalize on their dynamic redox chemistry, such as redox-flow batteries and electrochromic devices. Viologens are also particularly useful in photoinduced electron transfer (PET) processes and therefore are of interest in photovoltaic applications that typically rely on electron-rich donors like polythiophene (PTh). However, the PET mechanism and relaxation dynamics between interfacing PTh and viologen-based thin films has not been well studied as a function of thickness of the acceptor layer. Here, a novel, bilayered thin film composite was fabricated by first spin-coating PTh onto glass slides, followed by spin-coating and curing polyviologen (PV)-based micron-sized films of variable thicknesses (0.5–11.3 μm) on top of the PTh layer. The electron-transfer mechanism and relaxation dynamics from the PTh sublayer into the upper PV film were investigated using femtosecond transient absorption (fTA) spectroscopy and electrochemistry to better understand how the charge-transfer/relaxation lifetimes could be extended using thicker PV acceptor films. The fTA experiments were performed under inert N2 conditions as well as in ambient O2. The latter shortened the lifetimes of the electrons in the PV layer, presumably due to O2 triplet-based trap sites. Contact angle measurements using H2O and MeI were also performed on top of the bilayered films to measure changes in surface free energy that would aid the assessment related to efficiency of the combined processes involving light penetration, photoexcitation, electron mobility, and relaxation from within the bilayered thin films. Insights gained from this work will support the development of future devices that employ viologen-based materials as an alternative electron-acceptor that is both easily processable and scalable.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Photoinduced Electron Transfer and Changes in Surface Free Energy in Polythiophene-Polyviologen Bilayered Thin Films

et al. 2021

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“…The thieno [2,3-b]pyridine system and its derivatives hold great importance in medicinal chemistry and drug discovery. They have been shown to exhibit a wide range of pharmacological properties, including anti-rheumatoid arthritis [1], anti-inflammatory [2], antiviral [3], antioxidant [4], antiplatelet [5], antithrombotic [1], antitumor [6], and an timicrobial activities [1,7]. This makes them valuable candidates for the development of new therapeutic agents.…”

Section: Introductionmentioning

confidence: 99%

Exploring the Chemical Reactivity, Molecular Docking, Molecular Dynamic Simulation and ADMET Properties of a Tetrahydrothienopyridine Derivative Using Computational Methods

et al. 2023

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This study investigates the crystal structure, physicochemical properties, and pharmacokinetic profile of Ethyl 2-amino-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate (EAMT) as a potential therapeutic agent. The crystal structure was analyzed using Hirshfeld surface analysis in conjunction with the quantum theory of atoms in molecules (QT-AIM). Non-covalent interactions were evaluated through reduced-density gradient reduction, revealing that the EAMT crystal is stabilized by hydrogen bonds between EAMT molecules in the crystal and between EAMT molecules and water molecules. The molecular electrostatic nature of interactions was examined using MESP, while global and local descriptors were calculated to assess the compound’s reactivity. Molecular docking with the Adenosine A1 receptor was performed and validated through a 50 ns molecular dynamics simulation (MDS). Results suggest that EAMT influences protein structure, potentially stabilizing specific secondary structure elements. The compactness analysis showed a slightly more compact protein conformation and a marginally increased solvent exposure in the presence of the EAMT ligand, as indicated by Rg and SASA values. The total binding free energy (ΔG total) was determined to be −114.56 kcal/mol. ADMET predictions demonstrated EAMT’s compliance with Lipinski’s and Pfizer’s rule of five, indicating good oral availability. The compound may exhibit low-potency endocrine activity. In conclusion, EAMT presents potential as a therapeutic candidate, warranting further exploration of its molecular interactions, pharmacokinetics, and potential safety concerns.

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ChemInform Abstract: Efficient ′One‐Pot′ Methodology for the Synthesis of Novel Tetrahydro‐β‐carboline, Tetrahydroisoquinoline and Tetrahydrothienopyridine Derivatives.

et al. 2014

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Efficient 'One-Pot' Methodology for the Synthesis of Novel Tetrahydro-β-carboline, Tetrahydroisoquinoline and Tetrahydrothienopyridine Derivatives. -This simple and general method gives an efficient access to the title compounds via the Pictet-Spengler type cyclization. The obtained products are useful precursors for the synthesis of compounds with potential antitumoral activity. -(IONESCU, A.; CORNUT, D.; SORIANO, S.; GUISSART, C.; VAN ANTWERPEN, P.; JABIN*, I.; Tetrahedron Lett. 54 (2013) 45, 6087-6089, http://dx.doi.org/10.1016/j.tetlet.2013.08.135 ; Lab. Chim. Org., Univ. Libre Bruxelles, B-1050 Bruxelles, Belg.; Eng.) -Mais 11-175

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Efficient ‘one-pot’ methodology for the synthesis of novel tetrahydro-β-carboline, tetrahydroisoquinoline and tetrahydrothienopyridine derivatives

Cited by 9 publications

References 17 publications

Photoinduced Electron Transfer and Changes in Surface Free Energy in Polythiophene-Polyviologen Bilayered Thin Films

Photoinduced Electron Transfer and Changes in Surface Free Energy in Polythiophene-Polyviologen Bilayered Thin Films

Exploring the Chemical Reactivity, Molecular Docking, Molecular Dynamic Simulation and ADMET Properties of a Tetrahydrothienopyridine Derivative Using Computational Methods

ChemInform Abstract: Efficient ′One‐Pot′ Methodology for the Synthesis of Novel Tetrahydro‐β‐carboline, Tetrahydroisoquinoline and Tetrahydrothienopyridine Derivatives.

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