The trans–cis and the azide–tetrazole ring-chain isomerization of 2-azido-1,3-azoles: Quantum chemical study

Karakuş, Nihat; Demirel, Merdan

doi:10.1016/j.molstruc.2015.03.041

Cited by 19 publications

(2 citation statements)

References 37 publications

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“…Very small amounts of impurities other than the deprotected precursor (candesartan azide, 10 ) were observed, suggesting good stability of the tetrazole group during the click reaction. As reported previously, the stability of the tetrazole isomers depends on several factors, such as the nature of substituents, solvents, and temperature, which will determine the dominant form in the tetrazole/azide equilibrium. ,, Our results confirm that the azide group at the benzimidazole moiety of 7 was more prone to react than the less favored azide open form of the tetrazole ring under the click reaction conditions used in this study.…”

Section: Resultssupporting

confidence: 88%

Synthesis of the Novel AT₁ Receptor Tracer [¹⁸F]Fluoropyridine–Candesartan via Click Chemistry

et al. 2020

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A novel 7-((4-(3-((2-[ 18 F]fluoropyridin-3-yl)oxy)propyl)-1 H -1,2,3-triazol-1-yl)methyl)-1 H -benzo[ d ]imidazole derivative of the angiotensin II type-1 receptor (AT 1 R) blocker candesartan, [ 18 F]fluoropyridine–candesartan, was synthesized via the copper-catalyzed azide–alkyne cycloaddition click reaction between 2-[ 18 F]fluoro-3-(pent-4-yn-1-yloxy)pyridine ([ 18 F]FPyKYNE) and the tetrazole-protected azido-candesartan derivative, followed by acid deprotection. This three-step, two-pot, and two-step purification synthesis was done within 2 h. The use of tris[(1-hydroxypropyl-1 H -1,2,3-triazol-4-yl)methyl]amine (THPTA) as a Cu(I) stabilizing agent increased the overall radiochemical yield by 4-fold (10 ± 2%, n = 13) compared to the reaction without THPTA (2.4 ± 0.2%, n = 3; decay-corrected from 18 F produced at the end-of-beam). Complete separation of [ 18 F]FPyKYNE from its nitro precursor and [ 18 F]fluoropyridine–candesartan from the deprotected azido-candesartan allowed for high molar activities (>380 GBq/μmol) of the tracer. The use of 0.1% trifluoroacetic acid in water for reformulation and the addition of sodium ascorbate to the final formulation (1.6 ± 0.2 GBq/mL, n = 3) prevented tracer radiolysis with >97% radiochemical purity for a period of up to 10 h after the end-of-synthesis. A significant reduction in the uptake (86 ± 3%, n = 8) of the tracer was observed ex vivo in rats (at 20 min postinjection) in the AT 1 R-rich kidney cortex following pretreatment with saturating doses of the AT 1 R antagonist candesartan or losartan. This specific binding to AT 1 R was confirmed in vitro in the rat renal cortex (autoradiography) by a reduction of 26 ± 5% ( n = 12) with losartan coincubation (10 μM). These favorable binding properties support further studies to assess the potential of [ 18 F]fluoropyridine–candesartan as a tracer for the positron emission tomography imaging of renal AT 1 R.

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Section: Resultssupporting

confidence: 88%

Synthesis of the Novel AT₁ Receptor Tracer [¹⁸F]Fluoropyridine–Candesartan via Click Chemistry

et al. 2020

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“… [18] . Trans-cis isomerization was first investigated in photochromic compounds such as azobenzenes, azines, stilbenes, cinnamoyls, diarylethenes [19] , [20] , [21] . However, according to M. F. Budyka [22] and O. Kharchenko et al [23] , polymers containing styrylquinoline moieties can be a potential substitutes for azobenzenes, due to their ability to reversibly transform between their trans and cis form when exposed to light or thermal stimulation.…”

Section: Introductionmentioning

confidence: 99%

Impact of doping on the optoelectronic, electronic and nonlinear optical properties and on the reactivity of photochromic polymers containing styrylquinoline fragments: Hartree-Fock and DFT study

Noudem¹,

Fouejio²,

Mveme³

et al. 2022

Heliyon

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Electronic Properties of Artificial Metal‐DNA Base Pair Complexes Formed from Hydroxypyridone Base

Üngördü

Tezer

2020

ChemistrySelect

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The metal‐mediated hydroxypyridone base pairs containing Ni2+, Cu2+, Zn2+, Pd2+, Cd2+, Pt2+, and Hg2+ ions were designed theoretically using by density functional theory (DFT) method in Gaussian 09 program. The calculations which were performed in the gas phase, methanol, water, and formamide were done at B3LYP functional with LANL2DZ and 6–311++G (d, p) basis sets which were used metals and rest atoms, respectively. The Gibbs free energies of the complexes were calculated and their relative stabilities were determined in the mentioned fields. Furthermore, geometric parameters, HOMO, LUMO, energy gap energies of the compounds were computed in all media and effect on these parameters of solvents were determined. Based on these parameters, the relative conductivities of the investigated molecules were predicted. On the other hand, using Atomistix ToolKit (ATK‐VNL) 2016 program, nonequilibrium Green's function (NEGF) calculations based on the combination DFT of the mentioned complexes were carried out. The transport properties of the molecules were found in detailed via NEGF‐DFT method.

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The trans–cis and the azide–tetrazole ring-chain isomerization of 2-azido-1,3-azoles: Quantum chemical study

Cited by 19 publications

References 37 publications

Synthesis of the Novel AT₁ Receptor Tracer [¹⁸F]Fluoropyridine–Candesartan via Click Chemistry

Synthesis of the Novel AT₁ Receptor Tracer [¹⁸F]Fluoropyridine–Candesartan via Click Chemistry

Impact of doping on the optoelectronic, electronic and nonlinear optical properties and on the reactivity of photochromic polymers containing styrylquinoline fragments: Hartree-Fock and DFT study

Electronic Properties of Artificial Metal‐DNA Base Pair Complexes Formed from Hydroxypyridone Base

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The trans–cis and the azide–tetrazole ring-chain isomerization of 2-azido-1,3-azoles: Quantum chemical study

Cited by 19 publications

References 37 publications

Synthesis of the Novel AT1 Receptor Tracer [18F]Fluoropyridine–Candesartan via Click Chemistry

Synthesis of the Novel AT1 Receptor Tracer [18F]Fluoropyridine–Candesartan via Click Chemistry

Impact of doping on the optoelectronic, electronic and nonlinear optical properties and on the reactivity of photochromic polymers containing styrylquinoline fragments: Hartree-Fock and DFT study

Electronic Properties of Artificial Metal‐DNA Base Pair Complexes Formed from Hydroxypyridone Base

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Synthesis of the Novel AT₁ Receptor Tracer [¹⁸F]Fluoropyridine–Candesartan via Click Chemistry

Synthesis of the Novel AT₁ Receptor Tracer [¹⁸F]Fluoropyridine–Candesartan via Click Chemistry