Synthesis of monoazacrown ethers under phase-transfer catalysis

Luk’yanenko, N. G.; Basok, S. S.; Kulygina, E. Yu.; Bogashchenko, Tatiana Yu.; Yakovenko, Irene S.

doi:10.1134/s1070428012100156

Cited by 10 publications

(12 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Also under development are 21-crown-7 receptors, though we do not present results from those here. Synthesis of 15-crown-5 ether (15c5) and 18-crown-6 ether (18c6) binding domains is achieved in parallel, via ether synthesis under phase transfer conditions [17] with N-benzylbisethanolamine acting as the linchpin that reacts at two ends of various length polyethers. Hydrogenolysis of the N-benzyl protecting group yields unmodified aza-crown ethers ready for the installation of various fluorophores.…”

Section: Preliminary Results With Custom-made Aza-crown Derivativesmentioning

confidence: 99%

Progress toward Barium Tagging in High Pressure Xenon Gas with Single Molecule Fluorescence Imaging

Byrnes¹,

Foss²,

Jones³

et al. 2019

J. Phys.: Conf. Ser.

View full text Add to dashboard Cite

We present an update on the development of techniques to adapt Single Molecule Fluorescent Imaging for the tagging of individual barium ions in high pressure xenon gas detectors, with the goal of realizing a background-free neutrinoless double beta decay technology. Previously reported progress is reviewed, including the recent demonstration of single barium dication sensitivity using SMFI. We then describe two important advances: 1) the development of a new class of custom barium sensing fluorescent dyes, which exhibit a significantly stronger response to barium than commercial calcium sensing compounds in aqueous solution; 2) the first demonstration of a dry-phase chemosensor for barium ions. This proceeding documents work presented at the 9th Symposium on Large TPCs for Rare Event Detection in Paris, France.

show abstract

Section: Preliminary Results With Custom-made Aza-crown Derivativesmentioning

confidence: 99%

Progress toward Barium Tagging in High Pressure Xenon Gas with Single Molecule Fluorescence Imaging

Byrnes¹,

Foss²,

Jones³

et al. 2019

J. Phys.: Conf. Ser.

View full text Add to dashboard Cite

show abstract

“…All aza-crowns used for their substitution were commercially available, except 1-aza-21-crown-7. Its synthesis has been published [17,18,20]; however, the reaction of pentaethylene glycol bistosylate and N-benzyl diol either with NaH as a base [20] or in the presence of CsCl, tetrabutylammonium bromide and 50% aqueous NaOH as a base [18] failed. Finally, 1-aza-21-crown-7 (5, see Scheme 1) was successfully prepared using potassium tertbutoxide as a base for an overall yield of 47% (after deprotection), similarly as published by Maeda et al [17] In our work, the direct addition of potassium tert-butoxide instead of its in situ formation and different purification procedure were applied.…”

Section: Synthesismentioning

confidence: 97%

“…Removal of the benzyl protection group was performed according to the published procedure [18] with some alterations mentioned below. A mixture of 10% Pd/C (40 mg) in MeOH (3 mL) was saturated with hydrogen and stirred for 1 h at rt.…”

Section: -Aza-21-crown-7 (5)mentioning

confidence: 99%

“…Finally, 1-aza-21-crown-7 (5, see Scheme 1) was successfully prepared using potassium tertbutoxide as a base for an overall yield of 47% (after deprotection), similarly as published by Maeda et al [17] In our work, the direct addition of potassium tert-butoxide instead of its in situ formation and different purification procedure were applied. The benzyl protecting group was then removed by Pd/C catalyzed hydrogenation according to published procedure [18].…”

Section: Synthesismentioning

confidence: 99%

See 1 more Smart Citation

The role of the size of aza-crown recognition moiety in azaphthalocyanine fluorescence sensors for alkali and alkaline earth metal cations

et al. 2015

View full text Add to dashboard Cite

“…The starting aza-crown ethers (aza-15-crown-5, aza-18-crown-6, benzoaza-15-crown-5, 4,10-diaza-12-crown-4, 4,10-diaza-15-crown-5, 4,10-diaza-18-crown-6) [49][50][51], 6-(Bocamino)hexanoic and 4-(Boc-aminomethyl)benzoic acids, adamantane-1-carbonyl chloride, 2-(adamantan-1-yl)acetyl chloride, and diborane [52,53] were obtained by standard methods. Their spectral characteristics and physical constants were identical to those given in the literature.…”

Section: General Informationmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Modeling of Aza-Crown Ethers

Basok¹,

Schepetkin

Khlebnikov

et al. 2021

Molecules

View full text Add to dashboard Cite

Synthetic and natural ionophores have been developed to catalyze ion transport and have been shown to exhibit a variety of biological effects. We synthesized 24 aza- and diaza-crown ethers containing adamantyl, adamantylalkyl, aminomethylbenzoyl, and ε-aminocaproyl substituents and analyzed their biological effects in vitro. Ten of the compounds (8, 10–17, and 21) increased intracellular calcium ([Ca2+]i) in human neutrophils, with the most potent being compound 15 (N,N’-bis[2-(1-adamantyl)acetyl]-4,10-diaza-15-crown-5), suggesting that these compounds could alter normal neutrophil [Ca2+]i flux. Indeed, a number of these compounds (i.e., 8, 10–17, and 21) inhibited [Ca2+]i flux in human neutrophils activated by N-formyl peptide (fMLF). Some of these compounds also inhibited chemotactic peptide-induced [Ca2+]i flux in HL60 cells transfected with N-formyl peptide receptor 1 or 2 (FPR1 or FPR2). In addition, several of the active compounds inhibited neutrophil reactive oxygen species production induced by phorbol 12-myristate 13-acetate (PMA) and neutrophil chemotaxis toward fMLF, as both of these processes are highly dependent on regulated [Ca2+]i flux. Quantum chemical calculations were performed on five structure-related diaza-crown ethers and their complexes with Ca2+, Na+, and K+ to obtain a set of molecular electronic properties and to correlate these properties with biological activity. According to density-functional theory (DFT) modeling, Ca2+ ions were more effectively bound by these compounds versus Na+ and K+. The DFT-optimized structures of the ligand-Ca2+ complexes and quantitative structure–activity relationship (QSAR) analysis showed that the carbonyl oxygen atoms of the N,N’-diacylated diaza-crown ethers participated in cation binding and could play an important role in Ca2+ transfer. Thus, our modeling experiments provide a molecular basis to explain at least part of the ionophore mechanism of biological action of aza-crown ethers.

show abstract

Synthesis of monoazacrown ethers under phase-transfer catalysis

Cited by 10 publications

References 15 publications

Progress toward Barium Tagging in High Pressure Xenon Gas with Single Molecule Fluorescence Imaging

Progress toward Barium Tagging in High Pressure Xenon Gas with Single Molecule Fluorescence Imaging

The role of the size of aza-crown recognition moiety in azaphthalocyanine fluorescence sensors for alkali and alkaline earth metal cations

Synthesis, Biological Evaluation, and Molecular Modeling of Aza-Crown Ethers

Contact Info

Product

Resources

About