Controlled synthesis and alkaline earth ion binding of switchable formamidoxime-based crown ether analogs

Yan, Yi; Zhao, Weiwen; Bhagavathy, Ganga Viswanathan; Faurie, Alexandre; Mosey, Nicholas J.; Petitjean, Anne

doi:10.1039/c2cc33090c

Cited by 9 publications

(6 citation statements)

References 31 publications

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“…Every independent molecule contains two symmetrical N-ethyl(pyridine-2-carboxiamide) moieties linked by a phenylamino bridge. It is noteworthy that the C═O bonds are oriented trans to the pyridine nitrogen atom, which are in accord with those reported for previous structures (Munro et al, 2010;Yan et al, 2012) [symmetry code: (iv) x+1/2, -y+1/2, z+1/2; (v) x-1/2, -y+1/2, z-1/2] (Table 1).…”

Section: Data Collectionsupporting

confidence: 90%

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N,N′-[2,2′-(Phenylazanediyl)bis(ethane-2,1-diyl)]dipicolinamide

Li¹,

Niu²,

Huang³

et al. 2013

Acta Cryst E

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The asymmetric unit of the title compound, C22H23N5O2, contains two independent molecules with similar conformations; the terminal pyridine rings are oriented at dihedral angles of 23.99 (8) and 18.07 (8)° with respect to the central benzene ring in one molecule and 28.99 (8) and 23.22 (8)° in the other. In the crystal, N—H⋯O and weak C—H⋯O hydrogen bonds link the molecules into a three-dimensional supramolecular structure. Weak intermolecular C—H⋯π interactions are also observed in the crystal.

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Section: Data Collectionsupporting

confidence: 90%

“…For the synthesis, see: Jain et al (2004); Lee et al (2006); Barnes et al (1978). For related structures, see: Adolph et al (2012); Munro & Wilson (2010); Yan et al (2012). Cu K radiation = 0.70 mm À1 T = 100 K 0.12 Â 0.08 Â 0.07 mm…”

Section: Related Literaturementioning

confidence: 99%

N,N′-[2,2′-(Phenylazanediyl)bis(ethane-2,1-diyl)]dipicolinamide

Li¹,

Niu²,

Huang³

et al. 2013

Acta Cryst E

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“…Small model systems with intramolecular and/or intermolecular hydrogen bonded amide groups are often employed to study these interactions in solution and in the solid state [ 4 ]. Aminobenzamides, for example, are commonly used as hydrogen-bond donors to form intramolecular hydrogen bonds with other O - or N -groups as hydrogen-bond acceptors [ 5 , 6 ]. The amides also work as dual hydrogen-bond donors and acceptors to form intramolecular hydrogen bonds between the adjacent amide-amide groups to construct linear sheets and helical conformations [ 7 , 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic, DFT, and XRD Studies of Hydrogen Bonds in N-Unsubstituted 2-Aminobenzamides

et al. 2017

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The structures of the mono- and the dihalogenated N-unsubstituted 2-aminobenzamides were characterized by means of the spectroscopic (1H-NMR, UV-Vis, FT-IR, and FT-Raman) and X-ray crystallographic techniques complemented with a density functional theory (DFT) method. The hindered rotation of the C(O)–NH2 single bond resulted in non-equivalence of the amide protons and therefore two distinct resonances of different chemical shift values in the 1H-NMR spectra of these compounds were observed. 2-Amino-5-bromobenzamide (ABB) as a model confirmed the presence of strong intramolecular hydrogen bonds between oxygen and the amine hydrogen. However, intramolecular hydrogen bonding between the carbonyl oxygen and the amine protons was not observed in the solution phase due to a rapid exchange of these two protons with the solvent and fast rotation of the Ar–NH2 single bond. XRD also revealed the ability of the amide unit of these compounds to function as a hydrogen bond donor and acceptor simultaneously to form strong intermolecular hydrogen bonding between oxygen of one molecule and the NH moiety of the amine or amide group of the other molecule and between the amine nitrogen and the amide hydrogen of different molecules. DFT calculations using the B3LYP/6-311++G(d,p) basis set revealed that the conformer (A) with oxygen and 2-amine on the same side predominates possibly due to the formation of a six-membered intramolecular ring, which is assisted by hydrogen bonding as observed in the single crystal XRD structure.

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“…2 Conjugation by opening of the anhydride could form two isomers but NMR studies showed only a single isomer to be formed. L 37 has been conjugated to trastuzumab at 25 1C and radiolabelled with 111 In for tumour targeted SPECT imaging. 3 A strain promoted catalyst free click reaction has been tested for peptide conjugation reaction of chelators for radioisotope complexation to avoid the problems of copper catalyst contamination.…”

Section: Targeted Radiopharmaceuticalsmentioning

confidence: 99%

“…A chelator combining amide and oxime groups L 68 selectively complexes alkaline earth ions such as calcium(II) with a pH dependence linked to protonation and cavity H-bonding motifs. 111…”

Section: Mixed Donor Macrocyclesmentioning

confidence: 99%

Macrocyclic coordination chemistry

Burke

Archibald

2013

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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This chapter reviews the literature published on macrocyclic coordination chemistry during 2012. The aim is to describe the key advances, focusing on complexes formed with transition metal and lanthanide ions. Porphyrin ligands and supramolecular chemistry are not covered. New chelator design, coordination complex formation and characterisation are presented along with details on the most common applications including luminescent compound formation, MRI contrast agents and radiopharmaceuticals. HighlightsIn 2012, some elegant studies and new tools for radiopharmaceutical imaging were reported. Cooper and co-workers carried out a comparative study of bifunctional chelators for 64 Cu giving a definitive answer to which had the most favourable properties for in vivo imaging use. 1 This is extremely important when chemists are creating tools for use by biologists and medics. Denat and co-workers reported a new bifunctional chelator; a glutaric acid anhydride derivative of DOTA that will have high impact as a tool for labelling proteins and peptides. 2,3 Caravan and co-workers advanced MRI contrast agent technology by developing an amino acid derivative of DOTA that allows high rigidity and improved high field relaxivity properties when incorporated into a peptide. 4 These optimised tools will allow molecular imaging applications to reach their full potential.Catalysis is also an important area for macrocyclic chelator and metal complex design with the role of the zirconium(IV) cyclam complex in polylactide formation particularly interesting. 5 A key advance was made in the work of Williams and Kember, where they generated a highly active catalyst for copolymerisation of epoxides and carbon dioxide, offering a non-toxic and cost effective alternative to current processes. 6

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Controlled synthesis and alkaline earth ion binding of switchable formamidoxime-based crown ether analogs

Abstract: The partial positive charge of amide protons is used to promote macrocyclization and form crown-ether analogs. Their deprotonation generates very selective pH-switchable alkaline earth ion receptors only in the presence of an appropriate substrate.

Cited by 9 publications

References 31 publications

N,N′-[2,2′-(Phenylazanediyl)bis(ethane-2,1-diyl)]dipicolinamide

N,N′-[2,2′-(Phenylazanediyl)bis(ethane-2,1-diyl)]dipicolinamide

Spectroscopic, DFT, and XRD Studies of Hydrogen Bonds in N-Unsubstituted 2-Aminobenzamides

Macrocyclic coordination chemistry

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