Regioselectively <i>N</i>‐Functionalised 14‐Membered Azapyridinomacrocycles Bearing Trialkanoic Acid Side Chains as Ligands for Lanthanide Ions

Dioury, Fabienne; Sylvestre, Isabelle; Siaugue, Jean‐Michel; Wintgens, Véronique; Ferroud, Clotilde; Favre‐Réguillon, Alain; Foos, J.; Guy, Alain

doi:10.1002/ejoc.200400264

Cited by 20 publications

(14 citation statements)

References 39 publications

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“…Large differences in polarity of the resulting di-, tri-, and tetra-substituted azamacrocycles facilitated chromatographic isolation of trisubstituted cyclens (42a,b) and cyclams (43a,b) (Scheme 12). [3] The interaction of cyclam (32) with a large excess of iodoacetamide (44) in acetone in the presence of i-Pr 2 NEt as a base is not following the usual pattern: only pure triamide (45) as powders almost insoluble in water and acetone is obtained. Afterwards, it is transferred to triacid (46).…”

Section: Functionalisation Of Macrocycles With Preservation Of Their mentioning

confidence: 99%

Functionalisation of Macroheterocycles with Preserving and Changing Their Sizes

Ishmuratov¹,

Yakovleva²,

Выдрина³

et al. 2017

MHC

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Section: Functionalisation Of Macrocycles With Preservation Of Their mentioning

confidence: 99%

Functionalisation of Macroheterocycles with Preserving and Changing Their Sizes

Ishmuratov¹,

Yakovleva²,

Выдрина³

et al. 2017

MHC

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“…Similar synthetic strategies have also been used for preparation of related macrocyclic ligands with higher number of ring amine groups, higher number of carbon atoms connecting ring amine groups, or more than one pyridine ring in the macrocycle [358][359][360][361][362][363].…”

Section: H 3 Pcta and Related Ligandsmentioning

confidence: 99%

Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

Kotek¹,

Kubíček²,

Hermann³

et al. 2013

The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging

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“…Synthesis of 4b, 5b, and 6b has been previously reported in 100, 81, and 100% yield, resp. [41]. 6-(Bromomethyl)pyridine-2-methanol (9).…”

Section: Experimental Partmentioning

confidence: 99%

Polyazacyclophanes Incorporating Two Pyridine Units and a Heteroaromatic Pendant Group as Potential Cleaving Agents of mRNA 5′-cap Structure

Zhang

Mikkola

Lönnberg

2005

C&B

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Four hexaazacyclophanes, 16a-d, incorporating two pyridine units and a (pyridin-2-yl)methyl or (quinolin-2-yl)methyl pendant group at one of the ring N-atoms have been prepared. The key step of the synthesis is an intermolecular cyclization of N,N-bis{[6-(tosyloxymethyl)pyridin-2-yl]methyl}-2-nitrobenzenesulfonamide (7) with either tert-butyl bis{2-[(2-nitrophenylsulfonyl)amino]ethyl}carbamate (2a) or tert-butyl bis{3-[(2-nitrophenylsulfonyl)amino]propyl}carbamate (2b) in the presence of anhydrous Cs(2)CO(3). Removal of the acid-labile tert-butoxycarbonyl protection then allows attachment of the pendant group by reductive alkylation to the exposed secondary amino group, and deprotection of the remaining aliphatic ring N-atoms completes the synthesis. The ability of the cyclophanes and their dinuclear Cu(2+) and Zn(2+) complexes to cleave the mRNA cap structure, m(7)G(5')pppG(5') (1), has been studied.

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Regioselectively N‐Functionalised 14‐Membered Azapyridinomacrocycles Bearing Trialkanoic Acid Side Chains as Ligands for Lanthanide Ions

Cited by 20 publications

References 39 publications

Functionalisation of Macroheterocycles with Preserving and Changing Their Sizes

Functionalisation of Macroheterocycles with Preserving and Changing Their Sizes

Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

Polyazacyclophanes Incorporating Two Pyridine Units and a Heteroaromatic Pendant Group as Potential Cleaving Agents of mRNA 5′-cap Structure

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