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Synthesis 2020; 52(07): 1087-1095
DOI: 10.1055/s-0039-1691540
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© Georg Thieme Verlag Stuttgart · New York

Synthetic Approaches to the Bifunctional Chelators for Radio­nuclides Based On Pyridine-Containing Azacrown Compounds

Anastasia D. Zubenko  ∗
a   A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, 119991 Moscow, Russian Federation   Email: nastya.mutasova@yandex.ru
,
Anna A. Shchukina
a   A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, 119991 Moscow, Russian Federation   Email: nastya.mutasova@yandex.ru
b   D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya Sq. 9, 125047 Moscow, Russian Federation
,
Olga A. Fedorova
a   A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, 119991 Moscow, Russian Federation   Email: nastya.mutasova@yandex.ru
b   D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya Sq. 9, 125047 Moscow, Russian Federation
› Author AffiliationsThe work was supported by Russian Science Foundation (grant No 16-13-10226). The characterization of the products was performed with the financial support from the Ministry of Science and Higher Education of the Russian Federation using the equipment of Center for molecular composition studies of INEOS RAS.
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Publication History

Received: 11 October 2019

Accepted after revision: 03 December 2019

Publication Date:
16 December 2019 (online)

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Abstract

Synthetic ways to introduce functional groups (CO2Me, CO2H, OCH2CO2H, OCH2C≡CH, CH2OH, CH2Cl, CH2N3) into the pyridine ring of pyridine-containing azacrown compounds are described. These groups were introduced at position-4 of the pyridine ring, while keeping the macrocyclic carboxylate groups available for metal chelation. The derivatives were obtained by macrocyclization reaction of 4-substituted, trimethyl pyridine-2,4,6-tricarboxylate or by modification of methyl ester group in pyridine fragment of macrocycles. Obtained derivatives can be applied for preparing radiotherapeutic agents by conjugation to different vector biomolecules for targeted drug delivery to cancer cells without damaging healthy tissue.

Key words

bifunctional chelators - azacrown compounds - macro­cyclization - radiopharmaceuticals - bioconjugation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691540.
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