Synthesis, mechanism elucidation and biological insights of tellurium(IV)-containing heterocycles

Piovan, Leandro, Souza, João Pedro A., Bandeira, Pamela T., Menezes, Leociley R. A., Bespalhok, Mateus B., Scariot, Débora B., Garcia, Francielle P., Giese, Siddhartha O. K., Hughes, David L., Nakamura, Celso V., Barison, Andersson, Oliveira, Alfredo R. M. and Campos, Renan B. (2021) Synthesis, mechanism elucidation and biological insights of tellurium(IV)-containing heterocycles. Chemistry – A European Journal, 27 (58). pp. 14427-14437. ISSN 0947-6539

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Inspired by the synthetic and biological potential of organotellurium substances, a series of five- and six-membered ring organotelluranes containing a Te−O bond were synthesized and characterized. Theoretical calculations elucidated the mechanism for the oxidation-cyclization processes involved in the formation of the heterocycles, consistent with chlorine transfer to hydroxy telluride, followed by a cyclization step with simultaneous formation of the new Te−O bond and deprotonation of the OH group. Moreover, theoretical calculations also indicated anti-diastereoisomers to be major products for two chirality center–containing compounds. Antileishmanial assays against Leishmania amazonensis promastigotes disclosed 1,2λ 4-oxatellurane LQ50 (IC 50=4.1±1.0; SI=12), 1,2λ 4-oxatellurolane LQ04 (IC 50=7.0±1.3; SI=7) and 1,2λ 4-benzoxatellurole LQ56 (IC 50=5.7±0.3; SI=6) as more powerful and more selective compounds than the reference, being up to four times more active. A stability study supported by 125Te NMR analyses showed that these heterocycles do not suffer structural modifications in aqueous-organic media or at temperatures up to 65 °C.

Item Type: Article
Additional Information: Funding Information: The authors thank the National Council for Scientific and Technological Development (CNPq, Brazil), and the Coordination for the Improvement of Higher Level Personnel (CAPES, Brazil) for financial support and fellowships of J.P.A.S., P.T.B., L.R.A.M., M.B.B., D.B.S., F.P.G., D.L.H. and S.O.K.G..
Uncontrolled Keywords: te nmr spectroscopy,hypervalency,leishmania,oxidation–cyclization mechanism,tellurium,catalysis,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1500/1503
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: LivePure Connector
Date Deposited: 25 Aug 2021 09:54
Last Modified: 23 Oct 2022 02:56
DOI: 10.1002/chem.202102287

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