Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)

Patrick J Hrdlicka; Nicolai K Andersen; Jan Stenvang; Flemming G Hansen; Kim F Haselmann; Claus Nielsen; Jesper Wengel

doi:10.1016/j.bmc.2005.01.029

Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)

Patrick J Hrdlicka, Nicolai K Andersen, Jan Stenvang, Flemming G Hansen, Kim F Haselmann, Claus Nielsen, Jesper Wengel

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

23 Citationer (Scopus)

Abstract

The synthesis of branched and conformationally restricted analogs of the anticancer nucleosides 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd) is presented. Molecular modeling and (1)H NMR coupling constant analysis revealed that the furanose rings of all analogs except the LNA analog are conformationally biased towards South conformation, and are thus mimicking the structure of ECyd. All target nucleosides were devoid of anti-HIV or anticancer activity.

Originalsprog	Engelsk
Tidsskrift	Bioorganic & Medicinal Chemistry
Vol/bind	13
Udgave nummer	7
Sider (fra-til)	2597-621
Antal sider	25
ISSN	0968-0896
DOI	https://doi.org/10.1016/j.bmc.2005.01.029
Status	Udgivet - 1 apr. 2005
Udgivet eksternt	Ja

Adgang til dokumentet

10.1016/j.bmc.2005.01.029

Citationsformater

Hrdlicka, P. J., Andersen, N. K., Stenvang, J., Hansen, F. G., Haselmann, K. F., Nielsen, C., & Wengel, J. (2005). Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd). Bioorganic & Medicinal Chemistry, 13(7), 2597-621. https://doi.org/10.1016/j.bmc.2005.01.029

Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd). / Hrdlicka, Patrick J; Andersen, Nicolai K; Stenvang, Jan et al.
I: Bioorganic & Medicinal Chemistry, Bind 13, Nr. 7, 01.04.2005, s. 2597-621.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

Hrdlicka, PJ, Andersen, NK, Stenvang, J, Hansen, FG, Haselmann, KF, Nielsen, C & Wengel, J 2005, 'Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)', Bioorganic & Medicinal Chemistry, bind 13, nr. 7, s. 2597-621. https://doi.org/10.1016/j.bmc.2005.01.029

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abstract = "The synthesis of branched and conformationally restricted analogs of the anticancer nucleosides 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd) is presented. Molecular modeling and (1)H NMR coupling constant analysis revealed that the furanose rings of all analogs except the LNA analog are conformationally biased towards South conformation, and are thus mimicking the structure of ECyd. All target nucleosides were devoid of anti-HIV or anticancer activity.",

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AU - Hrdlicka, Patrick J

AU - Andersen, Nicolai K

AU - Stenvang, Jan

AU - Hansen, Flemming G

AU - Haselmann, Kim F

AU - Nielsen, Claus

AU - Wengel, Jesper

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AB - The synthesis of branched and conformationally restricted analogs of the anticancer nucleosides 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd) is presented. Molecular modeling and (1)H NMR coupling constant analysis revealed that the furanose rings of all analogs except the LNA analog are conformationally biased towards South conformation, and are thus mimicking the structure of ECyd. All target nucleosides were devoid of anti-HIV or anticancer activity.

KW - Anti-HIV Agents

KW - Antineoplastic Agents

KW - Cell Line

KW - Cell Line, Tumor

KW - Cell Survival

KW - Crystallography, X-Ray

KW - Cytidine

KW - Humans

KW - Models, Molecular

KW - Molecular Mimicry

KW - Nucleic Acid Conformation

KW - Uridine

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DO - 10.1016/j.bmc.2005.01.029

M3 - Journal article

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SN - 0968-0896

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JO - Bioorganic & Medicinal Chemistry

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