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 S Jepsen; Flemming G Hansen; Kim F Haselmann; Claus Nielsen; Jesper Wengel; Jan Stenvang

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 S Jepsen, Flemming G Hansen, Kim F Haselmann, Claus Nielsen, Jesper Wengel, Jan Stenvang

21 Citations (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.

Original language	English
Journal	Bioorganic & Medicinal Chemistry
Volume	13
Issue number	7
Pages (from-to)	2597-621
Number of pages	25
ISSN	0968-0896
DOIs	https://doi.org/10.1016/j.bmc.2005.01.029
Publication status	Published - 1 Apr 2005

Keywords

Anti-HIV Agents
Antineoplastic Agents
Cell Line
Cell Line, Tumor
Cell Survival
Crystallography, X-Ray
Cytidine
Humans
Models, Molecular
Molecular Mimicry
Nucleic Acid Conformation
Uridine

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmc.2005.01.029

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Hrdlicka, P. J., Andersen, N. K., Jepsen, J. S., Hansen, F. G., Haselmann, K. F., Nielsen, C., Wengel, J., & Stenvang, 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; Jepsen, Jan S et al.
In: Bioorganic & Medicinal Chemistry, Vol. 13, No. 7, 01.04.2005, p. 2597-621.

Research output: Contribution to journal › Journal article › Research › peer-review

Hrdlicka, PJ, Andersen, NK, Jepsen, JS, Hansen, FG, Haselmann, KF, Nielsen, C, Wengel, J & Stenvang, 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, vol. 13, no. 7, pp. 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 - Jepsen, Jan S

AU - Hansen, Flemming G

AU - Haselmann, Kim F

AU - Nielsen, Claus

AU - Wengel, Jesper

AU - Stenvang, Jan

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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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VL - 13

SP - 2597

EP - 2621

JO - Bioorganic & Medicinal Chemistry

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ER -

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

Abstract

Keywords

UN SDGs

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