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, N.K. Andersen, J.S. Jepsen, F.G. Hansen, Kim Haselmann, C. Nielsen, Jesper Wengel

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

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 1H 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.

OriginalsprogEngelsk
TidsskriftBioorganic & Medicinal Chemistry
Vol/bind13
Udgave nummer7
Sider (fra-til)2597-2621
ISSN0968-0896
DOI
StatusUdgivet - 2005

Fingeraftryk

Nucleosides
Molecular modeling
Conformations
Nuclear magnetic resonance
HIV
1-(3-C-ethynylribopentofuranosyl)uracil
Proton Magnetic Resonance Spectroscopy

Citer dette

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title = "Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)",
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 1H 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.",
author = "Hrdlicka, {Patrick J.} and N.K. Andersen and J.S. Jepsen and F.G. Hansen and Kim Haselmann and C. Nielsen and Jesper Wengel",
year = "2005",
doi = "10.1016/j.bmc.2005.01.029",
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volume = "13",
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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, N.K.; Jepsen, J.S.; Hansen, F.G.; Haselmann, Kim; Nielsen, C.; Wengel, Jesper.

I: Bioorganic & Medicinal Chemistry, Bind 13, Nr. 7, 2005, s. 2597-2621.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)

AU - Hrdlicka, Patrick J.

AU - Andersen, N.K.

AU - Jepsen, J.S.

AU - Hansen, F.G.

AU - Haselmann, Kim

AU - Nielsen, C.

AU - Wengel, Jesper

PY - 2005

Y1 - 2005

N2 - 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 1H 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.

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 1H 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.

U2 - 10.1016/j.bmc.2005.01.029

DO - 10.1016/j.bmc.2005.01.029

M3 - Journal article

VL - 13

SP - 2597

EP - 2621

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

SN - 0968-0896

IS - 7

ER -