Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)
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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, Nicolai K; Stenvang, Jan; Hansen, Flemming G; Haselmann, Kim F; Nielsen, Claus; Wengel, Jesper.
In: Bioorganic & Medicinal Chemistry, Vol. 13, No. 7, 01.04.2005, p. 2597-621.Research output: Contribution to journal › Journal article › Research › peer-review
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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, Nicolai K
AU - Stenvang, Jan
AU - Hansen, Flemming G
AU - Haselmann, Kim F
AU - Nielsen, Claus
AU - Wengel, Jesper
PY - 2005/4/1
Y1 - 2005/4/1
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 (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.
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
U2 - 10.1016/j.bmc.2005.01.029
DO - 10.1016/j.bmc.2005.01.029
M3 - Journal article
C2 - 15755661
VL - 13
SP - 2597
EP - 2621
JO - Bioorganic & Medicinal Chemistry
JF - Bioorganic & Medicinal Chemistry
SN - 0968-0896
IS - 7
ER -
ID: 59323511