5-SUBSTITUTED PYRIMIDINE L-2′-DEOXYRIBONUCLEOSIDES: SYNTHETIC, QUANTUM CHEMICAL, AND NMR STUDIES

被引：7
作者：
Amer, Adel [1 ]
Senior, Samir [1 ,2 ]
Fan, Xuesen [3 ]
机构：
[1] Univ Alexandria, Fac Sci, Dept Chem, Alexandria, Egypt
[2] King Abdulaziz Univ, Rabigh Coll Sci & Art, Dept Chem, Jeddah, Saudi Arabia
[3] Henan Normal Univ, Sch Chem & Environm Sci, Henan Key Lab Environm Pollut Control, Xinxiang 453007, Henan, Peoples R China
来源：
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2012年 / 31卷 / 1-3期
关键词：
L-nucleoside; tautomerism; NMR; DFT calculations; ANTI-ORTHOPOXVIRUS ACTIVITY; IN-VITRO; NUCLEOSIDE; ENERGIES; MODEL;
D O I：
10.1080/15257770.2011.641651
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
As a part of an ongoing medicinal chemistry, we report here the synthesis and structure evaluation of 1-(2-deoxy-3,5-di-O-acetylpentofuranosyl)-5-[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-4H-pyrazol-4-ylidene) pyrimidine-2,4(1H,3H)-dione 5 and 5-[bis(3-methyl-5-oxo-1-phenyl-4,5-dihydro-4H-pyrazol-4-yl)methyl-1-(2-deoxy-3,5-di-O-acetylpentofuranosyl)pyrimidine-2,4(1H,3H)-dione 6 derived from 3',5'-di-O-acetyl-5-formyl-2'-deoxy-beta-L-uridine 1. Base hydrolysis of compounds 1 and 6 furnished their deacetylated analogues in good yields, whereas hydrolysis of 5 was troublesome. Structural features of these molecules are discussed by NMR spectra analyses and density functional theory quantum chemical calculations. The newly synthesized L-analogues show no significant activity against vaccinia and cowpox viruses.
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页码：42 / 54
页数：13
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