New acyclic quinoxaline nucleosides. Synthesis and anti-HIV activity

被引：23
|
作者：
Ali, Ibrahim A. I. [2 ]
Al-Masoudi, Iman A. [3 ]
Aziz, Nazik M. [4 ]
Al-Masoudi, Najim A. [1 ,4 ]
机构：
[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany
[2] Suez Canal Univ, Fac Sci, Dept Chem, Ismailia, Egypt
[3] Univ Basrah, Coll Vet Med, Basrah, Iraq
[4] Univ Sulaimania, Coll Sci, Dept Chem, Sulaimania, Iraq
来源：
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2008年 / 27卷 / 02期
关键词：
acyclonucleosides; alkylation; antiviral activity; glycosides; quinoxalines;
D O I：
10.1080/15257770701795920
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：
A series of acyclonucleosides substituted 1-(4,5-dihydroxypentyl) (13-8) and 2-(4,5-dihydroxypentyloxy)quinoxalines (19-24) were synthesized by the sharpless asymmetric dihydroxylation of the derivatives 1-6 and 7-12, respectively. Treatment of the quinoxaline base 26 with (R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl-p-toluenesulfonate (27) in the presence of NaH/DMF furnished 28. Acid hydrolysis of 28 gave 1-(2,3-dihydroxypropyl)-6,7-dimethyl-quinoxaline-2-one (29). Alternatively, 29 was prepared by sharpless dihydroxylation of 30. All the compounds were evaluated for their in vitro anti-HIV-1 and HIV-2 in MT-4 cell and found inactive, except 29, which showed inhibition of HIV-1 with EC50 value of 0.15 +/- 0.1 mu g/ml and a therapeutic index (SI) of 73.
引用
收藏
页码：146 / 156
页数：11
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