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

页码：146 / 156

页数：11

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