Carbocyclodipeptides as modified nucleosides: synthesis and anti-HIV activities

被引：1

作者：

Chhikara, Bhupender S. ^{[1
]}

Rao, M. Sudershan ^{[2
]}

Rao, V. Kameshwara ^{[2
]}

Kumar, Anil ^{[2
]}

Buckheit, Karen W. ^{[3
]}

Buckheit, Robert W., Jr. ^{[3
]}

Parang, Keykavous ^{[1
,2
,4
]}

机构：

[1] Univ Rhode Isl, Dept Biomed & Pharmaceut Sci, Coll Pharm, Kingston, RI 02881 USA

[2] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India

[3] ImQuest BioSci Inc, Frederick, MD 21704 USA

[4] Chapman Univ, Sch Pharm, Irvine, CA 92618 USA

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2014年 / 92卷 / 12期

基金：

美国国家卫生研究院;

关键词：

anti-HIV; carbopeptides; cyclodipeptide; nucleoside analogues; 2 '-deoxyribofuranosyl; CELLULAR UPTAKE; ANALOGS; PRODRUGS; CYCLODIPEPTIDES; DERIVATIVES; INHIBITION;

D O I：

10.1139/cjc-2014-0356

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new class of nucleoside analogues were synthesized using cyclic dipeptides and modified 2'-deoxyfuranoribose sugars to introduce flexibility by peptides in place of common nucleoside bases and to determine their biological properties. The synthesis was carried out by coupling of a protected ribose sugar with synthesized dipeptides in the presence of hexamethyldisilazane and trimethylsilyltriflate. The final products were characterized by NMR and high-resolution MS-TOF spectroscopy. The compounds were evaluated for anti-HIV activities. 1-(4-Azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,6-diisopropylpiperazine2,5-dione (compound 14) containing 3- and 6-isopropyl groups in the base and 3'-azide (EC50 = 1.96 mu mol/L) was the most potent compound among all of the synthesized analogs.

引用

页码：1145 / 1149

页数：5

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