Synthesis of D-Glucosamine-Modified Benzo[d][1,2]selenazol-3-(2H)-one Derivatives

被引：4

作者：

Zhang, Zhongwei ^{[1
]}

Ren, Sumei ^{[1
]}

Wan, Shengbiao ^{[1
]}

Li, Wei ^{[1
]}

Jiang, Tao ^{[1
]}

机构：

[1] Ocean Univ China, Minist Educ, Key Lab Marine Drugs, Sch Med & Pharm, Qingdao 266003, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 23期

关键词：

Benzoisoselenazolone; organoselenium-saccharide derivatives; reaction mechanism; SELENIUM; CHLORIDE;

D O I：

10.1080/00397910903434562

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new class of organoselenium-saccharide derivatives, 2-amino-2-deoxy--D-glucose-modified benzo[d][1,2]selenazol-3-(2H)-one derivatives, has been synthesized via the cyclization reaction of 2-(chloroseleno)benzoyl chloride and O-protected D-glucosamine derivatives. An efficient synthetic method for the preparation of this type of compounds was developed. It has been found that acetone can react with the chloroseleno group under basic conditions, and organoselenium-saccharide derivatives with free hydroxy groups were obtained only when the OH-1 group of the saccharide was protected.

引用

页码：3438 / 3446

页数：9

共 22 条

[1] THE USE OF N-ALKOXYCARBONYL DERIVATIVES OF 2-AMINO-2-DEOXY-D-GLUCOSE AS DONORS IN GLYCOSYLATION REACTIONS [J].

BOULLANGER, P ;

JOUINEAU, M ;

BOUAMMALI, B ;

LAFONT, D ;

DESCOTES, G .

CARBOHYDRATE RESEARCH, 1990, 202 :151-164

[2]

DALLACKER F, 1991, CHEM ZTG, V115, P135

[3] Synthesis, structure, and antiproliferative activity of selenophenfurin, an inosine 5'-monophosphate dehydrogenase inhibitor analogue of selenazofurin [J].

Franchetti, P ;

Cappellacci, L ;

AbuSheikha, G ;

Jayaram, HN ;

Gurudutt, VV ;

Sint, T ;

Schneider, BP ;

Jones, WD ;

Goldstein, BM ;

Perra, G ;

DeMontis, A ;

Loi, AG ;

LaColla, P ;

Grifantini, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (11) :1731-1737

[4]

JIANG T, 2007, Patent No. 101016319

[5] BROAD-SPECTRUM ANTIVIRAL ACTIVITY OF 2-BETA-D-RIBOFURANOSYLSELENAZOLE-4-CARBOXAMIDE, A NEW ANTIVIRAL AGENT [J].

KIRSI, JJ ;

NORTH, JA ;

MCKERNAN, PA ;

MURRAY, BK ;

CANONICO, PG ;

HUGGINS, JW ;

SRIVASTAVA, PC ;

ROBINS, RK .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1983, 24 (03) :353-361

[6] Selenenylation-acylation of ketones with 2-chloroselenobenzoyl chloride.: A novel route to benzo[b]selenophenes [J].

Kloc, K ;

Mlochowski, J .

TETRAHEDRON LETTERS, 2001, 42 (29) :4899-4902

[7] Differently glycosidated 2-amino-2-deoxy-D-glucopyranosiduronic acids as building blocks in peptide synthesis [J].

Kyas, A ;

Feigel, M .

HELVETICA CHIMICA ACTA, 2005, 88 (09) :2375-2396

[8] Chemistry of biologically important synthetic organoselenium compounds [J].

Mugesh, G ;

du Mont, WW ;

Sies, H .

CHEMICAL REVIEWS, 2001, 101 (07) :2125-2179

[9] The reactions of 2-(chloroseleno)benzoyl chloride with nucleophiles [J].

Osajda, M ;

Mlochowski, J .

TETRAHEDRON, 2002, 58 (37) :7531-7537

[10]

Paulmier C., 1986, SELENIUM REAGENTS IN

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