Synthesis and growth inhibitory properties of glucosamine-derived glycerolipids

被引：56

作者：

Yang, GL

Franck, RW

Bittman, R

Samadder, P

Arthur, G

机构：

[1] CUNY Hunter Coll, Dept Chem, New York, NY 10021 USA

[2] CUNY Queens Coll, Flushing, NY 11367 USA

[3] Univ Manitoba, Dept Biochem & Med Genet, Winnipeg, MB R3E 0W3, Canada

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 02期

关键词：

D O I：

10.1021/ol006783a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 2-Amino C-glycerolipid Ib was synthesized by using the Ramberg-Backlund rearrangement as the key step. beta -C-Glycerolipid Ib exhibits in vitro antiproliferative effects strikingly similar to those of O-glycoside analogue 1a.

引用

页码：197 / 200

页数：4

共 46 条

[11] Synthesis and evaluation of the antiproliferative effects of 1-O-hexadecyl-2-O-methyl-3-O-(2'-acetamido-2'-deoxy-beta-D-glucopyranosyl)-sn-glycerol and 1-O-hexadecyl-2-O-methyl-3-O-(2'-amino-2'-deoxy-beta-D-glucopyranosyl)-sn-glycerol an epithelial cancer cell growth [J].

Erukulla, RK ;

Zhou, X ;

Samadder, P ;

Arthur, G ;

Bittman, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (07) :1545-1548

[12] Escherichia coli β-galactosidase recognizes a high-energy conformation of C-lactose, a nonhydrolizable substrate analogue.: NMR and modeling studies of the molecular complex [J].

Espinosa, JF ;

Montero, E ;

Vian, A ;

García, JL ;

Dietrich, H ;

Schmidt, RR ;

Martín-Lomas, M ;

Imberty, A ;

Cañada, FJ ;

Jiménez-Barbero, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (06) :1309-1318

[13] Experimental evidence of conformational differences between C-glycosides and O-glycosides in solution and in the protein-bound state: The C-lactose/O-lactose case [J].

Espinosa, JF ;

Canada, FJ ;

Asensio, JL ;

MartinPastor, M ;

Dietrich, H ;

MartinLomas, M ;

Schmidt, RR ;

JimenezBarbero, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) :10862-10871

[14]

FALCONER RA, 2000, 20 INT CARB S HAMB A

[15] A concise synthesis of C-glycosyl phosphate and phosphonate analogues of N-acetyl-α-D-glucosamine 1-phosphate [J].

Gaurat, O ;

Xie, J ;

Valéry, JM .

TETRAHEDRON LETTERS, 2000, 41 (08) :1187-1189

[16]

Griffin FK, 1999, ANGEW CHEM INT EDIT, V38, P2939, DOI 10.1002/(SICI)1521-3773(19991004)38:19<2939::AID-ANIE2939>3.0.CO

[17]

2-S

[18] A Ramberg-Backlund approach to exo-glycals [J].

Griffin, FK ;

Murphy, PV ;

Paterson, DE ;

Taylor, RJK .

TETRAHEDRON LETTERS, 1998, 39 (44) :8179-8182

[19] SYNTHETICALLY USEFUL EXTRUSION REACTIONS OF ORGANIC SULFUR, SELENIUM AND TELLURIUM COMPOUNDS [J].

GUZIEC, FS ;

SANFILIPPO, LJ .

TETRAHEDRON, 1988, 44 (20) :6241-6285

[20] THIOSUGARS .1. SYNTHESIS OF DERIVATIVES OF 2-AMINO-2-DEOXY-1-THIO-D-GLUCOSE [J].

HORTON, D ;

WOLFROM, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (05) :1794-&

← 1 2 3 4 5 →