Total synthesis of CRM646-A and -B, two fungal glucuronides with potent heparinase inhibition activities

被引：43

作者：

Wang, P ^{[1
]}

Zhang, ZJ ^{[1
]}

Yu, B ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 22期

关键词：

D O I：

10.1021/jo051384k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinolp-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approach involved construction of the phenol glucuronidic linkage, via coupling of the orsellinate derivative 27 with glucuronate bromide 7, before assembly of the phenolic ester linkage in the depside aglycone. Attempts via direct glycosylation of the depside aglycone derivatives were not successful.

引用

页码：8884 / 8889

页数：6

共 42 条

[1] Versatile use of ytterbium(III) triflate and acid washed molecular sieves in the activation of glycosyl trifluoroacetimidate donors.: Assemblage of a biologically relevant tetrasaccharide sequence of Globo H
Adinolfi, M
Iadonisi, A
Ravidà, A
Schiattarella, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) : 5316 - 5319
[2] Ahn J. S., 2001, Chemical Abstracts, V2001, P75833, Patent No. [2001046385, WO2001046385]
[3] Heparanases: endoglycosidases that degrade heparan sulfate proteoglycans
Bame, KJ
[J]. GLYCOBIOLOGY, 2001, 11 (06) : 91R - 98R
[4] GLYCOSYLATED DERIVATIVES OF BENZOPHENONE, BENZHYDROL, AND BENZHYDRIL AS POTENTIAL VENOUS ANTITHROMBOTIC AGENTS
BELLAMY, F
HORTON, D
MILLET, J
PICART, F
SAMRETH, S
CHAZAN, JB
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (07) : 898 - 903
[5] THE SYNTHESIS OF ARYL-D-GLUCOPYRANOSIDURONIC ACIDS
BOLLENBACK, GN
LONG, JW
BENJAMIN, DG
LINDQUIST, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (12) : 3310 - 3315
[6] BRUCE I, 1992, J CHEM RES-S, P224
[7] Efficient sialylation with phenyltrifluoroacetimidates as leaving groups
Cai, ST
Yu, B
[J]. ORGANIC LETTERS, 2003, 5 (21) : 3827 - 3830
[8] SYNTHESIS OF THE D-GLUCURONIC ACID CONJUGATES OF N-(4-HYDROXYPHENYL)RETINAMIDES AND N-(2-HYDROXYETHYL)-RETINAMIDES
DAWSON, MI
HOBBS, PD
[J]. CARBOHYDRATE RESEARCH, 1980, 85 (01) : 121 - 129
[9] Heparanase, a potential regulator of cell-matrix interactions
Dempsey, LA
Brunn, GJ
Platt, JL
[J]. TRENDS IN BIOCHEMICAL SCIENCES, 2000, 25 (08) : 349 - 351
[10] Total synthesis of quercetin 3-sophorotrioside
Du, YG
Wei, GH
Linhardt, RJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) : 2206 - 2209

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