Synthesis and anti-HIV activity of guanidinoglycosides

被引：98

作者：

Baker, TJ ^{[1
]}

Luedtke, NW ^{[1
]}

Tor, Y ^{[1
]}

Goodman, M ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 26期

关键词：

D O I：

10.1021/jo001142e

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The new guanidinylation reagent N,N'-diBoc-N " -triflylguanidine was used to efficiently convert multiamine-containing glycosides including kanamycin A and B, tobramycin, paromomycin, and neomycin B to the corresponding fully guanidinylated analogues (guanidinoglycosides). This transformation occurs in the presence of H2O under mild conditions. Guanidinotobramycin and guanidinoneomycin B were found to, inhibit the replication of the HIV virus with activities approximately 100 times greater than the parent aminoglycosides.

引用

页码：9054 / 9058

页数：5

共 16 条

[1]

GUANIDINE ANALOGS OF A DEOXYSUGAR [J].

CHAN, AWY ;

GANEM, B .

TETRAHEDRON LETTERS, 1995, 36 (06) :811-814

[2]

Phosphotyrosine binding by ammonium- and guanidinium-modified cyclodextrins [J].

Cotner, ES ;

Smith, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1737-1739

[3]

AMINOGLYCOSIDE ANTIBIOTICS .7. DIHYDROSTREPTOMYCIN ANALOGS [J].

DELAWARE, DL ;

SHARMA, MS ;

IYENGAR, BS ;

REMERS, WA ;

PURSIANO, TA .

JOURNAL OF ANTIBIOTICS, 1986, 39 (02) :251-258

[4]

Diprotected triflylguanidines: A new class of guanidinylation reagents [J].

Feichtinger, K ;

Zapf, C ;

Sings, HL ;

Goodman, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :3804-3805

[5]

GravierPelletier C, 1996, SYNLETT, P275

[6]

Synthesis of a capped dicationic derivative of β-cyclodextrin [J].

Hauser, SL ;

Cotner, ES ;

Smith, PJ .

TETRAHEDRON LETTERS, 1999, 40 (15) :2865-2866

[7]

Guanidinoglycosides: A novel family of RNA ligands [J].

Luedtke, NW ;

Baker, TJ ;

Goodman, M ;

Tor, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) :12035-12036

[8]

The HIV-1 Rev protein [J].

Pollard, VW ;

Malim, MH .

ANNUAL REVIEW OF MICROBIOLOGY, 1998, 52 :491-532

[9]

RAKHIT S, 1995, Patent No. 9529926

[10]

CARBOHYDRATE BIGUANIDES AS POTENTIAL HYPOGLYCEMIC AGENTS [J].

REITZ, AB ;

TUMAN, RW ;

MARCHIONE, CS ;

JORDAN, AD ;

BOWDEN, CR ;

MARYANOFF, BE .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (09) :2110-2116

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