A SYNTHETIC APPROACH TO AROMATIC AMINOGLYCOSIDE AS A NEAMINE MIMIC

被引：0

作者：

Inoue, Ryo ^{[1
,2
]}

Matsuda, Sho ^{[1
]}

Oda, Yoshiki ^{[1
]}

Ooyama, Hirofumi ^{[1
]}

Yoshida, Akihiro ^{[1
]}

Hamasaki, Keita ^{[2
]}

Yamanoi, Takashi ^{[1
]}

机构：

[1] Noguchi Inst, Itabashi Ku, Tokyo 1730003, Japan

[2] Shibaura Inst Technol, Dept Appl Chem, Koto Ku, Tokyo 1358548, Japan

来源：

HETEROCYCLES | 2012年 / 84卷 / 02期

关键词：

Neamine Mimic; Aminoglycoside; Aromatic Glycoside; Glycosylation; Antibiotic; SMALL MOLECULES; RNA; MIMETICS; ANTIBIOTICS; DERIVATIVES; NEOMYCIN; ANALOGS; DESIGN; CORE; SITE;

D O I：

10.3987/COM-11-S(P)69

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes the synthetic approach to an aromatic alpha-glycoside as a mimic of neamine, which is a common core structure of some aminoglycoside antibiotics. We achieved the synthesis of the protected precursor of the neamine mimic, 4-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyloxy)-1,3-phenylenediamine, from N-acetyl-D-glucosamine and 2,4-diaminophenol as the starting materials using a glycosylation technique.

引用

页码：1335 / 1343

页数：9

共 24 条

[1] Metal catalyzed diazo transfer for the synthesis of azides from amines [J].

Alper, PB ;

Hung, SC ;

Wong, CH .

TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032

[2] Rational design of azepane-glycoside antibiotics targeting the bacterial ribosome [J].

Barluenga, S ;

Simonsen, KB ;

Littlefield, ES ;

Ayida, BK ;

Vourloumis, D ;

Winters, GC ;

Takahashi, M ;

Shandrick, S ;

Zhao, Q ;

Han, Q ;

Hermann, T .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (03) :713-718

[3] Synthesis of aminodisaccharide-nucleoside conjugates for RNA binding [J].

Cai, Li ;

Li, Qin ;

Ren, Bo ;

Yang, Zhen-Jun ;

Zhang, Liang-Ren ;

Zhang, Li-He .

TETRAHEDRON, 2007, 63 (34) :8135-8144

[4] Facile and regioselective preparation of partly O-benzylated D-glucopyranose acetates via acid-mediated simultaneous debenzylation-acetolysis [J].

Cao, Yang ;

Okada, Yasunori ;

Yamada, Hidetoshi .

CARBOHYDRATE RESEARCH, 2006, 341 (13) :2219-2223

[5] GLYCOCINNAMOYLSPERMIDINES, A NEW CLASS OF ANTIBIOTICS .3. - STRUCTURES OF LL-BM123BETA, GAMMA1, AND GAMMA2 [J].

ELLESTAD, GA ;

COSULICH, DB ;

BROSCHARD, RW ;

MARTIN, JH ;

KUNSTMANN, MP ;

MORTON, GO ;

LANCASTER, JE ;

FULMOR, W ;

LOVELL, FM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (08) :2515-2524

[6] Design and synthesis of new aminoglycoside antibiotics containing neamine as an optimal core structure: Correlation of antibiotic activity with in vitro inhibition of translation [J].

Greenberg, WA ;

Priestley, ES ;

Sears, PS ;

Alper, PB ;

Rosenbohm, C ;

Hendrix, M ;

Hung, SC ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6527-6541

[7] Probing the ribosomal RNA A-site with functionally diverse analogues of paromomycin - synthesis of ring I mimetics [J].

Hanessian, Stephen ;

Adhikari, Susanta ;

Szychowski, Janek ;

Pachamuthu, Kandasmy ;

Wang, Xiaojing ;

Migawa, Michael T. ;

Griffey, Richard H. ;

Swayze, Eric E. .

TETRAHEDRON, 2007, 63 (04) :827-846

[8] SYNTHESES WITH PARTIALLY BENZYLATED SUGARS .4. A ROUTE TO SOME 1-O-ACYL-2-ACYLAMIDO-2-DEOXY-D-GLUCOPYRANOSES AND -D-GALACTOPYRANOSES [J].

HARRISON, R ;

FLETCHER, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (07) :2317-&

[9] Direct observation of aminoglycoside-RNA interactions by surface plasmon resonance [J].

Hendrix, M ;

Priestley, ES ;

Joyce, GF ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (16) :3641-3648

[10] AN EFFECTIVE STRATEGY FOR THE SYNTHESIS OF 6-O-(2-AMINO-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL)-D-CHIRO AND D-MYO-INOSITOL 1-PHOSPHATE RELATED TO PUTATIVE INSULIN MIMETICS [J].

JARAMILLO, C ;

CHIARA, JL ;

MARTINLOMAS, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3135-3141

← 1 2 3 →