Synthesis and antimicrobial activity of squalamine analogue

被引：59

作者：

Kim, HS ^{[1
]}

Choi, BS

Kwon, KC

Lee, SO

Kwak, HJ

Lee, CH

机构：

[1] Kyungpook Natl Univ, Dept Ind Chem, Taegu 702701, South Korea

[2] Korea Res Inst Chem Technol, Div Bioorgan, Taejon 305600, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2000年 / 8卷 / 08期

关键词：

D O I：

10.1016/S0968-0896(00)00128-0

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Synthesis and antimicrobial activity of squalamine analogue 2 are reported. The synthesis of 2 was accomplished from bisnoralcohol 3. The spermidine moiety was introduced via reductive amination of an appropriately functionalized 3 beta-aminosterol with spermidinyl aldehyde 17 utilizing sodium triacetoxyborohydride as the reducing agent. Compound 2 shows weaker antimicrobial activity than squalamine. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2059 / 2065

页数：7

共 19 条

[1] EPIDEMIOLOGY OF DRUG-RESISTANCE - IMPLICATIONS FOR A POSTANTIMICROBIAL ERA [J].

COHEN, ML .

SCIENCE, 1992, 257 (5073) :1050-1055

[2] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF HYDROXY STEROIDS [J].

EGGERT, H ;

VANANTWERP, CL ;

BHACCA, NS ;

DJERASSI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (01) :71-78

[3] The synthesis and characterization of analogs of the antimicrobial compound squalamine: 6 beta-hydroxy-3-aminosterols synthesized from hyodeoxycholic acid [J].

Jones, SR ;

Kinney, WA ;

Zhang, XH ;

Jones, LM ;

Selinsky, BS .

STEROIDS, 1996, 61 (10) :565-571

[4] Efficient route to 7α-(benzoyloxy)-3-dioxolane cholestan-24(R)-ol, a key intermediate in the synthesis of squalamine [J].

Jones, SR ;

Selinsky, BS ;

Rao, MN ;

Zhang, XH ;

Kinney, WA ;

Tham, FS .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3786-3789

[5] Antimicrobial activities of squalamine mimics [J].

Kikuchi, K ;

Bernard, EM ;

Sadownik, A ;

Regen, SL ;

Armstrong, D .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 41 (07) :1433-1438

[6] Synthesis of two marine natural products: The aglycones of pavoninin-1 and 2 [J].

Kim, HS ;

Kim, IC ;

Lee, SO .

TETRAHEDRON, 1997, 53 (24) :8129-8136

[7] Hydride reagents for stereoselective reductive amination. An improved preparation of 3-endo-tropanamine [J].

McGill, JM ;

LaBell, ES ;

Williams, M .

TETRAHEDRON LETTERS, 1996, 37 (23) :3977-3980

[8] A ruthenium catalyzed oxidation of steroidal alkenes to enones [J].

Miller, RA ;

Li, WJ ;

Humphrey, GR .

TETRAHEDRON LETTERS, 1996, 37 (20) :3429-3432

[9] SQUALAMINE - AN AMINOSTEROL ANTIBIOTIC FROM THE SHARK [J].

MOORE, KS ;

WEHRLI, S ;

RODER, H ;

ROGERS, M ;

FORREST, JN ;

MCCRIMMON, D ;

ZASLOFF, M .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (04) :1354-1358

[10] SYNTHESIS OF SQUALAMINE - A STEROIDAL ANTIBIOTIC FROM THE SHARK [J].

MORIARTY, RM ;

TULADHAR, SM ;

GUO, L ;

WEHRLI, S .

TETRAHEDRON LETTERS, 1994, 35 (44) :8103-8106

← 1 2 →