A concise synthesis and antimicrobial activities of 3-polyamino-23,24-bisnorcholanes as steroid-polyamine conjugates

被引：9

作者：

Kim, Hong-Seok ^{[1
]}

Khan, Sharaf N. ^{[1
]}

Jadhav, Jyoti R. ^{[1
]}

Jeong, Ji-Woong ^{[2
]}

Jung, Kyungjin ^{[2
]}

Kwak, Jin-Hwan ^{[2
]}

机构：

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

[2] Handong Global Univ, Sch Life Sci, Pohang 791708, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 13期

关键词：

Steroid-polyamine conjugate; SAR; Reductive amination; Antimicrobial activity; STEREOSELECTIVE-SYNTHESIS; REDUCTIVE AMINATION; 2-DIMENSIONAL NMR; FORMAL SYNTHESIS; POLYMYXIN-B; SQUALAMINE; DNA; DESIGN; ANTIBIOTICS; DERIVATIVES;

D O I：

10.1016/j.bmcl.2011.05.048

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of steroid-polyamine conjugates were synthesized and evaluated for their antimicrobial activity. This study was focused on the effect of stereochemistry at the C-3 and C-5 of steroids and types of polyamine at C-3 on activity against various human pathogens. All the conjugates exhibited strong antimicrobial activities against Gram-positive strains. Compound 18 was found to be the most potent in these series with a MIC value as low as 1 mu g/mL against the bacterium Staphylococcus aureus ATCC6538P. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3861 / 3865

页数：5

共 55 条

[1] Design and synthesis of bile acid-based amino sterols as antimicrobial agents [J].

Aher, Nilkanth G. ;

Pore, Vandana S. ;

Mishra, Nripendra N. ;

Shukla, Praveen K. ;

Gonnade, Rajesh G. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (18) :5411-5414

[2]

Ahmad MW, 2009, B KOREAN CHEM SOC, V30, P2101

[3]

Bhattacharjya S, 1997, BIOPOLYMERS, V41, P251, DOI 10.1002/(SICI)1097-0282(199703)41:3<251::AID-BIP2>3.0.CO

[4]

2-R

[5] The "triamino-analogue'' of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry [J].

Bhattarai, Khadga M. ;

del Amo, Vicente ;

Magro, Germinal ;

Sisson, Adam L. ;

Joos, Jean-Baptiste ;

Charmant, Jonathan P. H. ;

Kantacha, Anob ;

Davis, Anthony P. .

CHEMICAL COMMUNICATIONS, 2006, (22) :2335-2337

[6]

Blagbrough Ian S., 1999, Pharmacy and Pharmacology Communications, V5, P139

[7] Asymmetric intercalation of N1-(acridin-9-ylcarbonyl)spermine at homopurine sites of duplex DNA [J].

Blagbrough, IS ;

Taylor, S ;

Carpenter, ML ;

Novoselskiy, V ;

Shamma, T ;

Haworth, IS .

CHEMICAL COMMUNICATIONS, 1998, (08) :929-930

[8] Polyamines and novel polyamine conjugates interact with DNA in ways that can be exploited in non-viral gene therapy [J].

Blagbrough, IS ;

Geall, AJ ;

Neal, AP .

BIOCHEMICAL SOCIETY TRANSACTIONS, 2003, 31 :397-406

[9]

BLAGBROUGH IS, 2002, BIOM HLTH R, V55, P64

[10] Higher-order structure of polymyxin B: The functional significance of topological flexibility [J].

Bruch, MD ;

Cajal, Y ;

Koh, JT ;

Jain, MK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :11993-12004

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