Synthesis and biological evaluation of a new series of N-acyldiamines as potential antibacterial and antifungal agents

被引：12

作者：

Ferreira, Bianca da S. ^{[1
]}

de Almeida, Angelina M. ^{[1
]}

Nascimento, Thiago C. ^{[2
]}

de Castro, Pedro P. ^{[2
]}

Silva, Vania L. ^{[2
]}

Diniz, Claudio G. ^{[2
]}

Le Hyaric, Mireille ^{[1
]}

机构：

[1] Univ Fed Juiz de Fora, ICE, Dept Quim, BR-36036330 Juiz De Fora, MG, Brazil

[2] Univ Fed Juiz de Fora, ICE, Dept Parasitol Microbiol & Imunol, BR-36036330 Juiz De Fora, MG, Brazil

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 19期

关键词：

N-Acyldiamines; Antibacterial; Antifungal; MRSA; Lipophilicity; FATTY-ACIDS; ANTIMICROBIAL ACTIVITY; DERIVATIVES;

D O I：

10.1016/j.bmcl.2014.08.047

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In continuation of our efforts to find new antimicrobial compounds, series of fatty N-acyldiamines were prepared from fatty methyl esters and 1,2-ethylenediamine, 1,3-propanediamine or 1,4-butanediamine. The synthesized compounds were screened for their antibacterial activity against Gram-positive bacteria (Staphylococcus aureus, Staphylococcus epidermidis), Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and for their antifungal activity against four species of Candida (C. albicans, C. tropicalis, C. glabrata and C. parapsilosis). Compounds 5a (N-(2-aminoethyl)dodecanamide), 5b (N-(2-aminoethyl)tetracanamide) and 6d (N-(3-aminopropyl)oleamide) were the most active against Gram-positive bacteria, with MIC values ranging from 1 to 16 mu g/mL and were evaluated for their activity against 21 clinical isolates of methicillin-resistant S. aureus. All the compounds exhibited good to moderate antifungal activity. Compared to chloramphenicol, compound 6b displayed a similar activity (MIC50 = 16 mu g/mL). A positive correlation could be established between lipophilicity and biological activity. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：4626 / 4629

页数：4

共 16 条

[1]

Almeida C G, 2009, BIOMED PHARMACOTHER, V64, P287

[2]

[Anonymous], 2008, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts

[3]

Approved Standard, VThird

[4]

CLSI, 2007, M100S16 CLSI, V26

[5] Antileishmanial activity of aldonamides and N-acyl-diamine derivatives [J].

Coimbra, Elaine S. ;

Almeida, Camila G. ;

Junior, Wilson V. ;

Dos Reis, Roberta C. N. ;

De Almeida, Ana C. F. ;

Forezi, Luana S. M. ;

De Almeida, Mauro V. ;

Le Hyaric, Mireille .

THESCIENTIFICWORLDJOURNAL, 2008, 8 :752-756

[6] Synthesis and antimicrobial activity of novel amphiphilic aromatic amino alcohols [J].

de Almeida, Angelina M. ;

Nascimento, Thiago ;

Ferreira, Bianca S. ;

de Castro, Pedro P. ;

Silva, Vania L. ;

Diniz, Claudio G. ;

Le Hyaric, Mireille .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (10) :2883-2887

[7]

De Almeida M. V., 2008, J BRAZIL CHEM SOC, V19, P1065

[8] Antibacterial free fatty acids: activities, mechanisms of action and biotechnological potential [J].

Desbois, Andrew P. ;

Smith, Valerie J. .

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2010, 85 (06) :1629-1642

[9]

Deutsche Veterinarmedizinische Gesellschaft, 1977, RICHTL PRUF CHEM DES, V47

[10] Arachidonic acid increases antifungal susceptibility of Candida albicans and Candida dubliniensis [J].

Ells, Ruan ;

Kock, Johan L. F. ;

Van Wyk, Pieter W. J. ;

Botes, Piet J. ;

Pohl, Carolina H. .

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2009, 63 (01) :124-128

← 1 2 →