Synthesis and antibacterial activities of cadiolides A, B and C and analogues

被引:20
作者
Boulange, Agathe [1 ,2 ]
Parraga, Javier [3 ]
Galan, Abraham [3 ]
Cabedo, Nuria [3 ,4 ]
Leleu, Stephane [1 ,2 ]
Jesus Sanz, Maria [5 ,6 ]
Cortes, Diego [3 ]
Franck, Xavier [1 ,2 ]
机构
[1] Normandie Univ, COBRA, UMR 6014, F-76821 Mont St Aignan, France
[2] Univ Rouen, CNRS, FR 3038, INSA Rouen, F-76821 Mont St Aignan, France
[3] Univ Valencia, Fac Farm, Dept Farmacol, Valencia 46100, Spain
[4] Univ Politecn Valencia, Inst Agroforestal Mediterraneo, Ctr Ecol Quim Agr, Valencia 46022, Spain
[5] Univ Valencia, Fac Med, Dept Farmacol, Valencia 46010, Spain
[6] Univ Clin Hosp Valencia, Inst Hlth Res INCLIVA, Valencia 46010, Spain
关键词
Cadiolides; Antibacterial; Butenolides; Multicomponent; Natural products; ASCIDIAN SYNOICUM SP; ANTIBIOTIC-RESISTANCE; ANTIMICROBIAL AGENTS; RUBROLIDES; TUNICATE; METABOLITES; APOPTOSIS; FURANONE; CELLS;
D O I
10.1016/j.bmc.2015.04.010
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
The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3618 / 3628
页数:11
相关论文
共 30 条
[1]   Inhibition of Candida albicans isocitrate lyase activity by cadiolides and synoilides from the ascidian Synoicum sp. [J].
Ahn, Chan-Hong ;
Won, Tae Hyung ;
Kim, Heegyu ;
Shin, Jongheon ;
Oh, Ki-Bong .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (14) :4099-4101
[2]   Short and efficient synthesis of cadiolide B [J].
Boukouvalas, J ;
Pouliot, M .
SYNLETT, 2005, (02) :343-345
[3]   Step-Economical Synthesis of the Marine Ascidian Antibiotics Cadiolide A, B, and D [J].
Boukouvalas, John ;
Thibault, Charles .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01) :681-684
[4]   Diastereoselective IBX Oxidative Dearomatization of Phenols by Remote Induction: Towards the Epicocconone Core Framework [J].
Boulange, Agathe ;
Peixoto, Philippe A. ;
Franck, Xavier .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (37) :10241-10245
[5]  
Clinical and Laboratory Standards Institute, 2006, M7A7 CLSI
[6]   Plant products as antimicrobial agents [J].
Cowan, MM .
CLINICAL MICROBIOLOGY REVIEWS, 1999, 12 (04) :564-+
[7]   Antibiotic resistance is ancient [J].
D'Costa, Vanessa M. ;
King, Christine E. ;
Kalan, Lindsay ;
Morar, Mariya ;
Sung, Wilson W. L. ;
Schwarz, Carsten ;
Froese, Duane ;
Zazula, Grant ;
Calmels, Fabrice ;
Debruyne, Regis ;
Golding, G. Brian ;
Poinar, Hendrik N. ;
Wright, Gerard D. .
NATURE, 2011, 477 (7365) :457-461
[8]   Novel isoquinoline derivatives as antimicrobial agents [J].
Galan, Abraham ;
Moreno, Laura ;
Parraga, Javier ;
Serrano, Angel ;
Jesus Sanz, Ma ;
Cortes, Diego ;
Cabedo, Nuria .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (11) :3221-3230
[9]   Involvement of oxygen radicals in cytarabine-induced apoptosis in human polymorphonuclear cells [J].
Iacobini, M ;
Menichelli, A ;
Palumbo, G ;
Multari, G ;
Werner, B ;
Del Principe, D .
BIOCHEMICAL PHARMACOLOGY, 2001, 61 (08) :1033-1040
[10]   Ultrafast time-resolved transient absorption and resonance Raman spectroscopy study of the photodeprotection and rearrangement reactions of p-hydroxyphenacyl caged phosphates [J].
Ma, CS ;
Kwok, WM ;
Chan, WS ;
Du, Y ;
Kan, JTW ;
Toy, PH ;
Phillips, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2558-2570