Synthesis, Leishmanicidal Activity and Theoretical Evaluations of a Series of Substituted bis-2-Hydroxy-1,4-Naphthoquinones

被引：38
作者：
de Araujo, Morgana V. [1 ]
de Souza, Patricia S. O. [2 ]
de Queiroz, Aline C. [1 ]
da Matta, Carolina B. B. [1 ]
Leite, Anderson Brandao [1 ]
da Silva, Amanda Evelyn [1 ]
de Franca, Jose A. A. [2 ]
Silva, Tania M. S. [2 ]
Camara, Celso A. [2 ]
Alexandre-Moreira, Magna S. [1 ]
机构：
[1] Univ Fed Alagoas, Inst Biol Sci & Hlth, Lab Pharmacol & Immun, BR-57020720 Maceio, AL, Brazil
[2] Univ Fed Rural Pernambuco, Dept Mol Sci, Lab Bioact Cpds Synth, BR-52171900 Recife, PE, Brazil
来源：
MOLECULES | 2014年 / 19卷 / 09期
关键词：
naphthoquinones; knoevenagel; bis-2-hydroxy-1,4-naphthoquinones; antileishmanial activity; Leishmania braziliensis; Leishmania amazonensis; BETA-LAPACHONE; ANTILEISHMANIAL ACTIVITY; EFFICIENT SYNTHESIS; NAPHTHOQUINONES; DERIVATIVES; INHIBITION; CHEMISTRY;
D O I：
10.3390/molecules190915180
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：
A series of eight substituted bis-2-hydroxy-1,4-naphthoquinone derivatives was synthesized through lawsone condensation with various aromatic and aliphatic aldehydes under mild acidic conditions. The title compounds were evaluated for antileishmanial activity in vitro against Leishmania amazonensis and Leishmania braziliensis promastigotes; six compounds showed good activity without significant toxic effects. The compound with the highest activity was used for an in vivo assay with Leishmania amazonensis.
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收藏
页码：15180 / 15195
页数：16
相关论文
共 37 条
[1]   Structure/Antileishmanial Activity Relationship Study of Naphthoquinones and Dependency of the Mode of Action on the Substitution Patterns [J].
Ali, Ahmad ;
Assimopoulou, Andreana Nikolaos ;
Papageorgiou, Vassilios Peter ;
Kolodziej, Herbert .
PLANTA MEDICA, 2011, 77 (18) :2003-2012
[2]  
Antunes Rossana M. Pessoa, 2006, Rev. bras. farmacogn., V16, P517, DOI 10.1590/S0102-695X2006000400014
[3]   Growth inhibitory effects of 3′-nitro-3-phenylamino nor-beta-lapachone against HL-60: A redox-dependent mechanism [J].
Araujo, A. J. ;
de Souza, A. A. ;
da Silva Junior, E. N. ;
Marinho-Filho, J. D. B. ;
de Moura, M. A. B. F. ;
Rocha, D. D. ;
Vasconcellos, M. C. ;
Costa, C. O. ;
Pessoa, C. ;
de Moraes, M. O. ;
Ferreira, V. F. ;
de Abreu, F. C. ;
Pinto, A. V. ;
Montenegro, R. C. ;
Costa-Lotufo, L. V. ;
Goulart, M. O. F. .
TOXICOLOGY IN VITRO, 2012, 26 (04) :585-594
[4]   New 1,2,3,4-tetrahydro-1-aza-anthraquinones and 2-aminoalkyl compounds from norlapachol with molluscicidal activity [J].
Barbosa, TP ;
Camara, CA ;
Silva, TMS ;
Martins, RM ;
Pinto, AC ;
Vargas, MD .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (23) :6464-6469
[5]   Studies on quinones. Part 42: Synthesis of furylquinone and hydroquinones with antiproliferative activity against human tumor cell lines [J].
Benites, Julio ;
Valderrama, Jaime A. ;
Rivera, Felipe ;
Rojo, Leonel ;
Campos, Nair ;
Pedro, Madalena ;
Jose Nascimento, Maria Saeo .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (02) :862-868
[6]  
Bock K., 1986, J CHEM SOC P1, V1986, P659
[7]   THE ACTIVITY OF PLUMBAGIN AND OTHER ELECTRON CARRIERS AGAINST LEISHMANIA-DONOVANI AND LEISHMANIA-MEXICANA-AMAZONENSIS [J].
CROFT, SL ;
EVANS, AT ;
NEAL, RA .
ANNALS OF TROPICAL MEDICINE AND PARASITOLOGY, 1985, 79 (06) :651-653
[8]   THE ACTIVITY OF HYDROXYNAPHTHOQUINONES AGAINST LEISHMANIA-DONOVANI [J].
CROFT, SL ;
HOGG, J ;
GUTTERIDGE, WE ;
HUDSON, AT ;
RANDALL, AW .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 1992, 30 (06) :827-832
[9]   On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions [J].
da Silva Junior, Eufranio N. ;
de Melo, Isadora M. M. ;
Diogo, Emilay B. T. ;
Costa, Verenice A. ;
de Souza Filho, Jose D. ;
Valenca, Wagner O. ;
Camara, Celso A. ;
de Oliveira, Ronaldo N. ;
de Araujo, Alexandre S. ;
Emery, Flavio S. ;
dos Santos, Marcelo R. ;
de Simone, Carlos A. ;
Menna-Barreto, Rubem F. S. ;
de Castro, Solange L. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 52 :304-312
[10]   An overview of the chemistry and pharmacology of naphthoquinones with emphasis on β-lapachone and derivatives. [J].
da Silva, MN ;
Ferreira, VF ;
de Souza, MCBV .
QUIMICA NOVA, 2003, 26 (03) :407-416
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