A Simple and Efficient Protocol for the Knoevenagel Reaction of Benzylidenemalononitriles and the Evaluation of the Larvicidal Activity on Aedes Aegypti

被引：8

作者：

Carvalho, Harlyson L. ^{[1
]}

de Amorim, Andreia L. ^{[1
]}

Araujo, Inana F. ^{[1
,2
]}

Marino, Bianca L. B. ^{[3
]}

Jimenez, David E. Q. ^{[4
]}

Ferreira, Ricardo M. A. ^{[2
]}

Hage-Melim, Lorane I. S. ^{[3
]}

Souto, Raimundo N. P. ^{[2
]}

Porto, Andre L. M. ^{[4
]}

Ferreira, Irlon M. ^{[1
]}

机构：

[1] Univ Fed Amapa, Grp Biocatalise & Biotransformacao Quim Organ, Colegiado Quim, Rod JK,KM 02, BR-68902280 Macapa, Amapa, Brazil

[2] Univ Fed Amapa, Lab Artropodes, Colegiado Biol, Rod JK,KM 02, BR-68902280 Macapa, Amapa, Brazil

[3] Univ Fed Amapa, Lab Quim Farmaceut & Med, Rod JK,KM 02, BR-68902280 Macapa, Amapa, Brazil

[4] Univ Sao Paulo, Lab Quim Organ & Biocatalise, Inst Quim Sao Carlos, Av Joao Dagnone,1100,Ed Quimica Ambiental, BR-13563120 Sao Carlos, SP, Brazil

来源：

REVISTA VIRTUAL DE QUIMICA | 2018年 / 10卷 / 02期

关键词：

Aedes aegypti; Green chemistry; Larvicidal activity; Molecular docking;

D O I：

10.21577/1984-6835.20180028

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Mosquitoes of the genus Aedes are responsible for dengue, yellow fever, chikungunya and Zika. Although important advances have emerged in the development of alternative methods for mosquito control, chemical insecticides remain a vital part of integrated control programs. In this paper were synthetized benzylidenemalononitrile derivatives in good yields (71-99%) using only water and glycerol at room temperature. A study of the larvicidal activity between benzylidenemalononitriles showed that the compound 2e (R= 4-Cl) possesses excellent larvicidal activity (LC50 and LC90 of 9.42 and 15.02, respectively at 24 h). A study of molecular docking was applied to identify the type of interaction of compound 2e with binding sites at the enzyme acetylcholinesterase. The profile of the interaction showed a score 48.9795 with five bonds at three different amino acids.

引用

页码：362 / 374

页数：13

共 35 条

[1] Binary combinations of organophosphorus and synthetic pyrethroids are more potent acetylcholinesterase inhibitors than organophosphorus and carbamate mixtures: An in vitro assessment [J].

Arora, Sumitra ;

Balotra, Sahil ;

Pandey, Gunjan ;

Kumar, Anu .

TOXICOLOGY LETTERS, 2017, 268 :8-16

[2]

Bharathi A., 2014, BIOMEDICAL RES INT, V2014, P2

[3] GENETIC MANIPULATION OF INSECT VECTORS AS A STRATEGY FOR THE CONTROL OF VECTOR-BORNE DISEASE [J].

CRAMPTON, JM ;

WARREN, A ;

LYCETT, GJ ;

HUGHES, MA ;

COMLEY, IP ;

EGGLESTON, P .

ANNALS OF TROPICAL MEDICINE AND PARASITOLOGY, 1994, 88 (01) :3-12

[4] Thiosemicarbazones as Aedes aegypti larvicidal [J].

da Silva, Joao Bosco P. ;

Navarro, Daniela Maria do A. F. ;

da Silva, Aluizio G. ;

Santos, Geanne K. N. ;

Dutra, Kamilla A. ;

Moreira, Diogo Rodrigo ;

Ramos, Mozart N. ;

Espindola, Jose Wanderlan P. ;

de Oliveira, Ana Daura T. ;

Brondani, Dalci Jose ;

Leite, Ana Cristina L. ;

Hernandes, Marcelo Zaldini ;

Pereira, Valeria R. A. ;

da Rocha, Lucas F. ;

de Castro, Maria Carolina A. B. ;

de Oliveira, Beatriz C. ;

Lan, Que ;

Merz, Kenneth M., Jr. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 100 :162-175

[5] Knoevenagel Condensation of Aldehydes and Ketones with Malononitrile Catalyzed by Amine Compounds-Tethered Fe3O4@SiO2 Nanoparticles [J].

de Resende Filho, Joao Batista M. ;

Pires, Gilvan P. ;

Gomes de Oliveira Ferreira, Joao Marcos ;

Teotonio, Ercules E. S. ;

Vale, Juliana A. .

CATALYSIS LETTERS, 2017, 147 (01) :167-180

[6] Chikungunya Virus and Aedes Mosquitoes: Saliva Is Infectious as soon as Two Days after Oral Infection [J].

Dubrulle, Mathieu ;

Mousson, Laurence ;

Moutailler, Sara ;

Vazeille, Marie ;

Failloux, Anna-Bella .

PLOS ONE, 2009, 4 (06)

[7] Lessons in molecular recognition: The effects of ligand and protein flexibility on molecular docking accuracy [J].

Erickson, JA ;

Jalaie, M ;

Robertson, DH ;

Lewis, RA ;

Vieth, M .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (01) :45-55

[8] ULTRASOUND-PROMOTED RAPID AND EFFICIENT IODINATION OF AROMATIC AND HETEROAROMATIC COMPOUNDS IN THE PRESENCE OF IODINE AND HYDROGEN PEROXIDE IN WATER [J].

Ferreira, Irlon M. ;

Casagrande, Gleison A. ;

Pizzuti, Lucas ;

Raminelli, Cristiano .

SYNTHETIC COMMUNICATIONS, 2014, 44 (14) :2094-2102

[9] Efficient and eco-friendly synthesis of iodinated aromatic building blocks promoted by iodine and hydrogen peroxide in water: a mechanistic investigation by mass spectrometry [J].

Gallo, Rafael D. C. ;

Ferreira, Irlon M. ;

Casagrande, Gleison A. ;

Pizzuti, Lucas ;

Oliveira-Silva, Diogo ;

Raminelli, Cristiano .

TETRAHEDRON LETTERS, 2012, 53 (40) :5372-5375

[10]

Gupta S., 2014, BIOMED RES INT, V2014, P1, DOI DOI 10.1155/2014/93201725050379

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