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Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues
Joint Authors
Lima, Tamires Cardoso
Bezerra, Daniel Pereira
Perez-Castillo, Yunierkis
Nóbrega, Flávio R.
Silva, Larisse V.
Bezerra Filho, Carlos da Silva M.
Lima, Tatjana K. Souza
de Sousa, Damião Pergentino
Source
Issue
Vol. 2019, Issue 2019 (31 Dec. 2019), pp.1-12, 12 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2019-01-08
Country of Publication
Egypt
No. of Pages
12
Main Subjects
Abstract EN
Piplartine is an alkamide found in different Piper species and possesses several biological activities, including antiparasitic properties.
Thus, the aim of the present study was to evaluate a series of 32 synthetic piplartine analogues against the Leishmania amazonensis promastigote forms and establish the structure-activity relationship and 3D-QSAR of these compounds.
The antileishmanial effect of the compounds was determined using the MTT method.
Most compounds were found to be active against L.
amazonensis.
Among 32 assayed derivatives, compound (E)-(−)-bornyl 3-(3,4,5-trimethoxyphenyl)-acrylate exhibited the most potent antileishmanial activity (IC50 = 0.007 ± 0.008 μM, SI > 10), followed by benzyl 3,4,5-trimethoxybenzoate (IC50 = 0.025 ± 0.009 μM, SI > 3.205) and (E)-furfuryl 3-(3,4,5-trimethoxyphenyl)-acrylate (IC50 = 0.029 ± 0.007 μM, SI > 2.688).
It was found that the rigid substituents contribute to increasing antiparasitic activity against L.
amazonensis promastigotes.
The presence of the unsaturated heterocyclic substituent in the phenylpropanoid chemical structure (furfuryl group) resulted in a bioactive derivative.
Molecular simplification of benzyl 3,4,5-trimethoxybenzoate by omitting the spacer group contributed to the bioactivity of this compound.
Furthermore, bornyl radical appears to be important for antileishmanial activity, since (E)-(−)-bornyl 3-(3,4,5-trimethoxyphenyl)-acrylate exhibited the most potent antileishmanial activity.
These results show that some derivatives studied would be useful as prototype molecules for the planning of new derivatives with profile of antileishmanial drugs.
American Psychological Association (APA)
Nóbrega, Flávio R.& Silva, Larisse V.& Bezerra Filho, Carlos da Silva M.& Lima, Tamires Cardoso& Perez-Castillo, Yunierkis& Bezerra, Daniel Pereira…[et al.]. 2019. Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues. Journal of Chemistry،Vol. 2019, no. 2019, pp.1-12.
https://search.emarefa.net/detail/BIM-1171107
Modern Language Association (MLA)
Nóbrega, Flávio R.…[et al.]. Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues. Journal of Chemistry No. 2019 (2019), pp.1-12.
https://search.emarefa.net/detail/BIM-1171107
American Medical Association (AMA)
Nóbrega, Flávio R.& Silva, Larisse V.& Bezerra Filho, Carlos da Silva M.& Lima, Tamires Cardoso& Perez-Castillo, Yunierkis& Bezerra, Daniel Pereira…[et al.]. Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues. Journal of Chemistry. 2019. Vol. 2019, no. 2019, pp.1-12.
https://search.emarefa.net/detail/BIM-1171107
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1171107