English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Curcumin inspired synthesis of unsymmetrical diarylpentanoids with highly potent anti-parasitic activities

Din, Z. U., Santos, A. d., Trapp, M. A., Lazarin-Bidóia, D., Garcia, F. P., Peron, F., et al. (2016). Curcumin inspired synthesis of unsymmetrical diarylpentanoids with highly potent anti-parasitic activities. Medicinal Chemistry Communications, 7, 820-831. doi:10.1039/C5MD00599J.

Item is

Basic

show hide
Genre: Journal Article

Files

show Files
hide Files
:
EXT565.pdf (Publisher version), 3MB
 
File Permalink:
-
Name:
EXT565.pdf
Description:
-
Visibility:
Restricted (Max Planck Institute for Chemical Ecology, MJCO; )
MIME-Type / Checksum:
application/pdf
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-
:
EXT565s1.pdf (Supplementary material), 5MB
 
File Permalink:
-
Name:
EXT565s1.pdf
Description:
-
Visibility:
Restricted (Max Planck Institute for Chemical Ecology, MJCO; )
MIME-Type / Checksum:
application/pdf
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-

Locators

show

Creators

show
hide
 Creators:
Din, Zia Ud, Author
Santos, Alef dos, Author
Trapp, Marilia A.1, Author              
Lazarin-Bidóia, Danielle, Author
Garcia, Francielle Pelegrin, Author
Peron, Francieli, Author
Nakamura, Celso Vataru, Author
Rodrigues-Filho, Edson, Author
Affiliations:
1External Organizations, ou_persistent22              

Content

show
hide
Free keywords: -
 Abstract: Unsymmetrical diarylpentanoid analogues of curcumin have been synthesized by Claisen–Schmidt condensation of different aldehydes and ketones. Anisaldehyde treated with 2-butanone and chlorobenzaldehyde with 2-pentanone resulted in intermediate compounds 1 and 2. Intermediate compounds 1 and 2 yield compounds 3–21 by treating them with different aldehydes having electron donating (methoxyl) and electron withdrawing (halogens and nitro) moieties. All compounds were evaluated for antiproliferative activity, particularly for the promastigote form of L. amazonensis and the epimastigote and trypomastigote forms of T. cruzi. The results revealed that these curcuminoid analogues have potency against parasites. Among 21 compounds, six were more potent than benznidazole for the epimastigote form, while 14 compounds were more potent for the trypomastigote form of T. cruzi. The binding interactions of all compounds were confirmed through molecular docking computational studies. Potent compounds showed very good interactions with the enzyme trypanothione reductase (PDB code 1BZL). DFT calculation helped us to understand the best possible conformation and optimized the structure. Our synthesized compounds can further be studied to develop lead compounds to treat parasitic diseases.

Details

show
hide
Language(s):
 Dates: 2016-01-232016-01-28
 Publication Status: Published online
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: Other: EXT565
DOI: 10.1039/C5MD00599J
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Medicinal Chemistry Communications
  Abbreviation : MedChemComm
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: (United Kingdom : Royal Society of Chemistry
Pages: - Volume / Issue: 7 Sequence Number: - Start / End Page: 820 - 831 Identifier: ISSN: 2040-2503
CoNE: https://pure.mpg.de/cone/journals/resource/2040-2503