Iminecalix[4]arenes: Microwave-assisted synthesis, X-ray crystal structures, and anticandidal activity

In this study, six iminecalix[4]arenes were synthesized and the crystal structures of two of the iminecalix[4]arenes were also determined. Iminecalix[4]arene adopts a strongly pinched cone conformation with two upper rim substituents pointing toward and the other two pointing away from the aromatic...

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Main Authors: Cleiton M. da Silva, Danielle L. da Silva, Thais F.F. Magalhães, Rosemeire B. Alves, Maria A. de Resende-Stoianoff, Felipe T. Martins, Ângelo de Fátima
Format: Article
Language:English
Published: Elsevier 2019-12-01
Series:Arabian Journal of Chemistry
Online Access:http://www.sciencedirect.com/science/article/pii/S1878535216300910
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spelling doaj-73d09a50030e4c099442396a2aeec61a2020-11-25T01:35:13ZengElsevierArabian Journal of Chemistry1878-53522019-12-0112843654376Iminecalix[4]arenes: Microwave-assisted synthesis, X-ray crystal structures, and anticandidal activityCleiton M. da Silva0Danielle L. da Silva1Thais F.F. Magalhães2Rosemeire B. Alves3Maria A. de Resende-Stoianoff4Felipe T. Martins5Ângelo de Fátima6Grupo de Estudos em Química Orgânica e Biológica (GEQOB), Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos, 6627, Belo Horizonte, MG 31270-901, BrazilDepartamento de Microbiologia, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos, 6627, Belo Horizonte, MG 31270-901, BrazilDepartamento de Microbiologia, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos, 6627, Belo Horizonte, MG 31270-901, BrazilGrupo de Estudos em Química Orgânica e Biológica (GEQOB), Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos, 6627, Belo Horizonte, MG 31270-901, BrazilDepartamento de Microbiologia, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos, 6627, Belo Horizonte, MG 31270-901, BrazilInstituto de Química, Universidade Federal de Goiás, Campus Samambaia, CP 131, Goiânia, GO 74001-970, BrazilGrupo de Estudos em Química Orgânica e Biológica (GEQOB), Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos, 6627, Belo Horizonte, MG 31270-901, Brazil; Corresponding author. Fax: +55 31 3409 5700.In this study, six iminecalix[4]arenes were synthesized and the crystal structures of two of the iminecalix[4]arenes were also determined. Iminecalix[4]arene adopts a strongly pinched cone conformation with two upper rim substituents pointing toward and the other two pointing away from the aromatic cavity. This uncommon conformation is stabilized by an intramolecular π…π interaction between the phenyl rings from the upper rim substituents pointing inwards the cone. In addition, phenyl rings from the substituent groups are not coplanar with respect to the calixarene phenyl rings holding them. The compounds, as well as their respective monomeric units, were evaluated for their antifungal activities against Candida strains. All the synthesized iminecalix[4]arenes were found to cause higher inhibition of all tested Candida strains than their respective monomers. The ratio between the minimal inhibitory concentration (MIC) of a monomer and the corresponding iminecalix[4]arene ranged from 2.05 to 36.50. Furthermore, the iminecalix[4]arene bearing nitrofuran group exhibited low MIC values comparable to that of fluconazole. Thus, this compound was twice more active than fluconazole against Candida krusei. Keywords: Calix[4]arene, Aldimine, Iminecalix[4]arenes microwave-assisted synthesis, Antifungal activity, X-ray crystal structure, Pinched cone conformationhttp://www.sciencedirect.com/science/article/pii/S1878535216300910
collection DOAJ
language English
format Article
sources DOAJ
author Cleiton M. da Silva
Danielle L. da Silva
Thais F.F. Magalhães
Rosemeire B. Alves
Maria A. de Resende-Stoianoff
Felipe T. Martins
Ângelo de Fátima
spellingShingle Cleiton M. da Silva
Danielle L. da Silva
Thais F.F. Magalhães
Rosemeire B. Alves
Maria A. de Resende-Stoianoff
Felipe T. Martins
Ângelo de Fátima
Iminecalix[4]arenes: Microwave-assisted synthesis, X-ray crystal structures, and anticandidal activity
Arabian Journal of Chemistry
author_facet Cleiton M. da Silva
Danielle L. da Silva
Thais F.F. Magalhães
Rosemeire B. Alves
Maria A. de Resende-Stoianoff
Felipe T. Martins
Ângelo de Fátima
author_sort Cleiton M. da Silva
title Iminecalix[4]arenes: Microwave-assisted synthesis, X-ray crystal structures, and anticandidal activity
title_short Iminecalix[4]arenes: Microwave-assisted synthesis, X-ray crystal structures, and anticandidal activity
title_full Iminecalix[4]arenes: Microwave-assisted synthesis, X-ray crystal structures, and anticandidal activity
title_fullStr Iminecalix[4]arenes: Microwave-assisted synthesis, X-ray crystal structures, and anticandidal activity
title_full_unstemmed Iminecalix[4]arenes: Microwave-assisted synthesis, X-ray crystal structures, and anticandidal activity
title_sort iminecalix[4]arenes: microwave-assisted synthesis, x-ray crystal structures, and anticandidal activity
publisher Elsevier
series Arabian Journal of Chemistry
issn 1878-5352
publishDate 2019-12-01
description In this study, six iminecalix[4]arenes were synthesized and the crystal structures of two of the iminecalix[4]arenes were also determined. Iminecalix[4]arene adopts a strongly pinched cone conformation with two upper rim substituents pointing toward and the other two pointing away from the aromatic cavity. This uncommon conformation is stabilized by an intramolecular π…π interaction between the phenyl rings from the upper rim substituents pointing inwards the cone. In addition, phenyl rings from the substituent groups are not coplanar with respect to the calixarene phenyl rings holding them. The compounds, as well as their respective monomeric units, were evaluated for their antifungal activities against Candida strains. All the synthesized iminecalix[4]arenes were found to cause higher inhibition of all tested Candida strains than their respective monomers. The ratio between the minimal inhibitory concentration (MIC) of a monomer and the corresponding iminecalix[4]arene ranged from 2.05 to 36.50. Furthermore, the iminecalix[4]arene bearing nitrofuran group exhibited low MIC values comparable to that of fluconazole. Thus, this compound was twice more active than fluconazole against Candida krusei. Keywords: Calix[4]arene, Aldimine, Iminecalix[4]arenes microwave-assisted synthesis, Antifungal activity, X-ray crystal structure, Pinched cone conformation
url http://www.sciencedirect.com/science/article/pii/S1878535216300910
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