Phthalazine-triones: Calix[4]arene-assisted synthesis using green solvents and their anticancer activities against human cancer cells
Fourteen phthalazine-triones bearing different substituents at C-4 position were synthesized through multicomponent reactions (MCR) by using phthalhydrazide, dimedone and diferent aldehydes as starting materials, p-sulfonic acid calix[4]arene as catalyst and ethyl lactate as solvent under microwave...
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2019-12-01
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| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535216300314 |
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doaj-d8b8f702b82241d89e06f1607715ea4d2020-11-25T02:22:13ZengElsevierArabian Journal of Chemistry1878-53522019-12-0112840654073Phthalazine-triones: Calix[4]arene-assisted synthesis using green solvents and their anticancer activities against human cancer cellsYuri F. Rego0Cleiton M. da Silva1Daniel L. da Silva2Jeferson G. da Silva3Ana Lúcia T.G. Ruiz4João E. de Carvalho5Sergio A. Fernandes6Ângelo de Fátima7Grupo de Estudos em Química Orgânica e Biológica (GEQOB), Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilGrupo de Estudos em Química Orgânica e Biológica (GEQOB), Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilGrupo de Estudos em Química Orgânica e Biológica (GEQOB), Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Belo Horizonte, MG, BrazilDepartamento de Farmácia, Universidade Federal de Juiz de Fora, Campus Governador Valadares, MG, BrazilCentro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), Universidade Estadual de Campinas, Paulínia, SP, BrazilCentro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), Universidade Estadual de Campinas, Paulínia, SP, BrazilGrupo de Química Supramolecular e Biomimética (GQSB), Departamento de Química, Universidade Federal de Viçosa, Viçosa, MG, BrazilGrupo de Estudos em Química Orgânica e Biológica (GEQOB), Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil; Corresponding author. Tel.: +55 31 3409 6373; fax: +55 31 3409 5700.Fourteen phthalazine-triones bearing different substituents at C-4 position were synthesized through multicomponent reactions (MCR) by using phthalhydrazide, dimedone and diferent aldehydes as starting materials, p-sulfonic acid calix[4]arene as catalyst and ethyl lactate as solvent under microwave irradiation. Compounds 7–16 were obtained in excellent to moderate yields (94–51%) in only 10 min of reaction using this methodology. The antiproliferative activity against cancer cells was disclosed, for the first time, for synthesized compounds. The capacity of all compounds to inhibit cancer cells growth was dependent on the histological origin of cells. Compound 20 was active against more than one strain. Keywords: Catalysis, Green chemistry, Microwave assisted synthesis, Antiproliferative activity, p-Sulfonic acid calix[4]arenehttp://www.sciencedirect.com/science/article/pii/S1878535216300314 |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Yuri F. Rego Cleiton M. da Silva Daniel L. da Silva Jeferson G. da Silva Ana Lúcia T.G. Ruiz João E. de Carvalho Sergio A. Fernandes Ângelo de Fátima |
| spellingShingle |
Yuri F. Rego Cleiton M. da Silva Daniel L. da Silva Jeferson G. da Silva Ana Lúcia T.G. Ruiz João E. de Carvalho Sergio A. Fernandes Ângelo de Fátima Phthalazine-triones: Calix[4]arene-assisted synthesis using green solvents and their anticancer activities against human cancer cells Arabian Journal of Chemistry |
| author_facet |
Yuri F. Rego Cleiton M. da Silva Daniel L. da Silva Jeferson G. da Silva Ana Lúcia T.G. Ruiz João E. de Carvalho Sergio A. Fernandes Ângelo de Fátima |
| author_sort |
Yuri F. Rego |
| title |
Phthalazine-triones: Calix[4]arene-assisted synthesis using green solvents and their anticancer activities against human cancer cells |
| title_short |
Phthalazine-triones: Calix[4]arene-assisted synthesis using green solvents and their anticancer activities against human cancer cells |
| title_full |
Phthalazine-triones: Calix[4]arene-assisted synthesis using green solvents and their anticancer activities against human cancer cells |
| title_fullStr |
Phthalazine-triones: Calix[4]arene-assisted synthesis using green solvents and their anticancer activities against human cancer cells |
| title_full_unstemmed |
Phthalazine-triones: Calix[4]arene-assisted synthesis using green solvents and their anticancer activities against human cancer cells |
| title_sort |
phthalazine-triones: calix[4]arene-assisted synthesis using green solvents and their anticancer activities against human cancer cells |
| publisher |
Elsevier |
| series |
Arabian Journal of Chemistry |
| issn |
1878-5352 |
| publishDate |
2019-12-01 |
| description |
Fourteen phthalazine-triones bearing different substituents at C-4 position were synthesized through multicomponent reactions (MCR) by using phthalhydrazide, dimedone and diferent aldehydes as starting materials, p-sulfonic acid calix[4]arene as catalyst and ethyl lactate as solvent under microwave irradiation. Compounds 7–16 were obtained in excellent to moderate yields (94–51%) in only 10 min of reaction using this methodology. The antiproliferative activity against cancer cells was disclosed, for the first time, for synthesized compounds. The capacity of all compounds to inhibit cancer cells growth was dependent on the histological origin of cells. Compound 20 was active against more than one strain. Keywords: Catalysis, Green chemistry, Microwave assisted synthesis, Antiproliferative activity, p-Sulfonic acid calix[4]arene |
| url |
http://www.sciencedirect.com/science/article/pii/S1878535216300314 |
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