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A Dimroth rearrangement approach for the synthesis of selenopheno[2,3-e][1,2,4]triazolo[1,5-c]pyrimidines with cytotoxic activity on breast cancer cells.
Kohandel, Omid; Sheikhi-Mohammareh, Seddigheh; Oroojalian, Fatemeh; Memariani, Toktam; Mague, Joel; Shiri, Ali.
Afiliación
  • Kohandel O; Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran.
  • Sheikhi-Mohammareh S; Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran.
  • Oroojalian F; Department of Advanced Sciences and Technologies, School of Medicine, North Khorasan University of Medical Sciences, Bojnurd, Iran.
  • Memariani T; Natural Products and Medicinal Plants Research Center, North Khorasan University of Medical Sciences, Bojnurd, Iran.
  • Mague J; Natural Products and Medicinal Plants Research Center, North Khorasan University of Medical Sciences, Bojnurd, Iran.
  • Shiri A; Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA.
Mol Divers ; 26(3): 1621-1633, 2022 Jun.
Article en En | MEDLINE | ID: mdl-34357512
New selenopheno[2,3-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives have been synthesized via Dimroth rearrangement by cyclocondensation of 7-cyano-4-hydrazinyl-6-(pyrrolidin-1-yl)selenopheno[3,2-d]pyrimidine with electrophilic carbons of either orthoesters in acetic acid or carbon disulfide in pyridine followed by S-alkylation. All the newly synthesized products have been structurally elucidated. The in vitro anticancer screening of the tricyclic Se-containing heterocycles was accomplished against human breast carcinoma MCF-7 cancerous cell line and L929 cells. Anticancer results revealed that the S-hexyl-substituted compound with an IC50 value of 158.9 µM in 72 h was foremost among others in cytotoxic potency. In the following order, S-pentyl and S-ethyl-substituted derivatives with IC50 values of 216.1 and 396.5 µM were second and third efficient compounds as in anticancer activity, respectively. The inhibitory effects of the mentioned compounds were less on the growth of L929 cells.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Neoplasias de la Mama / Antineoplásicos Límite: Female / Humans Idioma: En Revista: Mol Divers Asunto de la revista: BIOLOGIA MOLECULAR Año: 2022 Tipo del documento: Article País de afiliación: Irán Pais de publicación: Países Bajos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Neoplasias de la Mama / Antineoplásicos Límite: Female / Humans Idioma: En Revista: Mol Divers Asunto de la revista: BIOLOGIA MOLECULAR Año: 2022 Tipo del documento: Article País de afiliación: Irán Pais de publicación: Países Bajos