European Journal of Medicinal Chemistry p. 1093 - 1104 (2016)
Update date:2022-08-04
Topics:
Barbosa, Valéria Aquilino
Baréa, Paula
Mazia, Renata Sespede
Ueda-Nakamura, Tania
Costa, Willian Ferreira da
Foglio, Mary Ann
Goes Ruiz, Ana Lucia T.
Carvalho, Jo?o Ernesto de
Vendramini–Costa, Débora Barbosa
Nakamura, Celso Vataru
Sarragiotto, Maria Helena
A series of novel hybrids β-carboline-4-thiazolidinones were synthesized and evaluated for their in vitro antitumor activity against human cancer cell lines and for antiviral activity towards Herpes simplex virus type-1 (HSV-1). From the N′-(2-ylidene-4-thiazolidinone)-β-carboline-3-carbohydrazide series (9–11), compounds 9c and 11d were the most active, showing growth inhibition 50% (GI50) values less than 5 μM for all cell lines tested. Compound 9c, bearing the 4-dimethylaminophenyl group at C-1 of β-carboline was selected for further investigation concerning cell death and cell cycle profile, focusing on the human renal adenocarcinoma cell line 786-0. Treatments with 25 μM of compound 9c induced cell death after 15 h of treatment, characterized by phosphatidylserine exposure and loss of membrane integrity. Moreover, treatment with 12.5 μM promoted a sub-G1 arrest, which indicates cell death. Derivatives of the N-(2-substituted-aryl-4-thiazolidinone)-β-carboline-3-carboxamide series (18–23) showed a potent activity and high selectivity for glioma (U251) and ovarian (OVCAR-3) cancer cell lines. Also, some β-carboline-4-thiazolidinone hybrids showed potent antiviral activity against Herpes simplex virus type-1. The N-(2-substituted-aryl-4-thiazolidinone)-carboxamide moiety in 18, 19 and 22 confer a potent anti-HSV-1 activity for these derivatives, which presented EC50values of 0.80, 2.15 and 2.02 μM, respectively. The assay results showed that the nature of 4-thiazolidinone moiety and of the substituent attached at the 3- and 1- position of β-carboline nucleus influenced the antitumor and antiviral activities.
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Doi:10.1021/jp204440s
(2011)Doi:10.1016/j.dyepig.2011.07.023
(2012)Doi:10.1002/ejoc.201300345
(2013)Doi:10.1134/S1070428013030147
(2013)Doi:10.1021/om200898t
(2012)Doi:10.1039/c1ce05718a
(2011)