Synthesis and antitumor activity of novel 1-substituted phenyl 3-(2-oxo-1,3,4-oxadiazol-5-yl) β-carbolines and their Mannich bases

Savariz, Franciele Cristina; Foglio, Mary Ann; Ruiz, Ana Lúcia T. G.; Costa, Willian Ferreira da; Silva, Marina de Magalhães; Santos, Josué Carinhanha Caldas; Figueiredo, Isis M.; Meyer, Edenilson; Carvalho, João Ernesto de; Sarragiotto, María Helena

doi:10.1016/j.bmc.2014.10.031

Cited by 35 publications

(15 citation statements)

References 30 publications

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“…6 d), using up to 30 times excess of the ligands over the initial amount of ethidium bromide. Thus, suggesting that the evaluated compounds interact preferentially by intercalation [56] , confirming the previous results. Finally, the confirmation of the binding mode by intercalation corroborates with works of the literature that evaluated the interaction of compounds containing the piperidine nucleus with DNA [44] , [45] , [46] , [47] .…”

Section: Resultssupporting

confidence: 90%

Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity

Das

Silva

et al. 2018

Journal of Advanced Research

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Section: Resultssupporting

confidence: 90%

Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity

Das

Silva

et al. 2018

Journal of Advanced Research

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“…All newly synthesized compounds were purified by crystallization and their structures were confirmed on the basis of 1 H NMR, 13 C NMR and HRMS data, which are given in Section 4 . Compounds 3 , 9 , 10 , 13 and 25 were characterized by comparison with NMR data previously reported [ 27 , 32 ]. Compounds 24 – 29 were characterized by the presence of an additional signal at δ H 12.69–12.60 or 7.25–7.29, corresponding to the 3′-NH or 2′-NH 2 on the 1,3,4-oxadiazole scaffold, respectively.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Bioactivity Evaluation of Novel β-carboline 1,3,4-oxadiazole Derivatives

Zhang

Jiang

et al. 2017

Molecules

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A series of novel β-carboline 1,3,4-oxadiazole derivatives were designed and synthesized, and the in vitro cytotoxic activity against Sf9 cells and growth inhibitory activity against Spodoptera litura were evaluated. Bioassay results showed that most of these compounds exhibited excellent in vitro cytotoxic activity. Especially, compound 37 displayed the best efficacy in vitro (IC50 = 3.93 μM), and was five-fold more potent than camptothecin (CPT) (IC50 = 18.95 μM). Moreover, compounds 5 and 37 could induce cell apoptosis and cell cycle arrest and stimulate Sf-caspase-1 activation in Sf9 cells. In vivo bioassay also demonstrated that compounds 5 and 37 could significantly inhibit larvae growth of S. litura with decreasing the weight of larvae and pupae. Based on these bioassay results, compounds 5 and 37 emerged as lead compounds for the development of potential insect growth inhibitions.

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“…Lower KSV values recorded in presence of ctDNA compared to free molecule confirmed the ability of 48 in ctDNA interaction. Furthermore, increasing concentrations of 48 induced reduction of the emission intensity of the EB-ctDNA complex until 62% (at 20 µM 48), evidencing that the two ligands (48 and EB) interact with ctDNA in the same mode through intercalation [80].…”

Section: Nucleic Acid Structures As Oxadiazole Targetsmentioning

confidence: 91%

“…In a previous work, the authors improved the antitumor activity of β-carboline by introducing a thioxo-1,3,4-oxadiazolyl unit at C-3 position of carboline [79]. In an effort to achieve even better effects, they decided to replace the thioxo group with a 2-oxo derivative [80]. Antiproliferative activity was tested towards different cancer cell lines and the best outcome was achieved with (Figure 9), characterized by the presence of N,N-dimethylamino group on carboline.…”

Section: Nucleic Acid Structures As Oxadiazole Targetsmentioning

confidence: 99%

Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds

Benassi

Doria

Pirota

2020

Preprint

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Nowadays, an increasing number of heterocyclic-based drugs found application in medicinal chemistry and, in particular, as anticancer agents. In this context, oxadiazoles, five-membered aromatic rings, emerged for their interesting biological properties. Modification of oxadiazole scaffolds represents a valid strategy to increase their anticancer activity, especially on 1,2,4 and 1,3,4 regioisomers. In the last years, an increasing number of oxadiazole derivatives, with remarkable cytotoxicity for several tumor lines, were identified. Structural modifications, that ensure higher cytotoxicity towards malignant cells, represent a solid starting point in the development of novel oxadiazoles-based drugs. To increase the specificity of this strategy, outstanding oxadiazole scaffolds have been designed to selectively interact with biological targets, including enzymes, globular proteins and nucleic acids, showing more promising antitumor effects. In the present work, we aim to provide a comprehensive overview of the anticancer activity of these heterocycles, describing their effect on different targets and highlighting how their structural versatility has been exploited to modulate their biological properties.

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Synthesis and antitumor activity of novel 1-substituted phenyl 3-(2-oxo-1,3,4-oxadiazol-5-yl) β-carbolines and their Mannich bases

Cited by 35 publications

References 30 publications

Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity

Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity

Design, Synthesis and Bioactivity Evaluation of Novel β-carboline 1,3,4-oxadiazole Derivatives

Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds

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