Síntese e avaliação da atividade fitotóxica de derivados da α-Santonina

Alvarenga, Elson S.; Barbosa, Luiz C. A.; Saliba, William Argolo; Arantes, Francisco F. P.; Demuner, Antônio J.; Silva, Antônio Augusto Moura da

doi:10.1590/s0100-40422009000200025

Cited by 17 publications

(24 citation statements)

References 20 publications

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“…The presence of these signals along other signals assisted in confirming the formation of the compounds 11e14. The a-orientation of the aliphatic chain in C-11 was assigned from the value of J 7,11 (12.0 Hz) similar to those found for others eudesmanolides and guaianolides with H-11b [40,41]. The proposed stereochemistry was confirmed by NOEDIFF experiment analysis, where it was detected NOE between the irradiated hydrogen H6-b and the hydrogen H11.…”

Section: Synthesissupporting

confidence: 69%

Synthesis of novel α-santonin derivatives as potential cytotoxic agents

Arantes

Barbosa

Maltha

et al. 2010

European Journal of Medicinal Chemistry

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Ten novel α-santonin derivatives have been synthesized as cytotoxic agents. The in vitro antitumor activity of these compounds has been evaluated against cancer cells lines. Structure-activity relationships indicate that α-methylene-γ-lactone and endoperoxide functionalities play important roles in conferring cytotoxicity. The compounds 2-4, possessing the α-methylene-γ-lactone group showed IC50 values between 5.70 and 16.40 μM. Mixture of isomers 5 and 6, with the α-methylene-γ-lactone and endoperoxide functionalities, displayed the greatest activity, with IC50 values between 1.45 and 4.35 μM. The biological assays conducted with normal cells revealed that the compounds 2, 5 and 6 are selective against cancer cells lines tested. Bioactive lactones described herein and in our previous report did not cause disruption of the cell membrane in mouse erythrocytes.

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Section: Synthesissupporting

confidence: 69%

Synthesis of novel α-santonin derivatives as potential cytotoxic agents

Arantes

Barbosa

Maltha

et al. 2010

European Journal of Medicinal Chemistry

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“…This property can determine the compound bioavailability in the cell and the efficiency of the transport of compounds in the phloem of plants . The viability of this methodology is observed in the literature …”

Section: Introductionmentioning

confidence: 99%

Herbicidal activity of isobenzofuranones and in silico identification of their enzyme target

Teixeira

Alvarenga

Lopes

et al. 2019

Pest Management Science

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BACKGROUND Given the weed resistance to various herbicides with different mechanisms of action, the search for new compounds that are more effective and exhibit low levels of impact to other species in nature has been imperative in the field of the agriculture. For this purpose, 16 phthalides, and furan‐2(5H)‐one were synthetized and evaluated for their effectiveness as herbicides in seeds of Sorghum bicolor (sorghum), Cucumis sativus (cucumber), and Allium cepa (onion). Furthermore, a preliminary in silico study was carried out to identify the enzyme target of the most active compounds. RESULTS In the assays with S. bicolor, the mixture rac‐(3aR,4R,5S,6S,7S,7aS)‐5,6‐dibromohexahydro‐4,7‐methanoisobenzofuran‐1(3H)‐one + rac‐(3aR,4R,5R,6R,7S,7aS)‐5,6‐dibromohexahydro‐4,7‐methanoisobenzofuran‐1(3H)‐one (15a + 15b) showed comparable inhibitory activity to (S)‐metolachlor, which was used as control herbicide at concentrations ranging from 50 μm to 1000 μm. The developments of the seeds evaluated were altered by all 17 compounds, either stimulating or inhibiting. The best results were presented by compounds 15a, and 15b, either in their pure form or as a mixture. CONCLUSION The results presented by 15a, and 15b were superior to the activity of the commercial herbicide (S)‐metolachlor in the assays with C. sativus, and A. cepa. The in silico study provides strong evidence that the most active compounds bind to strigolactones esterases D14 through the same binding site of (5R)‐5‐hydroxy‐3‐methylfuran‐2(5H)‐one (H3M), which is one of the strigolactones (SLs) cleavage products. © 2019 Society of Chemical Industry

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“…The use of phytotoxic natural products as models for the development of synthetic analogues with herbicidal activity has been regarded as a promising strategy in the search for novel herbicides [5][6][7]. Such strategy has been extensively explored by our research group [8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%