41580-72-7Relevant articles and documents
Glucosyl-1,2,3-triazoles derived from eugenol and analogues: Synthesis, anti-Candida activity, and molecular modeling studies in CYP-51
Magalh?es, Lorena Severiano de,Reis, Adriana Cotta Cardoso,Nakao, Izadora Amaral,Péret, Vinícius Augusto Campos,Reis, Rúbia Castro Fernandes Melo,Silva, Naiara Chaves,Dias, Amanda Latércia Tranches,Carvalho, Diogo Teixeira,Dias, Danielle Ferreira,Brand?o, Geraldo Célio,Braga, Saulo Fehelberg Pinto,Souza, Thiago Belarmino de
, p. 903 - 913 (2021/09/15)
This work describes the synthesis, anti-Candida, and molecular modeling studies of eighteen new glucosyl-1,2,3-triazoles derived from eugenol and correlated phenols. The new compounds were characterized by combined Fourier Transform Infrared, 1H and 13C nuclear magnetic resonance and spectroscopy of high-resolution mass spectrometry. The synthesized compounds did not show significant cytotoxicity against healthy fibroblast human cells (MCR-5) providing interesting selectivity indexes (SI) to active compounds. Considering the antifungal activity, nine compounds showed anti-Candida potential and the peracetylated triazoles 17 and 18 were the most promising ones. Eugenol derivative 17 was active against three species of Candida at 26.1–52.1?μM. This compound was four times more potent than fluconazole against Candida krusei and less toxic (SI?>?6.6) against the MCR-5 cells than fluconazole (SI?>?3.3) considering this strain. Dihydroeugenol derivative 18?showed similar activity to 17 and was four times more potent and less toxic than fluconazole against C.?krusei. The deacetylated glucosides and non-glucosylated corresponding derivatives did not show considerable antifungal action, suggesting that the acetyl groups are essential for their anti-Candida activity. Molecular docking coupled with molecular dynamics showed that 14α-lanosterol demethylase is a feasible molecular target, since 17 and 18 could bind to this enzyme once deacetylated in vivo, thereby acting as prodrugs. Also, these studies demonstrated the importance of hydrophobic substituents at the phenyl ring.
Synthesis of pterocarpans through palladium-catalyzed oxyarylation of alkoxy-2H-chromenes with o-iodophenols
Gaspar, Francisco V.,Barcellos, Julio C.F.,Cívicos, José F.,Merino, Pedro,Nájera, Carmen,Costa, Paulo R.R.
, (2020/10/22)
The oxyarylation of alkoxy-2H-chromenes (1a-e) with o-iodophenols substituted by electron-withdrawing (CHO) and electron-donating (OMe) groups is studied under two experimental conditions: a) Pd(OAc)2, Ag2CO3 in PEG-400 at 140 °C, 10 min and b) oxime-based palladacycle, DIPEA, in PEG-400 at 150 °C, 3–4 h. Pterocarpans are obtained in moderate to good chemical yields.
Electrostatic Control of Regioselectivity in Au(I)-Catalyzed Hydroarylation
Lau, Vivian M.,Pfalzgraff, William C.,Markland, Thomas E.,Kanan, Matthew W.
supporting information, p. 4035 - 4041 (2017/03/31)
Competing pathways in catalytic reactions often involve transition states with very different charge distributions, but this difference is rarely exploited to control selectivity. The proximity of a counterion to a charged catalyst in an ion paired comple
