5327-23-1Relevant academic research and scientific papers
Delineating the Role of Substituents on the Coordination Behavior of Aroylhydrazone Ligands in PdII Complexes and their Influence on Suzuki–Miyaura Coupling in Aqueous Media
Vignesh, Arumugam,Shalini, Chinnuswamy,Dharmaraj, Nallasamy,Kaminsky, Werner,Karvembu, Ramasamy
, p. 3869 - 3882 (2019/09/17)
Reactions of piperonal aroylhydrazone ligands (HL1–HL4) with [PdCl2(PPh3)2] in CH3OH and CHCl3 afforded four new Pd(II) complexes (1–4) featuring diverse coordination behaviors. These complexes 1–4 were fully characterized by elemental analyses, UV/Visible, FT-IR and 1H/13C NMR spectra. The variant coordination modes of piperonal aroylhydrazone ligands with Pd(II) ion in these complexes were unambiguously confirmed by single-crystal XRD study. Though the ligands HL1–HL4 are of similar nature, one of them (HL4) possessing an electron withdrawing nitro group as substitution in the peripheral part of the hydrazone displayed an uncommon ligation towards the palladium ion. An experimentally observed molecular architects were in turn rationalized by density functional theory (DFT) calculations as well as natural bonding analysis (NBO). All these Pd(II) complexes were evaluated for their catalytic potential towards Suzuki–Miyaura cross-coupling reaction of sterically congested arylboronic acids with (hetero)arylhalides under an open-flask conditions in aqueous media with low catalyst loading. Advantageously, the selected catalyst was active up to five cycles without significant loss in activity.
Stereoselective, solvent free, highly efficient synthesis of aldo- and keto-: N -acylhydrazones applying grindstone chemistry
Dos Santos Filho, José Maurício,Pinheiro, Savio Moita
supporting information, p. 2212 - 2224 (2017/07/24)
A mild and efficient synthesis of N-acylhydrazones has been developed, applying a simple grindstone procedure, leading to a library of 51 examples exhibiting a broad variety of structural features, 21 of them described for the first time in this paper. Th
N-(1'-naphthyl)-3,4,5-trimethoxybenzohydrazide as microtubule destabilizer: Synthesis, cytotoxicity, inhibition of cell migration and in vivo activity against acute lymphoblastic leukemia
Salum, Lívia B.,Mascarello, Alessandra,Canevarolo, Rafael R.,Altei, Wanessa F.,Laranjeira, Angelo B.A.,Neuenfeldt, Patrícia D.,Stumpf, Taisa R.,Chiaradia-Delatorre, Louise D.,Vollmer, Laura L.,Daghestani, Hikmat N.,De Souza Melo, Carolina P.,Silveira, André B.,Leal, Paulo C.,Frederico, Marisa J.S.,Do Nascimento, Leandro F.,Santos, Adair R.S.,Andricopulo, Adriano D.,Day, Billy W.,Yunes, Rosendo A.,Vogt, Andreas,Yunes, José A.,Nunes, Ricardo J.
, p. 504 - 518 (2015/05/13)
Tubulin-interacting agents, like vinca alkaloid and taxanes, play a fundamental role in cancer chemotherapy, making cellular microtubules (MT), one of the few validated anticancer targets. Cancer resistance to classical MT inhibitors has motivated the development of novel molecules with increased efficacy and lower toxicity. Aiming at designing structurally-simple inhibitors of MT assembly, we synthesized a series of thirty-one 3,4,5-trimethoxy-hydrazones and twenty-five derivatives or analogs. Docking simulations suggested that a representative N-acylhydrazone could adopt an appropriate stereochemistry inside the colchicine-binding domain of tubulin. Several of these compounds showed anti-leukemia effects in the nanomolar concentration range. Interference with MT polymerization was validated by the compounds' ability to inhibit MT assembly at the biochemical and cellular level. Selective toxicity investigations done with the most potent compound, a 3,4,5-trimethoxy-hydrazone with a 1-naphthyl group, showed remarkably selective toxicity against leukemia cells in comparison with stimulated normal lymphocytes, and no acute toxicity in vivo. Finally, this molecule was as active as vincristine in a murine model of human acute lymphoblastic leukemia at a weekly dose of 1 mg/kg.
Antibacterial activity of chalcones, hydrazones and oxadiazoles against methicillin-resistant Staphylococcus aureus
Moreira Osório, Thaís,Delle Monache, Franco,Domeneghini Chiaradia, Louise,Mascarello, Alessandra,Regina Stumpf, Taisa,Roberto Zanetti, Carlos,Bardini Silveira, Douglas,Regina Monte Barardi, Célia,De Fatima Albino Smania, Elza,Viancelli, Aline,Ariel Totaro Garcia, Lucas,Augusto Yunes, Rosendo,José Nunes, Ricardo,Smania Jr., Artur
supporting information; experimental part, p. 225 - 230 (2012/02/16)
The increase in antibiotic resistance due to multiple factors has encouraged the search for new compounds which are active against multidrug-resistant pathogens. In this context, chalcones, dihydrochalcones, hydrazones and oxadiazoles were tested against Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus (MRSA) isolates, which were obtained from clinical laboratories and were characterized as MRSA using traditional and molecular methods. Among 65 tested compounds, two chalcones, one dihydrochalcone and two hydrazones were active against MRSA. Based on the minimal inhibitory concentration and cytotoxicity, hydrazones provided a better selectivity index than chalcones. Active hydrazones are promising antibiotic-like substances and they should be the subject of further microbiological studies.
