555-60-2Relevant articles and documents
Novel heterocyclic disazo dyes containing pyrazole and phenylpyrazole. part 1: Synthesis, characterization, solvent polarity and acid-base sensitive characteristics
Demir?al?, Aykut
, (2021/02/02)
A series of diazotised aniline and aniline derivative compounds were reacted with solution of malononitrile in pyridine at 0–5 °C were obtained 1a-1m compounds. Then 4-arylazo-3,5-diamino-1H-pyrazole (2a-2m) derivatives were synthesized by coupling arylazo malononitrile compounds with hydrazine. Finally, the synthesized pyrazole derivative 2a-2m compounds were again diazotised. By reacting these diazotised compounds with 3-amino-5?hydroxy-1-phenylpyrazole, the new thirteen heterocyclic disazo dyes (3a-3m) were joined the dye literature and the dye industry. The structures of these newly synthesized compounds were characterized using elemental analysis and spectroscopic methods such as Fourier transform infrared spectroscopy-Attenuated total reflectance (FT-IR-ATR), 1H-Nuclear magnetic resonance (1H NMR) spectroscopy and mass spectroscopy. Then solvatochromic properties and solvent effect in dimethyl sulfoxide, dimethyl formamide, acetonitrile, acetic acid, methanol and chloroform were investigated. In addition, the effects of organic and inorganic acids and bases on the absorption spectra of the compounds and the substituent effect of the phenyl ring-bound groups were investigated.
Effect of new carbonyl cyanide aromatic hydrazones on biofilm inhibition against methicillin resistant: Staphylococcus aureus
Lu, Jun,Lu, Xueer,Tang, Wenjian,Xu, Yingying,Zhang, Jing,Zhang, Ziwen
, p. 17854 - 17861 (2020/06/17)
Carbonyl cyanide m-chlorophenylhydrazone (CCCP), as a protonophore, in combination with antibiotics exhibited potentiating antibacterial activity. To improve CCCP's potency and toxicity, a series of aromatic hydrazones were synthesized and their antimicrobial activity was evaluated; amongst them, compounds 2e and 2j with a strong para-electron-withdrawing substituent (-NO2 and -CF3) at the phenyl ring had the lowest MICs against both S. aureus and methicillin resistant Staphylococcus aureus (1.56 and 1.56 μM, respectively). Some compounds in combination with antibiotics exhibited potentiate Gram-positive antibacterial activity; compound 2e was found to display unaided or synergistic efficacy against MRSA. In particular, when compound 2e is combined with ofloxacin, it has a good synergistic effect against MRSA. Moreover, electron microscopy revealed that compound 2e inhibits biofilm formation and effectively eradicates preformed biofilm. MTT assay showed that compound 2e displays as low toxicity as CCCP. Overall, our data showed that the aromatic hydrazone is a promising scaffold for anti-staphylococcal drug development.
Discovery, SAR study and ADME properties of methyl 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate as an HIV-1 replication inhibitor
Alvarez, Karine,Busca, Patricia,Calvez, Vincent,Delelis, Olivier,Fichez, Jeanne,Gizzi, Patrick,Gravier-Pelletier, Christine,Le Corre, Laurent,Prestat, Guillaume,Sayon, Sophie,Soulie, Cathia,Marcelin, Anne-Geneviève,Priet, Stéphane
, p. 577 - 582 (2020/06/04)
Inspired by the antiviral activity of known pyrazole-based HIV inhibitors, we screened our in-house library of pyrazole-based compounds to evaluate theirin celluloactivity against HIV-1 replication. Two hits with very similar structures appeared from single and multiple-round infection assays to be non-toxic and active in a dose-dependent manner. Chemical expansion of their series allowed an in-depth and consistent structure-activity-relationship study (SAR) to be built. Further ADME evaluation led to the selection of 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate with an advantageous pharmacokinetic profile. Finally, examination of its mode of action revealed that this compound does not belong to the three main classes of anti-HIV drugs, a feature of prime interest in the context of viral resistance.
