256427-07-3Relevant articles and documents
Discovery of a new class of sortase a transpeptidase inhibitors to tackle gram-positive pathogens: 2-(2-phenylhydrazinylidene)alkanoic acids and related derivatives
Maggio, Benedetta,Raffa, Demetrio,Raimondi, Maria Valeria,Cascioferro, Stella,Plescia, Fabiana,Schillaci, Domenico,Cusimano, Maria Grazia,Leonchiks, Ainars,Zhulenkovs, Dmitrijs,Basile, Livia,Daidone, Giuseppe
, (2016/04/20)
A FRET-based random screening assay was used to generate hit compounds as sortase A inhibitors that allowed us to identify ethyl 3-oxo-2-(2-phenylhydrazinylidene)butanoate as an example of a new class of sortase A inhibitors. Other analogues were generated by changing the ethoxycarbonyl function for a carboxy, cyano or amide group, or introducing substituents in the phenyl ring of the ester and acid derivatives. The most active derivative found was 3-oxo-2-(2-(3,4dichlorophenyl)hydrazinylidene)butanoic acid (2b), showing an IC50 value of 50 μM. For a preliminary assessment of their antivirulence properties the new derivatives were tested for their antibiofilm activity. The most active compound resulted 2a, which showed inhibition of about 60% against S. aureus ATCC 29213, S. aureus ATCC 25923, S. aureus ATCC 6538 and S. epidermidis RP62A at a screening concentration of 100 μM.
Synthesis and tautomeric structure of 3,7-bis(arylazo)-2,6-dimethyl- 1Himidazo 1,2-b]pyrazoles
Shawali, Ahmad Sami,Abdallah, Magda A,Shehat, Mohamed R,Kandil, Mohamed
, p. 127 - 130 (2013/07/05)
Three series of 3,7-bis(arylazo)-2,6-dimethyl-1H-imidazo[1,2-b]pyrazoles were prepared starting from N-aryl-2-oxopropanehydrazonoyl chlorides. The acid dissociation constants pKa were determined and correlated with the Hammett equation. The results of suc
1,2,5,6-Tetrazocines from nitrile imines and tert-Butyl isocyanide
Moderhack, Dietrich,Daoud, Ali,Ernst, Ludger,Jones, Peter G.
, p. 707 - 710 (2007/10/03)
tert-Butyl isocyanide (2) reacts with acceptor-substituted nitrile imines to give derivatives of tetrahydro-1,2,5,6-tetrazocines 3 along with substituted 5-hydrazonoyl-1,2,4-triazoles 4. Replacement of 2 with aryl or sec-alkyl isocyanides leads to substituted α-hydrazonoamides (6B) rather than to analogues of 3; removal of the acceptor group in 1 is likewise detrimental. - The structure of 3 has been established by means of an X-ray diffraction analysis of 3d. Wiley-VCH Verlag GmbH, 2000.
The effect of ortho and para substituents on the formation of the E and Z isomers of the arylhydrazones obtained from diazonium coupling with methyl 3-aminocrotonate and 3-aminocrotononitrile
Jollimore, Jason V.,Vacheresse, Marc,Vaughan, Keith,Hooper, Donald L.
, p. 254 - 262 (2007/10/03)
Reaction of arene diazonium salts with 3-aminocrotononitrile or methyl 3-aminocrotonate affords the 2-arylhydrazono-3-oxobutanenitrile (1 or 3 and 3′) or the methyl 2-arylhydrazono-3-oxobutanoate (2 and 2′ or 4 and 4′). A series of these hydrazones has been prepared with a range of electron-withdrawing and -donating substituents in the ortho or para position of the aryl moiety. The hydrazones have been characterized by spectroscopic methods, with emphasis on the 1 H NMR spectra, which have been used to determine the configuration of the hydrazones as E or Z or a mixture of the two. The para-substituted hydrazononitriles (1) are formed as a single species, namely the Z isomer, whereas the ortho isomers are formed as a mixture of E and Z configurations (3 and 3′). The hydrazonobutanoates (2 and 2′ or 4 and 4′) are formed as E/Z mixtures regardless of the position of the substituent in the aryl moiety. Complete assignments of all signals in the 1 H NMR spectra have been made on the basis of the ability of the various substituents to participate in intramolecular hydrogen bonding and a mechanism is proposed to account for the variations in the proportions of E and Z isomers and the effect of the nature of the substituent on this ratio. 13C NMR spectra of selected hydrazones have been recorded as an aid to structure assignment.
