51369-22-3Relevant articles and documents
The synthesis, biological evaluation and structure-activity relationship of 2-phenylaminomethylene-cyclohexane-1,3-diones as specific anti-tuberculosis agents
Rather, Muzafar Ahmad,Lone, Ali Mohd,Teli, Bisma,Bhat, Zubair Shanib,Singh, Paramjeet,Maqbool, Mubashir,Shairgojray, Bashir Ahmad,Dar, Mohd Jamal,Amin, Shajrul,Yousuf, Syed Khalid,Bhat, Bilal A.,Ahmad, Zahoor
, p. 2133 - 2141 (2017)
The present study utilised whole cell based phenotypic screening of thousands of diverse small molecules against Mycobacterium tuberculosis H37Rv (M. tuberculosis) and identified the cyclohexane-1,3-dione-based structures 5 and 6 as hits. The selected hit molecules were used for further synthesis and a library of 37 compounds under four families was synthesized for lead generation. Evaluation of the library against M. tuberculosis lead to the identification of three lead antituberculosis agents (37, 39 and 41). The most potential compound, 2-(((2-hydroxyphenyl)amino)methylene)-5,5-dimethylcyclohexane-1,3-dione (39) showed an MIC of 2.5 μg mL-1, which falls in the range of MICs values found for the known antituberculosis drugs ethambutol, streptomycin and levofloxacin. Additionally, this compound proved to be non-toxic (20% inhibition at 50 μM concentration) against four human cell lines. Like first line antituberculosis drugs (isoniazid, rifampicin and pyrazinamide) this compound lacks activity against general Gram positive and Gram negative bacteria and even against M. smegmatis; thereby reflecting its highly specific antituberculosis activity.
Vibrational Spectroscopy and Conformations of 2,2-Diacylethenamines
Gomez-Sanchez, Antonio,Martin, M. de Gracia Garcia,Borrachero, Pastora,Bellanato, Juana
, p. 301 - 306 (2007/10/02)
The i.r., Raman, and 1H n.m.r. spectra of 2,2-diacetylethenamines (3) and 2-aminomethylene-5,5-dimethylcyclohexane-1,3-diones (4) show that these substances exist exclusively in the chelated enamino-diketone form, and that the conjugated system contained in them is essentially planar.The open-chain enamino-diketones (3) exist either in the solid state or in solution in the EZE-conformation (7).A similar conjugated core, having the fixed ZZE-conformation, contained in 5-aminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones (5) is most probably planar or nearly planar.The EZE- and ZZE-alignments of the enamino-diketones can be distinguished by their spectral properties, and, particularly, by their vibrational spectra.Some features of the i.r. and Raman spectra indicate vibrational coupling between the two ν(C=O) vibrations, the effect being more marked in the cyclic enamino-diketones (4) and -diesters (5) than in their open-chain analogues.On the other hand, the coupling of the ν(C=O) with the ν(C=C) and the δ(N-H) modes seems to be less efficient in these enaminodione systems than in the related simple enaninones.Further arguments are presented questioning the criteria established to ascertain the planarity of enamino-diones and of other enamines having two strong electron-acceptor groups at C-2.
