1125-55-9Relevant articles and documents
Synthesis of 1-(Indol-2-yl)-phenoxazine hybrids from quinacetophenone precursors and their biological evaluation as DNA intercalating agents
Dixit, Apoorva,Godugu, Chandraiah,Kotla, Naveen,Lakshmi Uppu, Jaya,Nunewar, Saiprasad N.,Pooladanda, Venkatesh,Tangellamudi, Neelima D.
, (2020)
An operationally simple reaction between quinacetophenone and aniline derivatives in the presence of triethylamine at room temperature afforded 1-(indol-2-yl)-phenoxazine hybrids in good yields. This unique transformation proceeds via sequential aza-Micha
Quinacetophenone: A simple precursor for synthesis of phenoxazines
Nunewar, Saiprasad N.,Muthyala, Bhavana B.,Dastari, Sowmya,Tangellamudi, Neelima D.
, p. 14952 - 14960 (2019)
Quinacetophenone is a versatile and easy accessible building block for synthesis of various biologically active heterocyclic compounds. The inherent chemical reactivity of quinacetophenone has been hitherto utilized to construct various privileged organic molecules such as chalcones, chromones, flavonoids, coumarins and azoles etc. Herein we present an operationally simple method of synthesis of phenoxazines from quinacetophenone and anilines that exploits the inherent chemical reactivity of quinacetophenone. ESI-MS was used as a tool to establish the most plausible reaction mechanism.
Silica-gel-supported ceric ammonium nitrate (CAN): A simple and efficient solid-supported reagent for oxidation of oxygenated aromatic compounds to quinones
Ali, Mohammed Hashmat,Niedbalski, Melinda,Bohnert, Gary,Bryant, Daniel
, p. 1751 - 1759 (2006)
A silica-gel-supported heterogeneous ceric ammonium nitrate (CAN) reagent has been developed for oxidizing oxygenated aromatics to quinones in nonaqueous media. The advantages of this procedure include excellent yields, mild reaction conditions, nonaqueous media, short reaction times, and easy product isolation. Copyright Taylor & Francis Group, LLC.
The synthesis of some fused pyrazolo-1,4-naphthoquinones
Molinari, Aurora,Oliva, Alfonso,Arismendi, Marlene,Imbarack, Elizabeth,Gálvez, Cristian,Maldonado, Javier,Feliciano, Arturo San
, p. 620 - 622 (2015)
New fused pyrazolo-1,4-naphthoquinones were prepared from the reaction of hydrazines with 6-(4-methyl-3-pentenyl)-1,4-naphthoquinone. The reaction was extended to hydroxylamine to afford the corresponding isoxazolo-1,4-napthoquinone compound.
Cytotoxic-antineoplastic activity of acetyl derivatives of prenylnaphthohydroquinone
Molinari, Aurora,Oliva, Alfonso,Del Corral, Jose Ma. Miguel,Castro, Ma. Angeles,Araya, Claudia,Garcia-Gravalos, Ma. Dolores,San Feliciano, Arturo
, p. 651 - 656 (2004)
Several acetyl derivatives of prenylnaphthohydroquinone have been synthetised and evaluated for their cytotoxicity against A-549 human lung carcinoma and H-116 human colon carcinoma neoplastic cells. The IC50 values against A-549 are compared w
Assessing parameter suitability for the strength evaluation of intramolecular resonance assisted hydrogen bonding in O-carbonyl hydroquinones
Martínez-Cifuentes, Maximiliano,Monroy-Cárdenas, Matías,Millas-Vargas, Juan Pablo,Weiss-López, Boris E.,Araya-Maturana, Ramiro
, (2019/02/01)
Intramolecular hydrogen bond (IMHB) interactions have attracted considerable attention due to their central role in molecular structure, chemical reactivity, and interactions of biologically active molecules. Precise correlations of the strength of IMHB’s with experimental parameters are a key goal in order to model compounds for drug discovery. In this work, we carry out an experimental (NMR) and theoretical (DFT) study of the IMHB in a series of structurally similar o-carbonyl hydroquinones. Geometrical parameters, as well as Natural Bond Orbital (NBO) and Quantum Theory of Atoms in Molecules (QTAIM) parameters for IMHB were compared with experimental NMR data. Three DFT functionals were employed to calculated theoretical parameters: B3LYP, M06-2X, and ωB97XD. O . . . H distance is the most suitable geometrical parameter to distinguish among similar IMHBs. Second order stabilization energies ?Eij(2) from NBO analysis and hydrogen bond energy (EHB) obtained from QTAIM analysis also properly distinguishes the order in strength of the studied IMHB. ?Eij(2) from NBO give values for the IMHB below 30 kcal/mol, while EHB from QTAIM analysis give values above 30 kcal/mol. In all cases, the calculated parameters using ωB97XD give the best correlations with experimental1H-NMR chemical shifts for the IMHB, with R2 values around 0.89. Although the results show that these parameters correctly reflect the strength of the IMHB, when the weakest one is removed from the analysis, arguing experimental considerations, correlations improve significantly to values around 0.95 for R2