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
Half-wave potentials and in vitro cytotoxic evaluation of 3-acylated 2,5-bis(phenylamino)-1,4-benzoquinones on cancer cells
Benites, Julio,Valderrama, Jaime A.,Ramos, Maryan,Valenzuela, Maudy,Guerrero-Castilla, Angélica,Muccioli, Giulio G.,Calderon, Pedro Buc
, (2019/05/24)
A broad range of 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones were synthesized and their voltammetric values, as well as in vitro cancer cell cytotoxicities, were assessed. The members of this series were prepared from acylbenzoquinones and phenylamines, in moderate to good yields (47-74%), through a procedure involving a sequence of two in situ regioselective oxidative amination reactions. The cyclic voltammograms of the aminoquinones exhibit two one-electron reduction waves to the corresponding radical-anion and dianion, and two quasi-reversible oxidation peaks. The first and second half-wave potential values (E1/2) of the members of the series were sensitive to the push-pull electronic effects of the substituents around the benzoquinone nucleus. The in vitro cytotoxic activities of the 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones against human cancer cells (bladder and prostate) and non-tumor human embryonic kidney cells were measured using the MTT colorimetric method. The substitution of both aniline groups, by either methoxy (electron donating effect) or fluorine (electron withdrawal effect), decreased the cytotoxicity in the aminoquinones. Among the members of the unsubstituted phenylamino series, two of the 18 compounds showed interesting anti-cancer activities. A preliminary assay, looking for changes in the expression of selected genes, was performed. In this context, the two compounds increased TNF gene expression, suggesting an association with an inflammatory-like response.
