27210-58-8Relevant academic research and scientific papers
Design and synthesis of some acridine-piperazine hybrids for the improvement of cognitive dysfunction
Sharma, Anuradha,Piplani, Poonam
, p. 926 - 935 (2017)
A novel series of hybrid molecules (5a–5m) was designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against cognitive dysfunction. Heterocyclic moieties acridine and piperazine were conjugated with suitable linkers in a single scaffold, and the structures of the target compounds were confirmed by IR, 1H NMR, 13C NMR, and LC-MS analysis. The pharmacological activity of synthesized compounds was evaluated using behavioral models of amnesia viz. step-down passive avoidance and elevated plus maze at a dose 0.5?mg/kg as compared to standard rivastigmine. In vitro acetylcholinesterase (AChE) inhibition studies using brain homogenate of mice as the enzyme source revealed that most of the compounds exhibited a significant ability to inhibit the enzyme cholinesterase with compound 5c being the most potent (IC50 0.33?μm). Biochemical estimation of oxidative stress markers viz. plasma nitrite, thiobarbituric acid reactive substances, catalase, superoxide dismutase, and glutathione has been carried out using the respective assays to see the effect of the synthesized compounds on the scopolamine-induced oxidative damage. The molecular docking studies indicated the binding mode of the compounds to the catalytic site, peripheral site, and mid-gorge of AChE simultaneously. The calculated absorption, distribution, metabolism and excretion properties ensured the drug-likeness of the target compounds. The synthesized compounds were found to be potential cognitive enhancers, which were able to interfere with the scopolamine-induced oxidative stress also.
Design, synthesis, biological evaluation, molecular docking and QSAR studies of 2,4-dimethylacridones as anticancer agents
Murahari, Manikanta,Kharkar, Prashant S.,Lonikar, Nitin,Mayur
, p. 154 - 170 (2017)
Drug resistance in cancer is an unmet medical challenge and a major drawback for the failure of many chemotherapeutic drugs. Search for targeted, effective drug with minimum toxicity is an urgent need. Acridone which is an alkaloid derivative has been att
Redox-neutral decarboxylative photocyclization of anthranilic acids
Huang, Huawen,Deng, Kun,Deng, Guo-Jun
supporting information, p. 8243 - 8247 (2020/12/29)
A mild metal-, catalyst-, and oxidant-free photoredox neutral system has been found to efficiently enable intramolecular decarboxylative cyclization of anthranilic acids. This facile protocol provides an alternative method for the synthesis of carbazoles. Mechanistic studies reveal a key photoinduced 6π-electrocyclization process and formic acid was released as the sole byproduct.
Structure-activity relationships in a series of anti-inflammatory N-arylanthranilic acids
Kaltenbronn,Scherrer,Short,Jones,Beatty,Saka,Winder,Wax,Williamson
, p. 621 - 627 (2007/10/02)
A large series of N-arylanthranilic acids has been prepared. Many of these compounds show high anti-inflammatory activity as measured by the anti-UV-erythema test. From this series have come the clinically useful nonsteroidal anti-inflammatory agents, flufenamic acid (Arlef), mefenamic acid (Ponstel), and the latest and most potent agent, N-(2,6-dichloro-m-tolyl)anthranilic acid (meclofenamic acid, Meclomen = the sodium salt). The structure-activity relationships of this series is discussed and a graphical representation is presented which allows the prediction of activity of new agents.
An In-depth Study of the Azidobenzophenone-Anthranil-Acridone Transformation
Hawkins, David G.,Meth-Cohn, Otto
, p. 2077 - 2087 (2007/10/02)
The title transformation, particularly the conversion of anthranils into acridones, is shown to be critically sensitive to temperature, solvent, substituent, and metal catalysts.Thus the conversion of 3-(p-tolyl)anthranil into an acridone gives a ratio of 2-and 3-methyl derivatives varying from 0.6:1 to 4.7:1 with changing temperature and solvent.In other similar thermolyses, solvents (e.g. 1,2,4-trichlorobenzene) were incorporated into the product and traces of metals and their derivatives had a dramatic effect on the rate and course of the reaction.The most effective catalysts were iron powder and aluminium acetylacetonate. 3-(2,6-Disubstituted phenyl)anthranils gave acridones in which the substituents were either lost or rearranged onto N or C, the last cases involving sequential -sigmatropic shifts. 3-Thienylanthranils gave related thienoquinolones on thermolysis; again the reaction were very sensitive to catalysis.Blocked thienylanthranils also gave rearrangement products, but the non-aromatic intermediates could be isolated.
COMPOSES SULFURES HETEROCYCLIQUES. XCVI. REACTION DE L'HYDRAZINE SUR LES DIHYDRO-1,2 BENZOTHIAZINE-3,1 THIONES-4
Legrand, Louis,Lozac'H, Noel
, p. 139 - 143 (2007/10/02)
1-Alkyl-1,2-dihydro-3,1-benzothiazine-4-thiones 1, when reacting with hydrazine, give with a good yield a 1-alkyl-3-amino-2,3-dihydro-1H-quinazoline-4-thione-2, often together with a derivative of 1,3,4-thiadiazole-3. With 1-aryl-1,2-dihydro-3,1-benzothiazine-4-thiones, the main product of the reaction with hydrazine appears to be a 1-aryl-4-hydrazono-1,4-dihydro-2H-3,1-benzothiazine 4, sometimes with some amount of 3.On the contrary, when reacting with hydrazine, 1-alkyl (or 1-aryl)-1,2-dihydro-3,1-benzothiazin-4-ones lead to a 2-alkylamino (or arylamino)-benzohydrazide 5. By thermolysis 4 isomerizes into 2 which is accompanied by derivatives (3 and 7) of 1,3,4-thiadiazole.The structures of compounds 2, 4 and 7 have been studied by NMR and UV spectrometry.
