461688-29-9Relevant academic research and scientific papers
Synthesis, biological activity, and docking study of novel isatin coupled thiazolidin-4-one derivatives as anticonvulsants
Nikalje, Anna P.,Ansari, Altamash,Bari, Sanjay,Ugale, Vinod
, p. 433 - 445 (2015)
A series of 2-(substituted-phenyl)-3-(2-oxoindolin-3-ylidene)amino)-thiazolidin-4-one derivatives were designed and synthesized under microwave irradiation, using an eco-friendly, efficient, microwave-assisted synthetic protocol that involves cyclocondensation of 3-substituted benzylidine-hydrazono-indolin-2-one 3a-j with thioglycolic acid in dimethyl formamide (DMF) as solvent and anhydrous zinc chloride as a catalyst, keeping in view the structural requirement of the pharmacophore. The intermediate compounds 3a-j were obtained by condensation of the hydrazone of indoline-2,3-dione with aromatic aldehydes. The synthesized derivatives were evaluated for CNS depressant activity and anticonvulsant activity in mice using the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (sc-PTZ) induced seizure tests. All the derivatives showed good CNS depressant activity and showed protection in the MES test, indicative of their ability to inhibit the seizure spread. A histopathological study was performed to evaluate liver toxicity caused by the synthesized compounds. The compounds were nontoxic. A computational study was performed, in which log P values were calculated experimentally. Virtual screening was performed by molecular docking of the designed compounds into the ATP binding sites of the NMDA and AMPA receptors, to predict if these compounds have analogous binding modes.
New hydrazonoindolin-2-ones: Synthesis, exploration of the possible anti-proliferative mechanism of action and encapsulation into PLGA microspheres
Attia, Mohamed I.,Eldehna, Wagdy M.,Afifi, Samar A.,Keeton, Adam B.,Piazza, Gary A.,Abdel-Aziz, Hatem A.
, (2017/07/28)
The synthesis and molecular characterization of new isatin-based hydrazonoindolin-2-ones 4a-o and 7a-e are reported. The in vitro anti-proliferative potential of the synthesized compounds 4a-o and 7a-e was examined against HT-29 (colon), ZR-75 (breast) and A549 (lung) human cancer cell lines. Compounds 7b, 7d and 7e were the most active congeners against the tested human cancer cell lines with average IC50 values of 4.77, 3.39 and 2.37 μM, respectively, as compared with the reference isatin-based drug, sunitinib, which exhibited an average IC50 value of 8.11 μM. Compound 7e was selected for further pharmacological evaluation in order to gain insight into its possible mechanism of action. It increased caspase 3/7 activity by 2.4- and 1.85-fold between 4 and 8 h of treatment, respectively, at 10 μM and it caused a decrease in the percentage of cells in the G1 phase of the cell cycle with a corresponding increase in the S-phase. In addition, compound 7e increased phosphorylated tyrosine (p-Tyr) levels nearly two-fold with an apparent IC50 value of 3.8 μM. The 7e-loaded PLGA microspheres were prepared using a modified emulsion-solvent diffusion method. The average encapsulation efficiency of the 7e-loaded PLGA microspheres was 85% ± 1.3. While, the in vitro release profile of the 7e-loaded microspheres was characterized by slow and continuous release of compound 7e during 21 days and the release curve was fitted to zero order kinetics. Incorporation of 7e into PLGA microspheres improved its in vitro anti-proliferative activity toward the human cancer cell line A549 after 120 h incubation period with an IC50 value less than 0.8 μM.
Synthesis of some new mixed azines, Schiff and Mannich bases of pharmaceutical interest related to isatin
Afsah, Elsayed M.,Elmorsy, Saad S.,Abdelmageed, Soha M.,Zaki, Zaki E.
, p. 393 - 402 (2015/06/17)
The mixed azines 3a-h and 4 were obtained by treating 3-hydrazonoindolin-2-one (2) with the appropriate aldehyde or dialdehyde. Treatment of 3b or 3c with formaldehyde or glutaric dialdehyde and the appropriate amine afforded the azine Mannich bases 5-7. The condensation of isatin or its N-Mannich base 8 with 1-aminopiperidine, 4-aminomorpholine and 1,4-diaminopiperazine gave 10a- d, 12 and 13. The Mannich bases 14 and 15 were obtained from 10a and 10b. Treatment of 2 with succinic, phthalic and quinolinic anhydride and pyromellitic dianhydride afforded compounds 16, 17a, 17b and 18, respectively. The synthesis of isatin Schiff bases incorporating a benzoylpiperidine, benzoylmorpholine and 1,4-dibezoylpiperazine moiety and their N-Mannich bases was investigated.
Synthesis, characterization and in vitro antimicrobial evaluation of new compounds incorporating oxindole nucleus
Kandile, Nadia G.,Zaky, Howida T.,Mohamed, Mansoura I.,Ismaeel, Hind M.,Ahmed, Nashwa A.
experimental part, p. 599 - 608 (2012/09/08)
New compounds incorporating with the oxindole nucleus were synthesized via the reaction of substituted isatins [5-methyl-, 5-chloro- and 1-hydroxymethyl isatins] with different nucleophiles. The structures of the newly compounds were elucidated on the bas
