70565-01-4

Upstream product

• 2365-44-8 3-hydrazonoindolin-2-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 2143-99-9 1,2-bis(4-nitrobenzylidene)hydrazine 
• 2299-73-2 N,N-bis(4-methoxybenzylidene)hydrazine 
• 3510-48-3 4-chlorobenzaldehyde azine 
• 588-68-1 1,2-di(benzylidene)hydrazine 
• 21540-02-3 3,3'-(hydrazine-1,2-diylidene)bis(indolin-2-one) 
• 70565-02-5 3-((4-chlorobenzylidene)hydrazono)indolin-2-one 
• 70565-03-6 4-nitrobenzaldehyde-N-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)hydrazone 

Relevant academic research and scientific papers

Novel thiomorpholine tethered isatin hydrazones as potential inhibitors of resistant Mycobacterium tuberculosis

Novel chemotherapeutic agents against multidrug resistant-tuberculosis (MDR-TB) are urgently needed at this juncture to save the life of TB-infected patients. In this work, we have synthesized and characterized novel isatin hydrazones 4(a-o) and their thi

New hydrazonoindolin-2-ones: Synthesis, exploration of the possible anti-proliferative mechanism of action and encapsulation into PLGA microspheres

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, biological activity, and docking study of novel isatin coupled thiazolidin-4-one derivatives as anticonvulsants

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.

Synthesis of some new mixed azines, Schiff and Mannich bases of pharmaceutical interest related to isatin

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.

Novel coordination complexes of the trivalent ruthenium, rhodium and iridium with hydrazones derived from isatin hydrazide and various aldehydes with spectral and biological characterization

A series of several new ruthenium(III), rhodium(III) and iridium(III) complexes with hydrazones of general formula [M(LH)3]Cl3 were synthesized in order to meet requirements essential for biological properties. Hydrazones were formed by isatin hydrazide and various aldehydes namely anisaldehyde, benzaldehyde, o-chlorobenzaldehyde, p-chlorobenzaldehyde and p-fluorobenzaldehyde. Physicochemical characterization of compounds has been carried out by elemental analyses, spectroscopic (IR, electronic, 1H NMR), thermogravimetric and magnetic studies. These complexes show higher conductance values, supporting their electrolytic nature. All the studies revealed octahedral nature of the complexes with nitrogen and oxygen of azomethine and carbonyl group as binding sites and exhibited monomeric nature of the complexes. Rhodium(III) and iridium(III) complexes were found diamagnetic and show intense absorptions while ruthenium(III) complexes show paramagnetic behaviour. In addition, antifungal and antibacterial studies have been carried out in vitro for investigated compounds against fungus A. niger and F. oxysporium and bacteria E. coli and S. aureus. Most of the metal chelates show higher biocidal activity for the above microorganisms than that of the free ligand.