21540-02-3Relevant academic research and scientific papers
Hydrolysis and hydrazinolysis of isatin-based ald-and ketazines
Ibrahim, Hany S.,Abdelhadi, Soha R.,Abdel-Aziz, Hatem A.
, (2015)
The hydrolysis of isatin aldazine 4a-d afforded the unexpected 3,3'-(hydrazine-1,2-diylidene)bis(indolin-2-one) (5) and 1,2-di(arylidene)hydrazines 6a-d through dual hydrolysis of 4a-d. A mechanism to explain the formation of 5 and 6a-d was proposed. In addition, the hydrazinolysis of 4a-d yielded 3-hydrazonoindolin-2-one (2) and 1,2-di(arylidene)hydrazines 6a-d instead of hydrazones 17a-d, while hydrazinolysis of isatin ketazine 5 gave the expected 3-hydrazonoindolin-2-one (2). These results indicated the ability of the title compounds for unusual hydrolysis and hydrazinolysis reactions.
Pharmacophore modeling and 3D-QSAR study of indole and isatin derivatives as antiamyloidogenic agents targeting Alzheimer’s disease
Purgatorio, Rosa,Gambacorta, Nicola,Catto, Marco,de Candia, Modesto,Pisani, Leonardo,Espargaró, Alba,Sabaté, Raimon,Cellamare, Saverio,Nicolotti, Orazio,Altomare, Cosimo D.
, (2021/01/12)
Thirty-six novel indole-containing compounds, mainly 3-(2-phenylhydrazono) isatins and structurally related 1H-indole-3-carbaldehyde derivatives, were synthesized and assayed as inhibitors of beta amyloid (Aβ) aggregation, a hallmark of pathophysiology of Alzheimer’s disease. The newly synthesized molecules spanned their IC50 values from sub- to two-digit micromolar range, bearing further information into structure-activity relationships. Some of the new compounds showed interesting multitarget activity, by inhibiting monoamine oxidases A and B. A cell-based assay in tau overexpressing bacterial cells disclosed a promising additional activity of some derivatives against tau aggregation. The accumulated data of either about ninety published and thirty-six newly synthesized molecules were used to generate a pharmacophore hypothesis of antiamyloidogenic activity exerted in a wide range of potencies, satisfactorily discriminating the ‘active’ compounds from the ‘inactive’ (poorly active) ones. An atom-based 3D-QSAR model was also derived for about 80% of ‘active’ compounds, i.e., those achieving finite IC50 values lower than 100 μM. The 3D-QSAR model (encompassing 4 PLS factors), featuring acceptable predictive statistics either in the training set (n = 45, q2 = 0.596) and in the external test set (n = 14, r2ext = 0.695), usefully complemented the pharmacophore model by identifying the physicochemical features mainly correlated with the Aβ anti-aggregating potency of the indole and isatin derivatives studied herein.
Synthesis, Characterization and in vitro Antibacterial Evaluation of New Oxindoles and Spiro-Oxindoles Derivatives
Hassan, Mohamed I.,Hassane, Abdallah M.A.
, p. 103 - 113 (2019/12/24)
A RYLIDENES oxindole 3 and 5 were synthesized via the reactions of isatin 1 with malononitrile dimmer 2 and 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile 4. Compound 3 react by Michael addition with malononitrile, ethyl 2-cyanoacetate and acetyl acet
Synthesis, in vitro and in vivo antitumor activity of symmetrical bis-Schiff base derivatives of isatin
Liang, Chengyuan,Xia, Juan,Lei, Dong,Li, Xiang,Yao, Qizheng,Gao, Jing
, p. 742 - 750 (2014/03/21)
Eighteen symmetrical bis-Schiff base derivatives of isatin were synthesized by condensation of the natural or synthetic isatins with hydrazine and were evaluated for their in vitro and in vivo antitumor activities. More than half of the obtained compounds showed potent cytotoxicity according to the MTT assay on five different human cancer cell lines (i.e. HeLa, SGC-7901, HepG2, U251, and A549), with compound 3b 3,3′-(hydrazine-1,2-diylidene)bis (5-methylindolin-2-one) being the most potent compound on HepG2 (IC50 ～ 4.23 μM). 3b was also found to be able to inhibit substantially the tumor growth on the HepS-bearing mice at a dose of 40 mg/kg. The real-time live cell imaging and tracking in the H2B-labeled HeLa cells revealed that 3b could induce mitosis interference and apoptosis-associated cell death. In mechanism study, 3b arrested the cell cycle at the G2/M phase in HepG2 cells by down-regulating the expression of cyclin B1 and cdc 2.
Novel N, N'-Hydrazino-bis-isatin Derivatives with Selective Activity Against Multidrug-Resistant Cancer Cells
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Page/Page column 9-10, (2012/10/08)
The invention is directed to a compound of Formula (I), wherein R is selected from the group consisting of hydrogen atom and unsubstituted or substituted phenyl group; R1 is selected from the group consisting of hydrogen atom and unsubstituted or substituted phenyl group; X is selected from the group consisting of hydrogen atom or halogen atom; and Y is selected from the group consisting of hydrogen atom, halogen atom, C1-C4 alkyl group, nitro group, and —OCF3 group, as well as for its use in therapy, preferably for the treatment of cancer, and to a related pharmaceutical composition, the use of the compound for the manufacture of a medicament for the respective medical indication, and a method of synthesis of the compounds of the invention.
