1259379-29-7Relevant articles and documents
In vitro cytotoxicity evaluation of some substituted isatin derivatives
Vine, Kara L.,Locke, Julie M.,Ranson, Marie,Benkendorff, Kirsten,Pyne, Stephen G.,Bremner, John B.
, p. 931 - 938 (2007)
A range of substituted 1H-indole-2,3-diones (isatins) were synthesized using standard procedures and their cytotoxicity evaluated against the human monocyte-like histiocytic lymphoma (U937) cell line in vitro. SAR studies identified C5, C6
Chemistry of phosphorus ylides. Part 37. The reaction of phosphonium ylides with indoles and naphthofurans. Synthesis of phosphanylidenes, pyrans, cyclobutenes, and pyridazine as antitumor agents
Maigali, Soher S.,El-Hussieny, Marwa,Soliman, Fouad M.
, p. 15 - 23 (2015)
The reaction of the stabilized phosphonium ylides 2a, b with indolinones 1a, b and naphthofuranone 13 afforded the corresponding propylidene and ethylidene derivatives 4a-d and 14a, b. On the other hand, the active phosphacumulenes 5a, b react with compounds 4a-d by [4 + 2]-cycloaddition to give the stable phosphanylidene indole pyranones 6a-h. Although compounds 14a, b afforded the naphthofuropyrans 16a-d and triphenylphosphane. Moreover, the phosphallene ylide 7 react with compounds 4a-d and 14a, b to give phosphanylidenecyclobuteneindoline 9a-d and naphthalenones 18a, b, respectively. In addition, the naphthofuropyridazine 21 was obtained from the reaction of the hydrazone 19 and the phosphacumulene 5a. The antitumor activity of some of the new compounds was evaluated, in vitro, against colon and hepatocellular carcinoma cell lines. They showed values closed to that recorded by the reference drug Doxorubicin.
Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1
Paul, Saurav,Roy, Ashalata,Deka, Suman Jyoti,Panda, Subhankar,Srivastava, Gopal Narayan,Trivedi, Vishal,Manna, Debasis
, p. 1640 - 1654 (2017/08/22)
Indoleamine 2,3-dioxygenase 1 (IDO1) is considered as an important therapeutic target for the treatment of cancer, chronic infections and other diseases that are associated with immune suppression. Recent developments in understanding the catalytic mechanism of the IDO1 enzyme revealed that conversion of l-tryptophan (l-Trp) to N-formylkynurenine proceeded through an epoxide intermediate state. Accordingly, we synthesized a series of 3-substituted oxindoles from l-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to l-Trp. These potent compounds also showed IDO1 inhibition potencies in the low-micromolar range (IC50 = 0.33-0.49 μM) in MDA-MB-231 cells. The cytotoxicity of these potent compounds was trivial in different model cancer (MDA-MB-231, A549 and HeLa) cells and macrophage (J774A.1) cells. Stronger selectivity for the IDO1 enzyme (124 to 210-fold) over the tryptophan 2,3-dioxygenase (TDO) enzyme was also observed for these compounds. These results suggest that the oxindole moiety of the compounds could mimic the epoxide intermediate state of l-Trp. Therefore, the structural simplicity and low-micromolar inhibition potencies of these 3-substituted oxindoles make them quite attractive for further investigation of IDO1 function and immunotherapeutic applications.
Action of Hydrazines on 2-(2-Oxindolin-3-ylidene)malononitrile, (E,Z)-Ethyl 2-cyano-2-(2-oxindolin-3-ylidene)acetate and Isatin-β-thiosemicarbazone as a Source of Spiro Indoline-pyrazole Systems
Youssef, Ahmed S. A.,Hemdan, Magdy M.,Emara, Samir A.,Kamel, Rabaa M.
, p. 1331 - 1336 (2015/10/06)
2-(2-Oxindolin-3-ylidene)malononitrile (1a) or (E,Z)-ethyl 2-cyano-2-(2-oxindolin-3-ylidene)acetate (1b) or isatin-β-thiosemicarbazone (1c) undergoes reactions with prototype hydrazine hydrate itself and some of its simple congeners to give hydrazone derivatives bearing indoline-2-one moiety (2). The hydrazone derivatives (2) when heated with acetyl acetone or ethyl acetoacetate in dry pyridine afforded the spiro indoline derivatives (3a, 3b). Also, cinnoline derivative (9) is obtained by action of hydrazine hydrate on the N-acetyl derivative of (6a). The structures of the newly synthesized compounds were evaluated by IR, 1H-NMR spectroscopy, mass spectra and elemental analyses.
