33829-02-6Relevant articles and documents
One-pot solvent free, green route to novel substituted spiro[oxindole-isoxazolidine] derivatives: novel candidates as antimicrobial agents
KAUR, MANPREET,BHATIA, SUMEET KAUR,SINGH, BALDEV
, p. 1299 - 1303 (2021/06/09)
The environmentally benign catalyst and solvent-free synthesis of ketonitrones may not always be accomplished by simple condensation reactions. The occasional reports of green synthetic routes toward these compounds have been reported. The key features of
Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines]
Akaev, Andrey A.,Bezzubov, Stanislav I.,Desyatkin, Victor G.,Vorobyeva, Nataliya S.,Majouga, Alexander G.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
, p. 3340 - 3356 (2019/03/11)
A novel stereocontrolled assembly of spiro[oxindole-3,2′-pyrrolidines] via [3+2]-cycloaddition of donor-acceptor cyclopropanes to electron-poor ketimines, iminooxindoles, was developed. The method allows for efficient employment of common readily available donor-acceptor cyclopropanes, functionalized with ester, keto, nitro, cyano etc. groups, and N-unprotected iminooxindoles. The stereospecificity of the initial SN2-like imine attack on a cyclopropane molecule together with a high diastereoselectivity of further C-C bond formation facilitate a rapid access to spiro[oxindole-3,2′-pyrrolidines] in their optically active forms. Preliminary in vitro testing of the synthesized compounds against LNCaP (p53+) and PC-3 (p53-) cells revealed good antiproliferative activities and p53-selectivity indices for several compounds that are intriguing in terms of their further investigation as inhibitors of MDM2-p53 interaction.
Spirotriazoline oxindoles: A novel chemical scaffold with in vitro anticancer properties
Ribeiro, Carlos J.A.,Nunes, Rute C.,Amaral, Joana D.,Gon?alves, Lídia M.,Rodrigues, Cecília M.P.,Moreira, Rui,Santos, Maria M.M.
, p. 494 - 509 (2017/10/10)
The design and synthesis of a library of twenty-six spirotriazoline oxindoles and their in vitro evaluation as potential anticancer agents is reported. The antiproliferative activity of the synthesized compounds was assessed against four different cancer cell lines (HCT-116 p53 (+/+), HCT-116 p53 (?/?), MCF-7, and MDA-MB-231). Four spirotriazoline oxindoles showed selectivity against the four cancer cell lines tested over the non-cancer derived HEK 293T cell line. To characterize the molecular mechanisms involved in compound antitumoral activity, two spirotriazoline oxindoles were selected for further studies. Both compounds were able to induce apoptosis and cell cycle arrest at G0/G1 phase and upregulated p53 steady-state levels, while decreasing its main inhibitor MDM2, in HCT-116 cells. Importantly, cytotoxic effects induced by spirotriazoline oxindoles occurred in cancer cells without eliciting cell death in non-malignant CCD-18Co human colon fibroblasts. In addition, four spirotriazoline oxindoles showed selectivity against the triple-negative breast cancer cell line MDA-MB-231 with IC50 values of 3.5–6.7 μM. These results highlight the anticancer potential of spirotriazoline oxindoles, especially when dealing with aggressive and challenging triple-negative breast cancer.
Ambient temperature synthesis of spiro[indoline-3,2′-thiazolidinones] by a DBSA-catalyzed sequential reaction in water
Preetam, Amreeta,Nath, Mahendra
supporting information, p. 1502 - 1506 (2016/03/12)
An energy-efficient eco-friendly methodology for the synthesis of a series of pharmacologically important spiro[indoline-3,2′-thiazolidinones] has been developed by the reaction of primary amines with various isatin derivatives and thioglycolic acid in the presence of p-dodecylbenzenesulfonic acid (DBSA) as an efficient Br?nsted acid surfactant combined catalyst in aqueous medium at 25 °C. This synthetic protocol demonstrates several advantages such as operational simplicity, energy-efficiency, good to excellent isolated yields, and the use of a preferred green solvent system for the preparation of desired products.
Remote activation of the nucleophilicity of isatin
Zari, Sergei,Kudrjashova, Marina,Pehk, Tonis,Lopp, Margus,Kanger, Tonis
supporting information, p. 1740 - 1743 (2014/04/17)
The concept of the remote activation of reactivity was first applied in asymmetric organocatalysis. An isatin 3-phenylimine derivative acts as a donor in the thiourea catalyzed asymmetric addition to unsaturated 1,4-ketoesters, affording aza-Michael adducts in high enantiomeric purity and yield.
Facile and highly diastereoselective synthesis of 3-aminooxindoles via AgOAc-catalyzed vinylogous Mannich reaction
Shi, Yu-Hua,Wang, Zheng,Shi, Ying,Deng, Wei-Ping
experimental part, p. 3649 - 3653 (2012/06/18)
A novel AgOAc-catalyzed vinylogous Mannich reaction between easily prepared imines 1 derived from isatins and trimethylsilyloxyfuran 2 (TMSOF) was developed. This method provided a facile synthetic route to get access to synthetically useful quaternary 3-aminooxindole in excellent yields (94-99%) and diastereoselectivities (>99:1).
On antimicrobial activity of 3'-phenylspiro[3H-indole-3,2'-thiazolidine]-2,4' (1H)-diones
Diurno,Mazzoni,Piscopo,Bolognese
, p. 435 - 441 (2007/10/02)
3'-substituted phenylspiro[3H-indole-3,2'-thiazolidine]-2,4' (1H)-diones (1-15), tested toward Gram-positive, Gram-negative bacteria and Fungi, showed a significant activity against Gram-positive bacteria.
