155049-17-5Relevant articles and documents
The 1H, 13C, 15N and 117Sn NMR study of the intramolecular Sn-N interaction in tri- and tetraorganotin compounds containing the chiral 2-(4-isopropyl-2-oxazolinyl)-5-phenyl ligand
Cmoch, Piotr,Urbańczyk-Lipkowska, Zofia,Petrosyan, Armine,St?pień, Anita,Staliński, Krzysztof
, p. 29 - 39 (2005)
A series of novel tri- and tetraorganotin compounds containing the optically active 2-(4-isopropyl-2-oxazolinyl)-5-phenyl ligand has been synthesized. All the novel compounds have been characterized, especially by means of the multinuclear NMR investigation, the results of which are discussed. A number of arguments based on the 13C, 15N and 117Sn NMR and X-ray studies support the intramolecular donor-acceptor coordination between tin and nitrogen atoms in the stannanes. For the first time the J(15N-117/119Sn) coupling constant values in coordinated tin hydrides clearly point to a coordination number of the tin larger than four.
Synthesis of 2-oxazolines mediated by N,N′-diisopropylcarbodiimide
Crosignani, Stefano,Young, Abigail C.,Linclau, Bruno
, p. 9611 - 9615 (2004)
Heating N-(β-hydroxyethyl)amides with DIC and Cu(OTf)2 (5 mol %) leads to the formation of 2-oxazolines in good to excellent yields. N-(β-Hydroxy)amides can be cyclised by reaction with diisopropylcarbodiimide (DIC) to give the corresponding 2-
Insights into the antiproliferative mechanism of (C^N)-chelated half-sandwich iridium complexes
Ramos, Robin,Zimbron, Jérémy M.,Thorimbert, Serge,Chamoreau, Lise-Marie,Munier, Annie,Botuha, Candice,Karaiskou, Anthi,Salmain, Michèle,Sobczak-Thépot, Jo?lle
, p. 17635 - 17641 (2020/12/30)
Transition metal-based anticancer compounds, as an alternative to platinum derivatives, are raising scientific interest as they may present distinct although poorly understood mechanisms of action. We used a structure-activity relationship-based methodology to investigate the chemical and biological features of a series of ten (C^N)-chelated half-sandwich iridiumIII complexes of the general formula [IrCp?(phox)Cl], where (phox) is a 2-phenyloxazoline ligand forming a 5-membered metallacycle. This series of compounds undergoes a fast exchange of their chlorido ligand once solubilised in DMSO. They were cytotoxic to HeLa cells with IC50 values in the micromolar range and induced a rapid activation of caspase-3, an apoptosis marker. In vitro, the oxidative power of all the complexes towards NADH was highlighted but only the complexes bearing substituents on the oxazoline ring were able to produce H2O2 at the micromolar range. However, we demonstrated using a powerful HyPer protein redox sensor-based flow cytometry assay that most complexes rapidly raised intracellular levels of H2O2. Hence, this study shows that oxidative stress can partly explain the cytotoxicity of these complexes on the HeLa cell line and gives a first entry to their mechanism of action. This journal is
Benzyne-mediated trichloromethylation of chiral oxazolines
Huang, Xin,Zhao, Weizhao,Chen, De-Li,Zhan, Yaling,Zeng, Tingting,Jin, Huiquan,Peng, Bo
supporting information, p. 2070 - 2073 (2019/02/19)
A three-component reaction between benzyne, oxazolines and chloroform was developed for the synthesis of trichloromethylated chiral oxazolidines. Benzyne not only serves as an electrophile towards oxazolines but also acts as a base for the deprotonation of chloroform. The dual functions of benzyne enable the trichloromethylation of chiral oxazolines and thus construct chiral N,O-quaternary stereocenters.
