55120-75-7Relevant articles and documents
The synthesis and complexation of a cobaltocenium-based redox-active cryptand containing the phenanthroline unit
Hall, C.Dennis,Djedovic, Natasha
, p. 8 - 13 (2002)
The synthesis and characterization of a cobaltocenium-based redox-active cryptand 3 containing a phenanthroline unit is described. Complex formation (with Ca2+) was studied by 1H/13C-NMR, and the effects of complexation on the redox properties of 3 were monitored by cyclic voltammetry. The fluorescence spectra of the complexes of 3 and its ferrocene analogue (4) with Eu3+ are also reported, and the low intensity of the fluorescence in each case attributed to carbonyl coordination of Eu3+ rather than metallocene quenching.
Synthesis, Src kinase inhibitory and anticancer activities of 1-substituted 3-(N-alkyl-N-phenylamino)propane-2-ols
Sharma, Deepti,Sharma, Raman K.,Bhatia, Sumati,Tiwari, Rakesh,Mandal, Deendayal,Lehmann, Jessica,Parang, Keykavous,Olsen, Carl E.,Parmar, Virinder S.,Prasad, Ashok K.
body text, p. 1164 - 1172 (2011/11/05)
A series of 3-(N-alkyl-N-phenylamino)propan-2-ol derivatives were synthesized from epichlorohydrine in a multi-step strategy and were evaluated as Src kinase inhibitors. First, epoxy ring opening of epichlorohydrine was carried out in the presence of N-alkylanilines to yield 3-(N-alkyl-N-phenylamino)-1-chloro-propan-2-ol derivatives using Ca(OTf)2 as catalyst based on our previous studies [1]. Second, ring closure was performed under basic conditions to afford N-epoxymethyl N-alkylaniline derivatives. Finally, the epoxide ring opening with four different secondary amines and three nucleobases afforded the final products, i.e., a series of β-amino alcohols. All compounds were screened for their inhibitory activity against Src kinase and anticancer activity on human breast carcinoma cells, BT-20 cell line. Among all compounds, 3-N-methyl-N-phenylamino-1-(pyrrolidin-1-yl)propan-2-ol (13b) exhibited the highest inhibitory potency (IC50 = 66.1 μM) against Src kinase. Structure-activity relationship studies suggested that the incorporation of bulky groups at position 1 and N-substitution with groups larger than methyl moiety, reduced the inhibitory potency of the compound significantly. Compounds 3-(N-ethyl-N-phenylamino-)-1-(4-methylpiperazin-1-yl)propan-2-ol (14c) and 3-(N-ethyl-N-phenylamino)-1-(thymine-1-yl)propan-2-ol (17) were found to inhibit the growth of breast carcinoma cells by approximately 45-49% at concentration of 50 μM.
Regiospecific Ring Opening of Epoxides with Cyanotrimethylsilane on Solid Bases: Reaction Features, and Role of Metal Cations of Solid Bases
Sugita, Keisuke,Ohta, Akihisa,Onaka, Makoto,Izumi, Yusuke
, p. 1792 - 1799 (2007/10/02)
A new attempt of utilizing solid acids and bases for ring opening of epoxides with Me3SiCN was investigated.Solid strong bases such as calcium oxide and magnesium oxide catalyzed the regio- and chemoselective ring opening of epoxides with Me3SiCN much more effectively than homogeneous catalysts.On CaO and MgO, the reactions of unsymmetrical epoxides with Me3SiCN afforded 3-trimethylsiloxyalkanenitriles in high yields through regio- and stereoselective attack of cyanide ion on the less substituted epoxycarbon.Additionally, on CaO, 2,3-epoxy-1-alkanol derivatives were selectively converted to the corresponding C-3 opened products by the attack of cyanide ion.In these cases no isocyanides were formed.It was suggested that CaO acted as a bifunctional catalyst; the lattice oxide anions of CaO activated Me3SiCN, and simultaneously calcium ions promoted the ring opening of epoxyalkanol as Lewis acid sites.
