1372610-45-1Relevant academic research and scientific papers
Synthesis and crystal structure of a chiral lactam and three amino alcohols as potential protein tyrosine phosphates 1B inhibitors
?zhan Kocakaya, ?afak,Karakaplan, Mehmet,Scopelliti, Rosario
, p. 1342 - 1349 (2017/10/13)
Chiral lactam 2 and three chiral β-amino alcohols 3–5 have been synthesized and characterized by spectroscopic techniques. Regioselective ring opening reaction of chiral styrene oxide by an amine nucleophile was confirmed by X-ray diffraction data. Ligand 2–4 crystallizes in the tetragonal, orthorhombic and tetragonal crystal lattice system respectively. Ligands 2–6 have been used as potential inhibitors for protein tyrosine phosphatase 1B enzyme (PTP1B). The potential inhibitor effect of these molecules to the target protein was investigated by Dock and molecular dynamics calculations. Dock score analysis and Lipinski parameters suggested that ligands 1, 2, 4–6 are potential inhibitors towards PTP1B, thus indicating that the residues Arg24, Arg254 and Met258, Asp29 in the second active site of PTP1B are essential for the high selectivity of inhibitors. The results indicate that the polar hydrogen bonding interacts with Asp29, Gln102, and the amino acid residues of PTP1B are responsible for governing inhibitory potency of ligands 1–6.
Synthesis of new diaza-18-crown-6 ethers derived from trans-(R,R)-1,2- diaminocyclohexane and investigation of their enantiomeric discrimination ability with amino acid ester salts
Karakaplan, Mehmet,Ak, Devran,?olak, Mehmet,Kocakaya, ?afak ?zhan,Ho?g?ren, Halil,Pirin??io?lu, Necmettin
, p. 349 - 358 (2013/01/15)
The synthesis of four diaza-18-crown-6 ethers with C2-symmetry derived from trans-(R,R)-1,2-diaminocyclohexane bearing methyl, phenyl and phenoxymethyl moeities attached to a stereogenic centre on the crown ring were achieved. Enantiomeric discrimination of these macrocycles against amino acid methyl ester salts was examined by 1H NMR titration method. They exhibit strong binding ability and some of them show a very high enantioselectivity towards amino acid esters, corresponding to 5.37 kJ/mol of binding energy difference in CDCl3 at 25 °C. Computational modelling showed parallel results with experimental calculations, thus providing a detailed understanding of molecular recognition mode and binding sites between the hosts and the guests.
Asymmetric organocatalytic efficiency of synthesized chiral β-amino alcohols in ring-opening of glycidol with phenols
Aral, Tarik,Karakaplan, Mehmet,Hosgoeren, Halil
experimental part, p. 794 - 802 (2012/08/28)
A series of novel chiral β-amino alcohols 3-5 and 7-10 were synthesized by regioselective ring opening of epoxides and chiral amines with a straightforward method in high yields (up to 99 %). Kinetic resolution of racemic glycidol with phenols was achieved by using chiral amino alcohols as organocatalysts. Amino alcohols 5, 8 and 10 exhibited the highest enantioselectivities with p-cresol, phenol, and p-methoxyphenol by 63, 65, 58 % ee, respectively. The moderate enantioselectivities were observed with catalyst 9b towards all the nucleophiles (34-48 % ee). The ee values of the desired 3-aryloxy-1, 2-diols were determined by HPLC. This study presents an attractive tool for the synthesis of β-blockers and structurally complex molecules.
