478615-35-9Relevant academic research and scientific papers
Synthesis of oxazolidinone from enantiomerically enriched allylic alcohols and determination of their molecular docking and biologic activities
Atmaca, Ufuk,Kaya, Rüya,Karaman, Halide Sedef,?elik, Murat,Gül?in, ?lhami
, (2019/06/08)
Enantioselective synthesis of functionalized cyclic allylic alcohols via kinetic resolution in transesterifcation with different lipase enzymes has been developed. The influence of the enzymes and temperature activity was studied. By determination of ideal reaction conditions, byproduct formation is minimized; this made it possible to prepare enantiomerically enriched allylic alcohols in high ee's and good yields. Enantiomerically enriched allylic alcohols were used for enantiomerically enriched oxazolidinone synthesis. Using benzoate as a leaving group means that 1 mol % of potassium osmate is necessary and can be obtained high yields 98%. Inhibitory activities of enantiomerically enriched oxazolidinones (8, 10 and 12) were tested against human carbonic anhydrase I and II isoenzymes (hCA I and hCA II), acetylcholinesterase (AChE), and α-glycosidase (α-Gly) enzymes. These enantiomerically enriched oxazolidinones derivatives had Ki values in the range of 11.6 ± 2.1–66.4 ± 22.7 nM for hCA I, 34.1 ± 6.7–45.2 ± 12.9 nM for hCA II, 16.5 ± 2.9 to 35.6 ± 13.9 for AChE, and 22.3 ± 6.0–70.9 ± 9.9 nM for α-glycosidase enzyme. Moreover, they had high binding affinity with ?5.767, ?6.568, ?9.014, and ?8.563 kcal/mol for hCA I, hCA II, AChE and α-glycosidase enzyme, respectively. These results strongly supported the promising nature of the enantiomerically enriched oxazolidinones as selective hCA, AChE, and α-glycosidase inhibitors. Overall, due to these derivatives’ inhibitory potential on the tested enzymes, they are promising drug candidates for the treatment of diseases like glaucoma, leukemia, epilepsy; Alzheimer's disease; type-2 diabetes mellitus that are associated with high enzymatic activity of CA, AChE, and α-glycosidase.
Tethered aminohydroxylation: Dramatic improvements to the process
Donohoe, Timothy J.,Bataille, Carole J. R.,Gattrell, William,Kloesges, Johannes,Rossignol, Emilie
, p. 1725 - 1728 (2008/02/02)
Changing the identity of the N leaving group on a hydroxylamine-based reoxidant gives a dramatic improvement to the tethered aminohydroxylation reaction. Using OCOC6F5 as a leaving group means that only 1 mol % of osmium is required and yields as high as 98% can be obtained. Acyclic homoallylic alcohols were substrates considered too unreactive for effective use in the tethered aminohydroxylation reaction; improved reaction conditions mean that they have now become viable substrates for oxidation.
N-sulfonyloxy carbamates as reoxidants for the tethered aminohydroxylation reaction
Donohoe, Timothy J.,Chughtai, Majid J.,Klauber, David J.,Griffin, David,Campbell, Andrew D.
, p. 2514 - 2515 (2007/10/03)
The use of N-sulfonyloxy carbamates as reoxidants for the tethered aminohydroxylation (TA) reaction is reported. These new conditions obviate the requirement for lithium hydroxide and tBuOCl in the oxidation mixture. In addition to providing aminohydroxyl
The tethered aminohydroxylation (TA) of cyclic allylic carbamates
Donohoe, Timothy J.,Johnson, Peter D.,Cowley, Andrew,Keenan, Martine
, p. 12934 - 12935 (2007/10/03)
The tethered aminohydroxylation of cyclic allylic carbamates is described using catalytic amounts of potassium osmate. The mechanism of reaction involves formation of an imido-osmium complex which adds intramolecularly to alkenes with complete control of
Synthesis of Protected Aminocyclohexanediols
Knapp, Spencer,Patel, Dinesh V.
, p. 5072 - 5076 (2007/10/02)
As the model study for the synthesis of aminocyclitols and amino sugars, 2-cyclohexen-1-ol (1) was converted to five of the seven possible (1,2,3)-aminocyclohexanediols in protected form (4a, 6a, 11a, 13a, and 18a).Two flexible new approaches were employe
