184046-78-4Relevant articles and documents
Synthesis of Azanucleosides by Anodic Oxidation in a Lithium Perchlorate–Nitroalkane Medium and Diversification at the 4′-Nitrogen Position
Shoji, Takao,Kim, Shokaku,Chiba, Kazuhiro
, p. 4011 - 4014 (2017)
Azanucleosides, in which the 4′-oxygen atom has been replaced with a nitrogen atom, have drawn much attention owing to their anticancer and antivirus activity, and tolerance towards nucleases. However, the traditional synthetic strategy requires multiple steps and harsh conditions, thereby limiting the structural and functional diversity of the products. Herein we describe the synthesis of azanucleosides by an electrochemical reaction in a lithium perchlorate–nitroethane medium, followed by postmodification at the 4′-N position. N-Acryloyl prolinol derivatives were converted into azanucleosides by anodic activation of the N-α-C?H bond. Moreover, the use of nitroethane instead of nitromethane lowered the oxidation potential of the N-acryloyl prolinols and increased the Faradic yield. The prepared azanucleosides were efficiently functionalized at the 4′-N-acryloyl group with a lipophilic alkanethiol and a fluorescent dye by conjugate addition and olefin cross-metathesis, respectively.
Stereodivergent Synthesis of 3-Hydroxyprolines and 3-Hydroxypipecolic Acids via Ketoreductase-Catalyzed Dynamic Kinetic Reduction
Prier, Christopher K.,Lo, Michael M.-C.,Li, Hongming,Yasuda, Nobuyoshi
supporting information, p. 5140 - 5143 (2019/11/03)
We report a practical enzymatic approach for the stereoselective synthesis of hydroxylated cyclic amino acids. Using ketoreductases, cyclic ketoesters are converted with high diastereo- and enantioselectivity to all isomers of 3-hydroxyproline and 3-hydroxypipecolic acid via a dynamic kinetic reduction reaction. This work highlights the ability of enzymes to provide solutions to challenges in stereoselective synthesis. (Figure presented.).
Synthesis and Microbiological Evaluation of Novel Tetracyclic Fluoroquinolones
Wagman, Allan S.,Cirz, Ryan,McEnroe, Glenn,Aggen, James,Linsell, Martin S.,Goldblum, Adam A.,Lopez, Sara,Gomez, Marcela,Miller, George,Simons, Lloyd J.,Belliotti, Thomas R.,Harris, Christina R.,Poel, Toni-Jo,Melnick, Michael J.,Gaston, Ricky D.,Moser, Heinz E.
, p. 1687 - 1692 (2017/10/09)
Conformationally constrained tetracyclic fluoroquinolones (FQs) were synthesized and profiled for their microbiological spectrum. The installation of a seven-membered ring between the pyrrolidine substituents and the C8 position on the FQ core scaffold resulted in a remarkable enhancement of microbiological potency toward both Gram-positive and Gram-negative bacteria. Focused optimization of seven-membered ring composition, stereochemistry, and amine placement led to the discovery of the two lead compounds that were selected for further progression.
