125473-43-0Relevant articles and documents
Silver-Promoted Fluorination Reactions of α-Bromoamides
Mizuta, Satoshi,Kitamura, Kanami,Kitagawa, Ayako,Yamaguchi, Tomoko,Ishikawa, Takeshi
, p. 5930 - 5935 (2021/02/01)
Silver-promoted C?F bond formation in α-bromoamides by using AgF under mild conditions is reported. This simple method enables access to tertiary, secondary, and primary alkyl fluorides involving biomolecular scaffolds. This transformation is applicable to primary and secondary amides and shows broad functional-group tolerance. Kinetics experiments revealed that the reaction rate increased in the order of 3°>2°>1° α-carbon atom. In addition, it was found that the acidic amide proton plays an important role in accelerating the reaction. Mechanistic studies suggested generation of an aziridinone intermediate that undergoes subsequent nucleophilic addition to form the C?F bond with stereospecificity (i.e., retention of configuration). The synthesis of sterically hindered alcohols and ethers by using AgI is also demonstrated. Examples of reactions of α-bromoamides with O nucleophiles are presented.
Design, synthesis, and evaluation of novel inhibitors for wild-type human serine racemase
Takahara, Satoyuki,Nakagawa, Kiyomi,Uchiyama, Tsugumi,Yoshida, Tomoyuki,Matsumoto, Kazunori,Kawasumi, Yasuo,Mizuguchi, Mineyuki,Obita, Takayuki,Watanabe, Yurie,Hayakawa, Daichi,Gouda, Hiroaki,Mori, Hisashi,Toyooka, Naoki
supporting information, p. 441 - 445 (2017/12/28)
Most of the endogenous free D-serine (about 90%) in the brain is produced by serine racemase (SR). D-Serine in the brain is involved in neurodegenerative disorders and epileptic states as an endogenous co-agonist of the NMDA-type glutamate receptor. Thus, SR inhibitors are expected to be novel therapeutic candidates for the treatment of these disorders. In this study, we solved the crystal structure of wild-type SR, and tried to identify a new inhibitor of SR by in silico screening using the structural information. As a result, we identified two hit compounds by their in vitro evaluations using wild-type SR. Based on the structure of the more potent hit compound 1, we synthesized 15 derivatives and evaluated their inhibitory activities against wild-type SR. Among them, the compound 9C showed relatively high inhibitory potency for wild-type SR. Compound 9C was a more potent inhibitor than compound 24, which was synthesized by our group based upon the structural information of the mutant-type SR.
Synthesis of α-hydroxyl amides via direct amidation of lactic acid at solvent- and catalyst-free conditions
Huang, Meiying,Zhong, Shanshan,Xu, Mengli,Liu, Yunyun
, p. 274 - 276 (2015/06/02)
The efficient synthesis of α-hydroxy-amides has been achieved by the direct amidation of lactic acid using primary amines. The reactions proceed smoothly under solvent-free conditions without using any catalyst. In general, good to excellent yields of products are obtained.
