134454-19-6Relevant articles and documents
A parallel preparation of a bicyclic N-chiral amine library and its use for chiral catalyst screening
Uozumi, Yasuhiro,Mizutani, Kanako,Nagai, Shin-ichi
, p. 407 - 410 (2001)
A parallel library of optically active bicyclic tertiary amines bearing N-chiral bridgehead nitrogen atoms was readily prepared by condensation of primary amines, cyclic amino acids and aldehydes. The enantiocontrolling ability of each of the library members was examined for the asymmetric alkylation of benzaldehyde with diethylzinc, and (3R,6R,7aS)-(2,3-diphenyl-6-hydroxy)hexahydro-1H-pyrrolo[1,2-c]imidazol-1- one, which contains a β-amino alcohol unit, showed high enantioselectivity.
Synthesis of a Bicyclic Azetidine with in Vivo Antimalarial Activity Enabled by Stereospecific, Directed C(sp3)-H Arylation
Maetani, Micah,Zoller, Jochen,Melillo, Bruno,Verho, Oscar,Kato, Nobutaka,Pu, Jun,Comer, Eamon,Schreiber, Stuart L.
, p. 11300 - 11306 (2017)
The development of new antimalarial therapeutics is necessary to address the increasing resistance to current drugs. Bicyclic azetidines targeting Plasmodium falciparum phenylalanyl-tRNA synthetase comprise one promising new class of antimalarials, especially due to their activities against three stages of the parasite's life cycle, but a lengthy synthetic route to these compounds may affect the feasibility of delivering new therapeutic agents within the cost constraints of antimalarial drugs. Here, we report an efficient synthesis of antimalarial compound BRD3914 (EC50 = 15 nM) that hinges on a Pd-catalyzed, directed C(sp3)-H arylation of azetidines at the C3 position. This newly developed protocol exhibits a broad substrate scope and provides access to valuable, stereochemically defined building blocks. BRD3914 was evaluated in P. falciparum-infected mice, providing a cure after four oral doses.
TFA-protected α-amino acid N-hydroxysuccinimide ester: Application for inter- And intramolecular acylation
Tachrim, Zetryana Puteri,Oida, Kazuhiro,Ohashi, Fumina,Wakasa, Haruna,Ikemoto, Haruka,Kurokawa, Natsumi,Sakihama, Yasuko,Hashidoko, Yasuyuki,Suzuki, Takeyuki,Hashimoto, Makoto
, p. 877 - 893 (2019/04/26)
The utilization of N-trifluoroacetyl (TFA)-α-amino acid N-hydroxysuccinimide ester (OSu) derivatives, a promising acylating agent with high storage stability, is reported for Friedel-Crafts acylation into arenes and N-heterocycles. The reaction between TF
Discovery and structure-activity relationships of 2-benzylpyrrolidine- substituted aryloxypropanols as calcium-sensing receptor antagonists
Yang, Wu,Wang, Yufeng,Roberge, Jacques Y.,Ma, Zhengping,Liu, Yalei,Lawrence, R. Michael,Rotella, David P.,Seethala, Ramakrishna,Feyen, Jean H. M.,Dickson Jr., John K.
, p. 1225 - 1228 (2007/10/03)
A structure-activity relationship study of the amine portion of the calcilytic compound NPS-2143 resulted in the discovery of substituted 2-benzylpyrrolidines as replacements for the 1,1-dimethyl-2-naphthalen-2-yl- ethylamine. When compared to NPS-2143, a
