83345-44-2Relevant articles and documents
Synthesis of a novel series of 2,3,4-trisubstituted oxazolidines designed by isosteric replacement or rigidification of the structure and cytotoxic evaluation
Andrade, Saulo F.,Teixeira, Claudia S.,Ramos, Jonas P.,Lopes, Marcela S.,Pdua, Rodrigo M.,Oliveira, Mnica C.,Souza-Fagundes, Elaine M.,Alves, Ricardo J.
, p. 1693 - 1699 (2014/12/11)
We have previously reported on a study of the structure-activity relationship in a series of 2,3,4-substituted oxazolidines recently discovered by our group varying the substituent at the ring or stereochemistry of the oxazolidine ring. We discovered the cytotoxic and pro-apoptotic potential of compounds 1 and 2 with good selectivity against cancer cell lines. In the present study we describe the synthesis and cytotoxic evaluation against cancer cell lines (HL60, JURKAT, MDA-MB-231 and LNCaP) of a series of oxazolidines designed by isosteric replacement or rigidification of the oxymethylene spacer of compounds 1 and 2. Alkenes 3 and 4 retained the activity against MDA-MB-231 cells and they were more active on HL60, JURKAT and LNCaP cells. Considering LNCaP cells, E-isomer 4 was at least 7 times and about 3 times more potent than lead 1 and Z-isomer 3, respectively. Compound 4 exerted significant activity against LNCaP with IC50 in the low micromolar range (11 μM) without affecting VERO cells and PBMC proliferation (IC50 > 100 μM) indicating its low toxicity to normal cells.
Heteroarylpyrrolopyridinones active as kinase inhibitors
-
Page/Page column 18, (2008/06/13)
Compounds represented by formula (I) wherein A, R1, R2, R3, R4, R5 and R6 are as defined in the specification or a pharmaceutically acceptable salt or solvate thereof, compositions thereof,
Syntheses of four unusual amino acids, constituents of cyclomarin A
Sugiyama, Hideyuki,Shioiri, Takayuki,Yokokawa, Fumiaki
, p. 3489 - 3492 (2007/10/03)
The stereoselective syntheses of four unusual amino acids, constituents of cyclomarin A, are described. The protected N-methylhydroxyleucine 2 was synthesized using Evans' asymmetric azide-transfer reaction. The unusual amino acid 3 was prepared via diastereoselective methylation of the L-aspartic acid derived lactone 13. The stereoselective formation of threo-β-methoxyphenylalanine 4 was performed via aldol reaction using Scho?llkopf's chiral glycine enolate. The synthesis of N-reverse prenylated tryptophane 5 was achieved by the AQN ligand-promoted Sharpless regioreversed asymmetric aminohydroxylation protocol.
