103127-56-6Relevant articles and documents
Synthesis of N-protection erythro-phenylalanylepoxides
Heinsoo,Raidaru,Linask,Jarv,Zetterstrom,Langel
, p. 2245 - 2247 (1995)
The synthesis of erythro-isomers of N-α-t-Boc, N-α-Fmoc- and N-α-Cbz-L-phenylalanylepoxides from the appropriate N-α-protected L-phenylalanines via bromomethyl-ketone intermediates is described.
Amino acid derived epoxide ring opening under microwave irradiation
Vaiana, Nadia,Rizzi, Luca,Romeo, Sergio
, p. 648 - 649 (2007)
A solvent-free microwave-assisted methodology for the obtainment of the hydroxyethylamine (HEA) isostere is described. A phenylalanine derived aminoalkyl epoxide is allowed to react with a dipeptide amine using basic alumina partially deactivated with water under microwave irradiation. The HEA is obtained in very short time (3 min). This methodology is amenable to application in a parallel or automatic sequential format. Copyright
Synthesis method of (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane
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, (2021/06/23)
The invention relates to the technical field of synthesis of drug intermediates, in particular to a synthesis method of (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane. The method comprises the following steps: condensing N-t-butyloxycarboryl-L-phenylalanine serving as a raw material with substituted phenol under the action of a condensing agent to obtain active ester 15; reacting the active ester 15 with a ylide reagent and alkali to obtain a sulfoxide ylide intermediate 16; reacting the sulfoxide ylide intermediate 16 with halide salt under the action of a catalyst to obtain a halogenated ketone intermediate 6; reducing the halogenated ketone intermediate 6 through a reducing agent under the action of a catalyst to obtain a halogenated methanol intermediate 7; and removing halogen acid from the halogenated methanol intermediate 7 under the action of alkali, and carrying out condensation cyclization to obtain the target product (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane. The synthesis method of the (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane, provided by the invention, has the characteristics of cheap and easily available initial raw materials, safe and controllable process and easiness in operation.
Synthetic method for chiral epoxy compound of anti-HIV drug intermediate
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Paragraph 0043; 0044; 0045, (2016/10/10)
The invention belongs to the field of chemical synthesis and particularly relates to a preparation method for a chiral epoxy compound of an anti-HIV drug intermediate. The method provided by the invention synthesizes the chiral epoxy compound by using a special ligand according to a route represented by the formula. L-phenylalanine used for synthesizing the anti-HIV drug intermediate is low in price and is easily available. The synthetic method is simple and feasible, the yield of the chiral epoxy compound is high, and the synthetic cost of the chiral epoxy compound is obviously lowered compared with that in an existing process.
Plasmepsin inhibitory activity and structure-guided optimization of a potent hydroxyethylamine-based antimalarial hit
Jaudzems, Kristaps,Tars, Kaspars,Maurops, Gundars,Ivdra, Natalija,Otikovs, Martins,Leitans, Janis,Kanepe-Lapsa, Iveta,Domraceva, Ilona,Mutule, Ilze,Trapencieris, Peteris,Blackman, Michael J.,Jirgensons, Aigars
, p. 373 - 377 (2014/05/06)
Antimalarial hit 1SR (TCMDC-134674) identified in a GlaxoSmithKline cell based screening campaign was evaluated for inhibitory activity against the digestive vacuole plasmepsins (Plm I, II, and IV). It was found to be a potent Plm IV inhibitor with no selectivity over Cathepsin D. A cocrystal structure of 1SR bound to Plm II was solved, providing structural insight for the design of more potent and selective analogues. Structure-guided optimization led to the identification of structurally simplified analogues 17 and 18 as low nanomolar inhibitors of both, plasmepsin Plm IV activity and P. falciparum growth in erythrocytes.