40149-67-5Relevant articles and documents
A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (-)-Deoxynupharidine
Moran, Wesley J.,Goodenough, Katharine M.,Raubo, Piotr,Harrity, Joseph P. A.
, p. 3427 - 3429 (2003)
(Equation presented) A stereocontrolled route to Nuphar alkaloids is described that employs a formal [3 + 3] cycloaddition strategy to assemble the piperidine nucleus. The addition of Pd-TMM complexes to aziridine 10 was found to be sluggish; however, the addition of a functionalized allyl Grignard reagent followed by a Mitsunobu condensation reaction provided 11 in high yield. The employment of this route in the formal synthesis of (-)-deoxynupharidine 1 is described.
Enzymatic methods for the preparation of enantiopure malic and aspartic acid derivatives in organic solvents
Liljeblad, Arto,Kanerva, Liisa T.
, p. 4405 - 4415 (1999)
The kinetic resolution of malic and aspartic acid diesters as well as of its N-butanoyl dimethyl ester by highly regioselective lipases and acylase I enzymes were studied. Candida antarctica lipase A on Celite catalyzed the enantioselective acylation of the hydroxyl and amino groups. Acylase I from Aspergillus melleus and Candida antarctica lipase B catalyzed the enantioselective alcoholyses of the ester groups at the α- and β-positions, respectively. (C) 1999 Elsevier Science Ltd.
β-Hydroxy- A nd β-Aminophosphonate Acyclonucleosides as Potent Inhibitors of Plasmodium falciparum Growth
Cheviet, Thomas,Wein, Sharon,Bourchenin, Gabriel,Lagacherie, Manon,Périgaud, Christian,Cerdan, Rachel,Peyrottes, Suzanne
, p. 8069 - 8087 (2020/08/12)
Malaria is an infectious disease caused by a parasite of the genus Plasmodium, and the emergence of parasites resistant to all current antimalarial drugs highlights the urgency of having new classes of molecules. We developed an effective method for the synthesis of a series of β-modified acyclonucleoside phosphonate (ANP) derivatives, using commercially available and inexpensive materials (i.e., aspartic acid and purine heterocycles). Their biological evaluation in cell culture experiments and SAR revealed that the compounds' effectiveness depends on the presence of a hydroxyl group, the chain length (four carbons), and the nature of the nucleobase (guanine). The most active derivative inhibits the growth of Plasmodium falcIParum in vitro in the nanomolar range (IC50 = 74 nM) with high selectivity index (SI > 1350). This compound also showed remarkable in vivo activity in P. berghei-infected mice (ED50 ～0.5 mg/kg) when administered by the IP route and is, although less efficient, still active via the oral route. It is the first ANP derivative with such potent antimalarial activity and therefore has considerable potential for development as a new antimalarial drug.
D-asparaginic acid preparation method
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Paragraph 0025, (2016/11/28)
The invention discloses a D-asparaginic acid preparation method. The configuration inversion technology is adopted, and the preparation method comprises the steps that L-dimethyl malate-2-besilate can be formed by generating L-dimethyl malate through L-malic acid and then making the L-dimethyl malate react with benzene sulfonyl chloride, then the L-dimethyl malate-2-besilate is made to react with phthalimide potassium, and benzenesulfonic acid serves as a good removal agent, so that D- dimethyl aspartate-2-phthalimide is formed, hydrolysis is conducted under the alkaline condition, D-disodium aspartate is generated, after passing through cation exchange resin, effluent is subjected to concentration, and ethyl alcohol with the concentration being 95% is added for crystallization, so that D-asparaginic acid is obtained. By means of the method, neither high temperature nor high pressure is needed, resolution is not needed, environmental pollution is not caused, and the yield can reach 75% and above.
