The synthesis and structure of a potential immunosuppressant: N-mycophenoyl malonic acid dimethyl ester

The synthesis of a potential immunosuppressant, i.e. dimethyl ester of N-mycophenoyl malonic acid was optimized in the reaction of mycophenolic acid (MPA) with amino malonic dimethyl ester in the presence of propanephosphonic anhydride (T3P) as a coupling reagent. The structural properties of the ob...

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Published inJournal of molecular structure Vol. 1151; pp. 218 - 222
Main Authors Siebert, Agnieszka, Cholewiński, Grzegorz, Garwolińska, Dorota, Olejnik, Adrian, Rachoń, Janusz, Chojnacki, Jarosław
Format Journal Article
LanguageEnglish
Published Elsevier B.V 05.01.2018
Subjects
Amide
Crystal structure
Immunosuppressants
LWYWUEPXPWSLEA-UHFFFAOYSA-N
Mycophenolic acid
Amide
Immunosuppressants
Mycophenolic acid
LWYWUEPXPWSLEA-UHFFFAOYSA-N
Crystal structure
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Summary:The synthesis of a potential immunosuppressant, i.e. dimethyl ester of N-mycophenoyl malonic acid was optimized in the reaction of mycophenolic acid (MPA) with amino malonic dimethyl ester in the presence of propanephosphonic anhydride (T3P) as a coupling reagent. The structural properties of the obtained MPA derivative were investigated by NMR, MS and single crystal X-ray diffraction methods. Theoretical considerations of conformational flexibility based on DFT calculations are presented. [Display omitted] •New compound among mycophenolic acid derivatives, known as immunosuppressants.•Use of propanephosphonic anhydride(T3P) as a coupling agent.•Packing controlled by NH⋯O and stacking interactions.•Conformational analysis based on DFT calculations.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2017.09.041