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 in | Journal of molecular structure Vol. 1151; pp. 218 - 222 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier B.V
05.01.2018
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| Abstract | 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.
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•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. |
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| AbstractList | 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. |
| Author | Siebert, Agnieszka Chojnacki, Jarosław Cholewiński, Grzegorz Olejnik, Adrian Rachoń, Janusz Garwolińska, Dorota |
| Author_xml | – sequence: 1 givenname: Agnieszka surname: Siebert fullname: Siebert, Agnieszka organization: Department of Organic Chemistry, Gdansk University of Technology, G. Narutowicza 11/12, Gdansk, PL-80233, Poland – sequence: 2 givenname: Grzegorz surname: Cholewiński fullname: Cholewiński, Grzegorz organization: Department of Organic Chemistry, Gdansk University of Technology, G. Narutowicza 11/12, Gdansk, PL-80233, Poland – sequence: 3 givenname: Dorota surname: Garwolińska fullname: Garwolińska, Dorota organization: Department of Organic Chemistry, Gdansk University of Technology, G. Narutowicza 11/12, Gdansk, PL-80233, Poland – sequence: 4 givenname: Adrian orcidid: 0000-0002-1807-8995 surname: Olejnik fullname: Olejnik, Adrian organization: Department of Inorganic Chemistry, Gdansk University of Technology, G. Narutowicza 11/12, Gdansk, PL-80233, Poland – sequence: 5 givenname: Janusz surname: Rachoń fullname: Rachoń, Janusz organization: Department of Organic Chemistry, Gdansk University of Technology, G. Narutowicza 11/12, Gdansk, PL-80233, Poland – sequence: 6 givenname: Jarosław orcidid: 0000-0002-2453-8214 surname: Chojnacki fullname: Chojnacki, Jarosław email: jaroslaw.chojnacki@pg.gda.pl organization: Department of Inorganic Chemistry, Gdansk University of Technology, G. Narutowicza 11/12, Gdansk, PL-80233, Poland |
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| Title | The synthesis and structure of a potential immunosuppressant: N-mycophenoyl malonic acid dimethyl ester |
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