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Chemical Structure| 63837-12-7 Chemical Structure| 63837-12-7

Structure of 63837-12-7

Chemical Structure| 63837-12-7

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Product Citations

Product Citations

Walczak, Juliusz Maksymilian ; Iwaszkiewicz-Grzes, Dorota ; Ziomkowska, Michalina ; Sliwka-Kaszynska, Magdalena ; Dasko, Mateusz ; Trzonkowski, Piotr , et al.

Abstract: The group of 18 new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5′-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis of 14 of them employed uronium-type activating system (TBTU/HOBt/DIPEA) while 4 of them concerned phosphonic acid anhydride method (T3P/Py) facilitating amides to be obtained in moderate to excellent yields without the need of phenolic group protection. Most of optimised protocols did not require complicated reaction work-ups, including chromatographic, solvent-consuming methods. The biological activity assay was performed on the T-Jurkat cell line and peripheral mononuclear blood cells (PBMCs) which are both dedicated for antiproliferative activity determination. Each of designed derivatives was characterised by reduced cytotoxicity and benzoxazole analogue (A2) revealed the most promising activity. Subsequently, an observed structure-activity relationship was discussed.

Keywords: Mycophenolic acid ; amide derivatives ; heterocycles ; benzoxazole ; IMPDH inhibition

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Product Details of [ 63837-12-7 ]

CAS No. :63837-12-7
Formula : C7H6N2O
M.W : 134.14
SMILES Code : NC1=CC=C(OC=N2)C2=C1
MDL No. :MFCD05256201
InChI Key :IAWQUHCVFXQBMC-UHFFFAOYSA-N
Pubchem ID :1482188

Safety of [ 63837-12-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 63837-12-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 63837-12-7 ]

[ 63837-12-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 7205-46-1 ]
  • [ 63837-12-7 ]
  • [ 1449515-40-5 ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; for 15h;Reflux; General procedure: To a solution of intermediate 2 (14.9 mmol) in dioxane (100 mL) is added the corresponding aniline (22.4 mmol), cesium carbonate (22.4 mmol), BetaGammaNuAlphaRho (0.9 mmol) a n d tris(dibenzylideneacetone)dipalladium (0.45 mmol). The reaction mixture is refluxed for 15 h, filtered on Celite, evaporated to dryness and purified on silica gel to give the desired compound
 

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