Synthesis and biological activity of novel mycophenolic acid conjugates containing nitro-acridine/acridone derivatives

Malachowska-Ugarte, Magdalena; Cholewiński, Grzegorz; Dzierzbicka, Krystyna; Trzonkowski, Piotr

doi:10.1016/j.ejmech.2012.04.040

Cited by 33 publications

(17 citation statements)

References 18 publications

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“…The final mycophenolic acid was identical with purchased one (Tocris Bioscience), and we were able to use it in synthesis of the novel analogues of MPA. [34][35][36][37] 1.…”

Section: Resultsmentioning

confidence: 99%

Modifications of total synthesis of mycophenolic acid

Cholewiński¹,

Ugarte²,

Siebert³

et al. 2018

10.5267/j.ccl

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“…The final mycophenolic acid was identical with purchased one (Tocris Bioscience), and we were able to use it in synthesis of the novel analogues of MPA. [34][35][36][37] 1.…”

Section: Resultsmentioning

confidence: 99%

Modifications of total synthesis of mycophenolic acid

Cholewiński¹,

Ugarte²,

Siebert³

et al. 2018

10.5267/j.ccl

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“…1,2,3 Indeed acridines exhibit great pharmaceutical importance due to their potent photodynamic biological activities. 4 However this goes hand-in-hand with its well established toxicity profile 5 of the molecule itself which represents a considerable obstacle to overcome for progression into main stream healthcare.…”

Section: Graphical Abstract Submitted To Tetrahedron Lettersmentioning

confidence: 99%

A rapid, chromatography-free route to substituted acridine–isoalloxazine conjugates under microwave irradiation

Johns

Crouch

Grieve

et al. 2014

Tetrahedron Letters

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“…Additionally, activity can be improved by conjugate forming [38][39][40] . Recently, we reported potent IMPDH inhibitors bearing MPA covalently bonded to nitroacridine/nitroacridone derivatives via amide bond formation 41 . On the other hand, there are also described promising conjugates possessing ester linkages, i.e.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological activity of ester derivatives of mycophenolic acid and acridines/acridones as potential immunosuppressive agents

Cholewiński

Iwaszkiewicz-Grześ

Trzonkowski

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Improved derivatives of mycophenolic acid (MPA) are necessary to reduce the frequency of adverse effects, this drug exerts in treated patients. In this study, MPA was coupled with N-(x-hydroxyalkyl)-9-acridone-4-carboxamides or N-(x-hydroxyalkyl)acridine-4-carboxamides to give respective ester conjugates upon Yamaguchi protocol. This esterification required protection of phenol group in MPA. Designed conjugates revealed higher potency in vitro than parent MPA. Acridine derivatives were more active than acridone analogs and length of the alkyl linker between MPA and heterocyclic units influenced the observed cytotoxicity. Derivatives 2b, 2d, 3a, 3b displayed the most promising immunosuppressive activity.

show abstract

Synthesis and biological activity of novel mycophenolic acid conjugates containing nitro-acridine/acridone derivatives

Cited by 33 publications

References 18 publications

Modifications of total synthesis of mycophenolic acid

Modifications of total synthesis of mycophenolic acid

A rapid, chromatography-free route to substituted acridine–isoalloxazine conjugates under microwave irradiation

Synthesis and biological activity of ester derivatives of mycophenolic acid and acridines/acridones as potential immunosuppressive agents

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