Selective synthesis of fluorinated benzyl- or phenylpyrimidines from the heterocyclisation of α-trifluoroacetylarylpropanenitriles

Selective Synthesis of Fluorinated Benzyl-or Phenylpyrimidines from the Heterocyclization of α-Trifluoroacetylarylpropanenitriles. -The new method allows the preparation of fluorinated phenyl-or benzylpyrimidines, analogues of trimethoprim and pyrimethamine, simply by varying the nature of the solvent. For example, heterocyclization of enol ethers (III) with guanidine (IV) in methanol provides the phenylpyrimidines (V) whereas the same reaction carried out in acetonitrile affords benzylpyrimidines (VII). The synthetic approach to phenylpyrimidine (XII) is adopted from a previously reported method. Concerning the bioactivity of pyrimidines (Vb) and (XI) on T. gondii, they reveal activity comparable to that of trimethoprim but they are less active than pyrimethamine. -(BERBER*, H.; MIRAND, C.; DEROUIN, F.; J.

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Selective Synthesis of Fluorinated Benzyl‐ or Phenylpyrimidines from the Heterocyclization of α‐Trifluoroacetylarylpropanenitriles.

Berber

Mirand

Derouin

2007

ChemInform

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Synthesis and evaluation of new 2,6-diamino-5-hetarylpyrimidines as inhibitors of dihydrofolate reductase

et al. 2017

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Novel approaches to screening guanidine derivatives

Rauf¹,

Imtiaz‐ud‐Din²,

Badshah³

2013

Expert Opinion on Drug Discovery

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Guanidines, as they are both organically based and also hydrophilic in nature, have undergone a mammoth amount of screening and testing to discover promising lead structures with a CN3 core, appropriate for potential future drug development. The compounds have the potential to be neurodegenerative therapeutic options, as well as: anti-inflammatory, anti-protozoal, anti-HIV, chemotherapeutic, anti-diabetic agents and so on. It is true that guanidine-based compounds of natural sources also, like synthetic and virtually designed drugs, have been of significant interest and have the potential to be useful therapeutic options in the future. As for now, however, there is not sufficient data to support their use in a number of the suggested areas, and further studies are required.

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Selective synthesis of fluorinated benzyl- or phenylpyrimidines from the heterocyclisation of α-trifluoroacetylarylpropanenitriles

Cited by 3 publications

References 30 publications

Selective Synthesis of Fluorinated Benzyl‐ or Phenylpyrimidines from the Heterocyclization of α‐Trifluoroacetylarylpropanenitriles.

Selective Synthesis of Fluorinated Benzyl‐ or Phenylpyrimidines from the Heterocyclization of α‐Trifluoroacetylarylpropanenitriles.

Synthesis and evaluation of new 2,6-diamino-5-hetarylpyrimidines as inhibitors of dihydrofolate reductase

Novel approaches to screening guanidine derivatives

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