Novel pyrrolo[2,3-d]pyrimidine derivatives: Design, synthesis, structure elucidation and in vitro anti-BVDV activity

The progression of drug resistance of viral infection justifies the discovering of new anti-viral agents. Thus, a novel series of pyrrolopyrimidine derivatives 5–7 and 9–18 were designed, synthesized and fully characterized by IR, mass spectroscopy, NMR, and elemental analysis. The structure of 4,6-...

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Veröffentlicht in:Tetrahedron 2019-12, Vol.75 (51), p.130749, Article 130749
Hauptverfasser: Sroor, Farid M., Basyouni, Wahid M., Tohamy, Wael M., Abdelhafez, Tawfeek H., El-awady, Mostafa K.
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Sprache:eng
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Zusammenfassung:The progression of drug resistance of viral infection justifies the discovering of new anti-viral agents. Thus, a novel series of pyrrolopyrimidine derivatives 5–7 and 9–18 were designed, synthesized and fully characterized by IR, mass spectroscopy, NMR, and elemental analysis. The structure of 4,6-dichloro-pyrrolo[2,3-d]pyrimidine 10 elucidated by single crystal X-ray diffraction. Herein, we reported the first pyrrolo[2,3-d]pyrimidine compounds with trichloromethane at position 2 of the pyrimidine ring. As initial biological activity screening, evaluation of the pyrrolo[2,3-d]pyrimidine compounds as anti-BVDV (Bovine Viral Diarrhea Virus) was examined. The compounds 11, 13, 16 and 17 exhibited excellent activity as a potent inhibitor against BVDV. Structure activity relationship showed that the pyrrolo[2,3-d]pyrimidine molecules presenting hydrogen atom or trichloromethyl group on C2 and chlorine, sulfur, pyrrolidine or methoxy groups on C4 of the pyrimidine ring showed high activity as anti-BVDV in comparison with the compounds which have Cl or CH3 on C2 position. [Display omitted] •Synthesizing of novel 6-chloro-2-trichloromethyl-pyrrolo[2,3-d]pyrimidine derivatives.•First pyrrolo[2,3-d]pyrimidine scaffolds with CCl3 in position 2 (C2) has been reported.•Anti-BVDV activity was studied.•The most active compounds which have CCl3 or Cl in the position 2 of pyrimidine ring 11, 13, 16, and 17.•SAR of the prepared compounds was discussed.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.130749