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-dichloropyrrolo[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 CI or CH3 on C2 position. (C) 2019 Elsevier Ltd. All rights reserved.