Novel pyrrolo[2,3-d]pyrimidine derivatives: Design,synthesis, structure elucidation and in vitro anti-BVDV activity |
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| Institution: | 1. Organometallic and Organometalloid Chemistry Department, National Research Centre, 12622 Cairo, Egypt;2. Microbial Biotechnology Department, National Research Centre, Cairo, Egypt;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy (girls), Al-Azhar University, Nasr City, Cairo, Egypt;2. Department of Organic Chemistry, Faculty of Science, Ain Shams University, Abbassia, 11566 Cairo, Egypt;1. School of Chemical Engineering, Guizhou Institute of Technology, Guiyang 550003, China;2. Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China;3. Drug identification Center of Guiyang Municipal Public Security Bureau, Guiyang Municipal Public Security Bureau, Guiyang 550081, China;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, Kasr El-Aini Street, Cairo 11562, Egypt;2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, MSA University, 6th October City, Cairo, Egypt;1. School of Pharmacy, Fudan University, Shanghai, 201203, PR China;2. Novel Technology Center of Pharmaceutical Chemistry, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, 285 Gebaini Road, Shanghai, 201203, PR China;3. WuXi AppTec, 288 Fute Zhong Road, Waigaoqiao Free Trade Zone, Shanghai, 200131, PR China;1. Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan 250012, Shandong, PR China;2. Department of Lymphoma and Myeloma, The University of Texas MD Anderson Cancer Center, Houston, TX 77030, USA;3. School of Pharmacy and Jiangsu Province Key Laboratory for Inflammation and Molecular Drug Target, Nantong University, Nantong 226001, PR China;1. Dipartimento di Farmacia, Università degli Studi di Genova, Viale Benedetto XV, 3, 16132 Genova, Italy;2. Dipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Via Aldo Moro 2, 53100 Siena, Italy;3. Dipartimento di Farmacia, Università“Federico II” di Napoli, Via D. Montesano 49, 80131 Napoli, Italy;4. Consiglio Nazionale delle Ricerche, Istituto di Fisiologia Clinica and Istituto Toscano Tumori, Core Research Laboratory, Via Fiorentina 1, 53100 Siena, Italy;5. Consiglio Nazionale delle Ricerche, Istituto di Genetica Molecolare, IGM-CNR, Via Abbiategrasso 207, 27100 Pavia, Italy |
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| Abstract: | 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-pyrrolo2,3-d]pyrimidine 10 elucidated by single crystal X-ray diffraction. Herein, we reported the first pyrrolo2,3-d]pyrimidine compounds with trichloromethane at position 2 of the pyrimidine ring. As initial biological activity screening, evaluation of the pyrrolo2,3-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 pyrrolo2,3-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. |
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| Keywords: | 4 6-Dichloro-pyrrolo[2 3-d]pyrimidine 2-Trichloromethylpyrrolopyrimidines Anti-BVDV SAR |
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