l-like 3-deazaneplanocin analogues: Synthesis and antiviral properties |
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| Institution: | 1. Department of Chemistry, Dr. Babasaheb Ambedkar, Marathwada University, Aurangabad 431 004, Maharashtra, India;2. Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431 004, Maharashtra, India;3. Department of Pharmaceutical Chemistry, R.C. Patel Institute of Pharmaceutical Education & Research, Shirpur 425 405, Maharashtra, India;4. Department of Pharmaceutical Chemistry, Durgamata Institute of Pharmacy, Dharmapuri, Parbhani 431 401, Maharashtra, India;5. Department of Animal Biology, University of Hyderabad, Hyderabad 500 046, India;1. College of Pharmaceutical Sciences, Soochow University, Suzhou 215123, China;2. State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China;3. School of Pharmacy, Guizhou Medical University, Guiyang 550025, China;4. Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guiyang 550004, China;5. The 940th Hospital of Joint Logistics Support Force, Lanzhou 730050, China;1. Anticancer Agent Research Center, KRIBB, Cheongju 28116, Republic of Korea;2. Department of Bioengineering, Hanyang University, Seoul 04763, Republic of Korea;3. Department of Chemistry, Chonnam National University, Gwangju 61186, Republic of Korea;4. Department of Bioscience and Biotechnology, Sejong University, Seoul 05006, Republic of Korea;1. Laboratory of Analytical Chemistry, Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan;2. School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women''s University, 11-68 Koshien-Kyubancho, Nishinomiya, Hyogo 663-8179, Japan;3. Laboratory of Synthetic Medicinal Chemistry, Graduate School of Pharmaceutical Sciences, Osaka University, Yamadaoka 1-6, Suita, Osaka 565-0871, Japan;4. Compound Library Screening Center, Graduate School of Pharmaceutical Sciences, Osaka University, Yamadaoka 1-6, Suita, Osaka 565-0871, Japan;1. Centre for Fluoro-Agrochemicals, CSIR-Indian Institute of Chemical Technology, Tarnaka, 500007 Hyderabad, India;2. Academy of Scientific and Innovative Research, Ghaziabad 201002, India;3. Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India;4. Stem Cell Research Division, National Institute of Nutrition (NIN), Indian Council of Medical Research (ICMR), Hyderabad 500007, Telangana, India;5. School of Pharmaceutical Education and Research (SPER), Jamia Hamdard, New Delhi 110062, India;1. Centro de Ciências Naturais e Humanas, Universidade Federal do ABC, Santo André, SP 09210-580, Brazil;2. Departamento de Química, Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Diadema, SP 09972-270, Brazil;3. Instituto de Química, Universidade de Brasília, Brasília, DF 70910-900, Brazil;4. Centro de Parasitologia e Micologia, Instituto Adolfo Lutz, São Paulo, SP 01246-000, Brazil |
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| Abstract: | The potent antiviral properties of 3-deazaneplanocin, 3-deaza-isoneplanocins (1) and recently discovered l-like carbocyclic nucleosides (2, 3 and 4) prompted us to pursue rationally conceived l-like 3-deazaneplanocin analogues. The synthesis of those analogues including l-like 3-deazaneplanocin (5), l-like 3-bromo-3-deazaneplanocin (6), and l-like 5′-fluoro-5′-deoxy-3-deazaneplanocin (7), was accomplished from a common intermediate, (?)-cyclopentenone (8). Antiviral analysis found 5 and 6 to display favorable activity against the Ebola virus, as expected for 3-deazaadenine carbocyclic nucleosides. Compound 5 also showed activity against arenaviruses, including Pinchinde and Tacaribe. |
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| Keywords: | Carbocyclic nucleosides 3-Deazaneplanocin Antiviral Anti-Ebola |
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