Synthesis,characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors |
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| Institution: | 1. Institute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden, 11800 Penang, Malaysia;2. New Drug Discovery Research, Department of Medicinal Chemistry, Alwar Pharmacy College, Alwar, Rajasthan 301 030, India;3. New Drug Discovery Research, Department of Medicinal Chemistry, Sunrise University, Alwar, Rajasthan 301 030, India;4. Department of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Minden, 11800 Penang, Malaysia;5. Department of Organic Chemistry, School of Chemical Sciences, Universiti Sains Malaysia, Minden, 11800 Penang, Malaysia;6. Department of Chemistry, Vidya Bharati College, Amravati, Maharashtra 444 602, India;1. Department of Pharmaceutical Engineering, School of Biological Science and Technology, University of Jinan, Jinan 250022, China;2. Institute of Biological Sciences, University of Brasília, Brasilia 70910900, Brazil;3. College of Pharmacy, Weifang Medical University, Weifang 261042, China;4. Faculty of Ceilandia, University of Brasilia, Brasilia 72220-900, Brazil;1. Department of Pharmaceutical Sciences, ASBASJSM College of Pharmacy, Bela, Ropar, Punjab, India;2. Drug Discovery Research, Panacea Biotec Pvt. Ltd., Mohali, Punjab, India;3. Rayat-Bahra Institute of Pharmacy, Hoshiarpur, Punjab, India;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University), New Delhi 110062, India;2. College of Pharmacy and Dentistry, Buraydah Private Colleges, Al-Qassim 31717, Saudi Arabia;3. School of Computational & Integrative Sciences, Jawaharlal Nehru University, New Delhi 110067, India;4. Department of Medicinal Chemistry, Maharishi Arvind College of Pharmacy Jaipur, Rajasthan 301 039, India;5. College of Clinical Pharmacy, University of Dammam, Dammam 31441, Saudi Arabia;6. Department of Pharmaceutical Sciences & Technology, Birla Institute of Technology, Mesra, Ranchi, Jharkhand 835 215, India;7. Department of Toxicology, Faculty of Science, Jamia Hamdard (Hamdard University), New Delhi 110062, India;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, El-Kasr El-Eini Street, P.O. Box 11562, Cairo, Egypt;2. Department of Chemistry, Agri Ibrahim Cecen University, Faculty of Science and Arts, 04100 Agri, Turkey;3. Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey;1. Pharmacy Faculty, Tabriz University of Medical Sciences, Tabriz, Iran;2. Organic Chemistry and Phytochemistry Research Laboratory, Faculty of Sciences, Azarbaijan Shahid Madani University, Tabriz, Iran;3. Research Center for Pharmaceutical Nanotechnology, Tabriz University of Medical Sciences, Tabriz, Iran;4. Drug Applied Research Center and Pharmacy Faculty, Tabriz University of Medical Sciences, Tabriz, Iran;5. Department of Plant Production and Breeding Engineering, Faculty of Engineering and Technology, Imam Khomeini International University, Qazvin, Iran;1. Department of Chemistry, Faculty of Art and Sciences, Recep Tayyip Erdogan University, 53100 Rize, Turkey;2. Vocational School of Technical Studies, Department of Chemistry and Chemical Processing Technology, Recep Tayyip Erdogan University, 53100 Rize, Turkey;3. Department of Nutrition and Dietetics, Faculty of Health Sciences, Karadeniz Technical University, 61080 Trabzon, Turkey |
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| Abstract: | Two series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structure were synthesized by a four-step reaction pathway starting from 4-fluoro-3-nitrobenzoic acid as the basic compound. The structure of the novel benzimidazoles was characterized and confirmed by the elemental and mass spectral analyses as well as 1H NMR spectroscopic data. Of the 34 novel synthesized compounds, three benzimidazoles revealed AChE inhibition with IC50 < 10 μM. The highest inhibitory activity (IC50 = 5.12 μM for AChE and IC50 = 8.63 μM for BChE) corresponds to the compound 5IIc (ethyl 1-(3-(1H-imidazol-1-yl)propyl)-2-(4-nitrophenyl)-1H-benzod]imidazole-5-carboxylate). The relationship between lipophilicity and the chemical structures as well as their limited structure–activity relationship was discussed. |
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| Keywords: | Benzimidazoles Acetylcholinesterase Butyrylcholinesterase Alzheimer’s Disease |
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