Synthesis and SAR study of novel anticancer and antimicrobial naphthoquinone amide derivatives |
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| Affiliation: | 1. Organic Chemistry Division, Central Leather Research Institute (CSIR), Chennai 600 020, India;2. Department of Biotechnology, Indian Institute of Technology Madras, Chennai 600 036, India;3. Biocontrol and Microbial Metabolites Lab, Centre for Advanced Studies in Botany, University of Madras, Maraimalai Campus, Guindy, Chennai 600 025, India;1. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Russian Academy of Sciences, 690022 Vladivostok, Prospect 100 let Vladivostoku 159, Russia;2. School of Natural Sciences, Far East Federal University, 690950 Vladivostok, Sukhanova St. 8, Russia;3. Department of Oncology, Haematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, 20246 Hamburg, Martinistrasse 52, Germany;4. Tumor and Breast Center ZeTuP, 9006 St. Gallen, Rorschacher Strasse 150, Switzerland;1. Department of Biotechnology, Federal University of Paraiba, João Pessoa, Brazil;2. Department of Biochemistry and Pharmacology, Federal University of Piauí, Teresina, Brazil;3. Department of Molecular Sciences, Rural Federal University of Pernambuco, Recife, Brazil;1. Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;2. Department of Pharmacology & Toxicology, National Institute of Pharmaceutical Education& Research, Hyderabad 500037, India;1. Laboratório de Síntese Orgânica & Medicinal, Departamento de Química, Universidade Federal do Espírito Santo, Avenida Ferrari 514, Goiabeiras, Vitória/ES 29075-910, Brazil;2. Laboratório de Petroleômica, Departamento de Química, Universidade Federal do Espírito Santo, Avenida Ferrari 514, Goiabeiras, Vitória/ES 29075-910, Brazil;1. Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039, Assam, India;2. Department of Pharmacology and Pharmaceutical Sciences, School of Pharmacy, University of Southern California, PSC304, 1985 Zonal Avenue, Los Angeles, CA 90089, USA;1. Laboratory of Analysis, Treatment and Valorization of Pollutants of the Environment and Products, Faculty of Pharmacy, Rue Avicenne, Monastir 5000, Tunisia;2. College of Applied Medical Sciences, Medical Laboratory Department, Yanbu el Bahr, Taibah University, Al Madinah Al Monawarah, Saudi Arabia;3. Laboratory of Bacteriology and Molecular Biology, Hôspital of Ibn El Jazzar, Kairouan, Tunisia;4. College of Sciences, Biology Department, Yanbu el Bahr, Taibah University, Al Madinah Al Monawarah, Saudi Arabia |
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| Abstract: | A series of novel naphthoquinone amide derivatives of the bioactive quinones, plumbagin, juglone, menadione and lawsone, with various amino acids were synthesized. The compounds were characterized by 1H NMR, 13C NMR, Mass, IR and elemental analysis. All the compounds were evaluated for their anticancer activity against HeLa and SAS cancer cell lines and 3D-QSAR indicated the presence of electron donating group near sulphur enhanced the activity against HeLa cells. Among the derivatives synthesized, compounds 11f, 10a, 10b and 10g were the most active with IC50 values of 16, 12, 14 and 24.5 μM, respectively. The analogues were also screened for antimicrobial activity against two human bacterial pathogens, the Gram-positive Methicillin resistant Staphylococcus aureus (MRSA) and the Gram-negative Pseudomonas aeruginosa and a human yeast pathogen, Fluconazole resistant Candida albicans (FRCA). Among the synthesized compounds, 8g, 10g and 11g exhibited maximum antibacterial activity towards MRSA and antifungal activity against FRCA in well diffusion method. |
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| Keywords: | Menadione Amide derivatives Anticancer Antimicrobial activity |
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