title: Synthesis and SAR study of novel anticancer and antimicrobial naphthoquinone amide derivatives.
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 (1)H NMR, (13)C 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.
authors.affiliation: Organic Chemistry Division, Central Leather Research Institute (CSIR), Chennai 600 020, India. Electronic address: t_sree_latha@yahoo.com.
authors.forename: Thonthula
authors.initials: T
authors.lastname: Sreelatha
authors.affiliation: Organic Chemistry Division, Central Leather Research Institute (CSIR), Chennai 600 020, India.
authors.forename: Subramani
authors.initials: S
authors.lastname: Kandhasamy
authors.affiliation: Department of Biotechnology, Indian Institute of Technology Madras, Chennai 600 036, India.
authors.forename: Raghu
authors.initials: R
authors.lastname: Dinesh
authors.affiliation: Department of Biotechnology, Indian Institute of Technology Madras, Chennai 600 036, India.
authors.forename: Suresh
authors.initials: S
authors.lastname: Shruthy
authors.affiliation: Department of Biotechnology, Indian Institute of Technology Madras, Chennai 600 036, India.
authors.forename: Sinha
authors.initials: S
authors.lastname: Shweta
authors.affiliation: Department of Biotechnology, Indian Institute of Technology Madras, Chennai 600 036, India.
authors.forename: Doble
authors.initials: D
authors.lastname: Mukesh
authors.affiliation: Department of Biotechnology, Indian Institute of Technology Madras, Chennai 600 036, India.
authors.forename: Devarajan
authors.initials: D
authors.lastname: Karunagaran
authors.affiliation: Biocontrol and Microbial Metabolites Lab, Centre for Advanced Studies in Botany, University of Madras, Maraimalai Campus, Guindy, Chennai 600 025, India.
authors.forename: Ravichandran
authors.initials: R
authors.lastname: Balaji
authors.affiliation: Biocontrol and Microbial Metabolites Lab, Centre for Advanced Studies in Botany, University of Madras, Maraimalai Campus, Guindy, Chennai 600 025, India.
authors.forename: Narayanasamy
authors.initials: N
authors.lastname: Mathivanan
authors.affiliation: Organic Chemistry Division, Central Leather Research Institute (CSIR), Chennai 600 020, India.
authors.forename: Paramasivan Thirumalai
authors.initials: PT
authors.lastname: Perumal
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D025141:Drug Resistance, Fungal / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D015725:Fluconazole / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011550:Pseudomonas aeruginosa / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D015725:Fluconazole
keywords: Amide derivatives; Anticancer; Antimicrobial activity; Juglans regia; Lawsonia inermis; Menadione; Plumbago zeylanica