title: Synthesis, spectral characterization, molecular structure and pharmacological studies of N'-(1, 4-naphtho-quinone-2yl) isonicotinohydrazide.
abstract: A simple and efficient procedure was employed for the synthesis of N'-(1,4-naphtho-quinone-2-yl) isonicotinohydrazide (NIH) by the reaction of 2-hydroxy-1,4-naphthaquinone (lawsone) and isonicotinoyl hydrazine in methanol using ultrasonic irradiation. Lawsone is the principal dye, isolated from the leaves of henna (Lawsonia inermis). Structural modification was done on the molecule aiming to get a more active derivative. The structure of the parent compound and the derivative was characterized by elemental analyses, infrared, electronic, (1)H, (13)C NMR and GC-MS spectra. The fluorescence spectral investigation of the compound was studied in DMSO and ethanol. Single crystal X-ray diffraction studies reveal that NIH crystallizes in monoclinic space group. The DNA cleavage study was monitored by gel electrophoresis method. The synthesized compound was found to have significant antioxidant activity against DPPH radical (IC50=58 μM). The in vitro cytotoxic studies of the derivative against two human cancer cell lines MCF-7 (human breast cancer) and HCT-15 (human colon carcinoma cells) using MTT assay revealed that the compound exhibited higher cytotoxic activity with a lower IC50 value indicating its efficiency in killing the cancer cells even at low concentrations. These results suggest that the structural modifications performed on lawsone could be considered a good strategy to obtain a more active drug.
authors.affiliation: Dept. of Chemistry, Govt. College for Women, Thiruvananthapuram 695014, Kerala, India. Electronic address: raghavkavitha@gmail.com.
authors.forename: P R
authors.initials: PR
authors.lastname: Kavitha Rani
authors.affiliation: Dept. of Chemistry, College of Engineering, Trivandrum (CET) 695016, Kerala, India.
authors.forename: Annette
authors.initials: A
authors.lastname: Fernandez
authors.affiliation: Dept. of Chemistry, Govt. College for Women, Thiruvananthapuram 695014, Kerala, India.
authors.forename: Annie
authors.initials: A
authors.lastname: George
authors.affiliation: Dept. of Chemistry, Govt. College for Women, Thiruvananthapuram 695014, Kerala, India.
authors.forename: V K
authors.initials: VK
authors.lastname: Remadevi
authors.affiliation: Dept. of Chemistry, Mahatma Gandhi College, Thiruvananthapuram 695004, Kerala, India.
authors.forename: M R
authors.initials: MR
authors.lastname: Sudarsanakumar
authors.affiliation: Dept. of Chemistry, College of Engineering, Trivandrum (CET) 695016, Kerala, India.
authors.forename: Shiny P
authors.initials: SP
authors.lastname: Laila
authors.affiliation: Govt. Arts College, Thiruvananthapuram 695014, Kerala, India.
authors.forename: Muhammed
authors.initials: M
authors.lastname: Arif
mesh_terms: D001205:Ascorbic Acid / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D053837:DNA Cleavage / Q000187:drug effects; D004587:Electrophoresis, Agar Gel; D016166:Free Radical Scavengers / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D006860:Hydrogen Bonding; D007538:Isoniazid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008968:Molecular Conformation; D010851:Picrates / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D012015:Reference Standards; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D006834:Hydrazines; C000598857:N'-(1, 4-naphtho-quinone-2yl)isonicotinohydrazide; D010851:Picrates; C029424:hydrazine; C004931:1,1-diphenyl-2-picrylhydrazyl; D001205:Ascorbic Acid; D007538:Isoniazid
keywords: Isonicotinoyl hydrazine and MTT assay; Lawsone; Ultrasound irradiation