title: Synthesis and multi-spectroscopic DNA binding study of 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives of fatty acid.
abstract: A facile and convenient synthesis of a series of fatty acid derivatives of 1,3,4-oxadiazole and 1,3,4-thiadiazole has been described. The key step of this protocol is the cyclization of acyl thiosemicarbazides via iodobenzene diacetate and methanesulfonic acid under mild conditions. The newly synthesized compounds were characterized by FT-IR, (1)HNMR, (13)CNMR and mass spectral study. The binding affinity of 5-(pentadecyl)-N-propenyl-1,3,4-oxadiazol-2-amine (3a) and 5-(heptadecyl)-2-amino-1,3,4-thiadiazole (6a) with CT-DNA has been evaluated by UV, fluorescence, Circular Dichroism (CD) and thermal denaturation studies. It has been found that these small and planer heteroaromatic compounds are capable of binding to the minor groove region of DNA.
authors.affiliation: Department of Chemistry, Aligarh Muslim University, Aligarh 202002, Uttar Pradesh, India.
authors.forename: Mohammad F
authors.initials: MF
authors.lastname: Hassan
authors.affiliation: Department of Chemistry, Aligarh Muslim University, Aligarh 202002, Uttar Pradesh, India. Electronic address: abduloafchem@gmail.com.
authors.forename: Abdul
authors.initials: A
authors.lastname: Rauf
mesh_terms: D000818:Animals; D002417:Cattle; D002942:Circular Dichroism; D003500:Cyclization; D004247:DNA / Q000378:metabolism*; D004583:Electrons; D004996:Ethidium / Q000737:chemistry; D005227:Fatty Acids / Q000378:metabolism*; D007462:Iodobenzenes / Q000737:chemistry; D062105:Molecular Docking Simulation; D009691:Nucleic Acid Denaturation; D010069:Oxadiazoles / Q000378:metabolism*; D066244:Proton Magnetic Resonance Spectroscopy; D012997:Solvents; D013050:Spectrometry, Fluorescence; D017550:Spectroscopy, Fourier Transform Infrared; D013696:Temperature; D013830:Thiadiazoles / Q000378:metabolism*
chemical_list: D005227:Fatty Acids; D007462:Iodobenzenes; D010069:Oxadiazoles; D012997:Solvents; D013830:Thiadiazoles; C058949:1,3,4-thiadiazole; C583463:1,3,4-oxadiazole; D004247:DNA; C427203:calf thymus DNA; C031905:iodobenzene; D004996:Ethidium
keywords: 1,3,4-Oxadiazole; 1,3,4-Thiadiazole; CT-DNA binding; Spectral studies