title: Synthesis and antileishmanial activity of 5-(5-nitroaryl)-2-substituted-thio-1,3,4-thiadiazoles.
abstract: A series of novel 2-substituted-thio-1,3,4-thiadiazoles bearing a 5-nitroaryl moiety including nitrofuran, nitrothiophene or nitroimidazole at the 5-position and a bulky residue attached to the 2-position of the thiadiazole ring were synthesised as potential antileishmanial agents. The target compounds were evaluated against the promastigote form of Leishmania major using the tetrazolium bromide salt (MTT) colorimetric assay. All test compounds exhibited high activity against L. major promastigotes with 50% inhibitory concentrations (IC(50)) ranging from 1.11 to 3.16 μM. The structure-activity relationship study indicated that the S-pendant group attached to the 2-position of the thiadiazole ring has a high flexibility for structural alteration therefore retaining good antileishmanial activity.
authors.affiliation: Department of Chemistry, Islamic Azad University, Tehran-North Branch, Tehran, Iran.
authors.forename: Eskandar
authors.initials: E
authors.lastname: Alipour
authors.forename: Saeed
authors.initials: S
authors.lastname: Emami
authors.forename: Azadeh
authors.initials: A
authors.lastname: Yahya-Meymandi
authors.forename: Maryam
authors.initials: M
authors.lastname: Nakhjiri
authors.forename: Farnaz
authors.initials: F
authors.lastname: Johari
authors.forename: Sussan K
authors.initials: SK
authors.lastname: Ardestani
authors.forename: Fatemeh
authors.initials: F
authors.lastname: Poorrajab
authors.forename: Maryam
authors.initials: M
authors.lastname: Hosseini
authors.forename: Abbas
authors.initials: A
authors.lastname: Shafiee
authors.forename: Alireza
authors.initials: A
authors.lastname: Foroumadi
mesh_terms: D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D018929:Cell Culture Techniques; D006801:Humans; D020128:Inhibitory Concentration 50; D018320:Leishmania major / Q000187:drug effects*; D007896:Leishmaniasis / Q000188:drug therapy / Q000469:parasitology; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013778:Tetrazolium Salts / Q000032:analysis; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D013844:Thiazoles / Q000032:analysis
chemical_list: D000981:Antiprotozoal Agents; D009574:Nitro Compounds; D013778:Tetrazolium Salts; D013830:Thiadiazoles; D013844:Thiazoles; C058949:1,3,4-thiadiazole; C022616:thiazolyl blue