Synthesis and antileishmanial activity of 5-(5-nitroaryl)-2-substituted-thio-1,3,4-thiadiazoles.
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.
Alipour
Eskandar
E
Department of Chemistry, Islamic Azad University, Tehran-North Branch, Tehran, Iran.
Emami
Saeed
S
Yahya-Meymandi
Azadeh
A
Nakhjiri
Maryam
M
Johari
Farnaz
F
Ardestani
Sussan K
SK
Poorrajab
Fatemeh
F
Hosseini
Maryam
M
Shafiee
Abbas
A
Foroumadi
Alireza
A
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
D000981:Antiprotozoal Agents; D009574:Nitro Compounds; D013778:Tetrazolium Salts; D013830:Thiadiazoles; D013844:Thiazoles; C058949:1,3,4-thiadiazole; C022616:thiazolyl blue