title: Synthesis and anti-leishmanial activity of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines containing N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] moieties.
abstract: A novel series of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines were synthesized by introducing N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] moiety as a new functionality on the C-2 amine of thiadiazole ring via click chemistry. The title compounds namely, N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amines (3a-n) were characterized by IR, NMR and MS spectra. These compounds were evaluated for their in vitro anti-leishmanial activity against promostigote form of the Leishmania major. Most compounds exhibited good anti-leishmanial activity against the promastigote form of L. major. The most active compound against promostigotes was found to be 4-methylbenzyl analog 3i, which significantly decreases the number of intracellular amastigotes per macrophage, percentage of macrophage infectivity and infectivity index.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran.
authors.forename: Azar
authors.initials: A
authors.lastname: Tahghighi
authors.forename: Sepideh
authors.initials: S
authors.lastname: Razmi
authors.forename: Mohammad
authors.initials: M
authors.lastname: Mahdavi
authors.forename: Parham
authors.initials: P
authors.lastname: Foroumadi
authors.forename: Sussan K
authors.initials: SK
authors.lastname: Ardestani
authors.forename: Saeed
authors.initials: S
authors.lastname: Emami
authors.forename: Farzad
authors.initials: F
authors.lastname: Kobarfard
authors.forename: Siavoush
authors.initials: S
authors.lastname: Dastmalchi
authors.forename: Abbas
authors.initials: A
authors.lastname: Shafiee
authors.forename: Alireza
authors.initials: A
authors.lastname: Foroumadi
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002478:Cells, Cultured; D018320:Leishmania major / Q000187:drug effects*; D007896:Leishmaniasis / Q000188:drug therapy*; D017737:Macrophages, Peritoneal / Q000187:drug effects* / Q000469:parasitology; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000981:Antiprotozoal Agents; C573624:N-((1-(4-methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-amine; D013830:Thiadiazoles; D014230:Triazoles