New 5-(nitroheteroaryl)-1,3,4-thiadiazols containing acyclic amines at C-2: synthesis and SAR study for their antileishmanial activity.
A novel series of 5-(5-nitrofuran-2-yl)-and 5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazole-2-amines bearing acyclic amine at C-2 position of thiadiazole ring were synthesized and evaluated in vitro against promastigote and amastigote forms of Leishmania major. The structure-activity of series was investigated by studying 40 compounds. The most active derivatives were hydroxypropylamino- and methoxypropylamino- analogs of 5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazole (compounds 29 and 32, respectively) with highest selectivity index (SI >12).
Department of Medicinal Chemistry, School of Pharmacy and Biotechnology Research Center, Tabriz University of Medical Sciences, Tabriz, Iran.
Azar
A
Tahghighi
Saeed
S
Emami
Sepide
S
Razmi
Farzane
F
Rezazade Marznaki
Sussan
S
Kabudanian Ardestani
Siavoush
S
Dastmalchi
Farzad
F
Kobarfard
Abbas
A
Shafiee
Alireza
A
Foroumadi
D000588:Amines / Q000737:chemistry*; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D018320:Leishmania major / Q000187:drug effects*; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013830:Thiadiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
D000588:Amines; D000981:Antiprotozoal Agents; D013830:Thiadiazoles; C058949:1,3,4-thiadiazole