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Synthesis and antileishmanial activity of 5-(5-nitroaryl)-2-substituted-thio-1,3,4-thiadiazoles. 2011

Eskandar Alipour, and Saeed Emami, and Azadeh Yahya-Meymandi, and Maryam Nakhjiri, and Farnaz Johari, and Sussan K Ardestani, and Fatemeh Poorrajab, and Maryam Hosseini, and Abbas Shafiee, and Alireza Foroumadi
Department of Chemistry, Islamic Azad University, Tehran-North Branch, Tehran, Iran.

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.

UI MeSH Term Description Entries
D007896 Leishmaniasis A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL). Leishmania Infection,Infection, Leishmania,Infections, Leishmania,Leishmania Infections,Leishmaniases
D009574 Nitro Compounds Compounds having the nitro group, -NO2, attached to carbon. When attached to nitrogen they are nitramines and attached to oxygen they are NITRATES. Nitrated Compounds
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000981 Antiprotozoal Agents Substances that are destructive to protozoans. Schizonticides,Agents, Antiprotozoal
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013778 Tetrazolium Salts Quaternary salts derived from tetrazoles. They are used in tests to distinguish between reducing sugars and simple aldehydes, for detection of dehydrogenase in tissues, cells, and bacteria, for determination of corticosteroids, and in color photography. (From Mall's Dictionary of Chemistry, 5th ed, p455) Tetrazolium Salt,Salt, Tetrazolium,Salts, Tetrazolium
D013830 Thiadiazoles Heterocyclic compounds composed of a five-membered heterocyclic ring which contains one sulfur and two nitrogen atoms. Thiadiazole
D013844 Thiazoles Heterocyclic compounds where the ring system is composed of three CARBON atoms, a SULFUR and NITROGEN atoms. Thiazole
D018320 Leishmania major A parasitic hemoflagellate of the subgenus Leishmania leishmania that infects man and animals and causes cutaneous leishmaniasis (LEISHMANIASIS, CUTANEOUS) of the Old World. Transmission is by Phlebotomus sandflies. Leishmania (Leishmania) major,Leishmania tropica major,Leishmania leishmania major,Leishmania leishmania majors,Leishmania majors,Leishmania tropica majors,leishmania major, Leishmania,major, Leishmania leishmania,majors, Leishmania,majors, Leishmania leishmania,majors, Leishmania tropica,tropica major, Leishmania,tropica majors, Leishmania
D018929 Cell Culture Techniques Methods for maintaining or growing CELLS in vitro. Cell Culture,Cell Culture Technique,Cell Cultures,Culture Technique, Cell,Culture Techniques, Cell

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