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Synthesis of N-(1-methyl-1H-indol-3-yl)methyleneamines and 3,3-diaryl-4-(1-methyl-1H-indol-3-yl)azetidin-2-ones as potential antileishmanial agents. 2012

Girija S Singh, and Yasser M S A Al-Kahraman, and Disah Mpadi, and Masoom Yasinzai
Chemistry Department, University of Botswana, Private Bag: 0022, Gaborone, Botswana. singhgs@mopipi.ub.bw

A series of N-(1-methyl-1H-indol-3-yl)methyleneamines and eight new 3,3-diaryl-4-(1-methyl-1H-indol-3-yl)azetidin-2-ones have been synthesized and screened for their antileishmanial activity against Leishmania major. 3,3-Diaryl-4-(1-methyl-1H-indol-3-yl)azetidin-2-ones have been synthesized by the Staudinger's ketene-imine cycloaddition employing two 2-diazo-1,2-diarylethanones as the precursors of diarylketenes. A marked improvement in anti-parasitic activity is observed by transformation of the methyleneamines to azetidin-2-ones in seven out of eight compounds. Two compounds displayed antileishmanial activity comparable to that of the clinically used antileshmanial drug, amphotericine B.

UI MeSH Term Description Entries
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
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
D001384 Azetidines
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
D016773 Leishmaniasis, Cutaneous An endemic disease that is characterized by the development of single or multiple localized lesions on exposed areas of skin that typically ulcerate. The disease has been divided into Old and New World forms. Old World leishmaniasis is separated into three distinct types according to epidemiology and clinical manifestations and is caused by species of the L. tropica and L. aethiopica complexes as well as by species of the L. major genus. New World leishmaniasis, also called American leishmaniasis, occurs in South and Central America and is caused by species of the L. mexicana or L. braziliensis complexes. Leishmaniasis, American,Leishmaniasis, New World,Leishmaniasis, Old World,Oriental Sore,American Leishmaniasis,Cutaneous Leishmaniases,Cutaneous Leishmaniasis,Leishmaniases, Cutaneous,New World Leishmaniasis,Old World Leishmaniasis,Sore, Oriental
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

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