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

Girija S. Singh; Yasser M.S.A. Al-Kahraman; Disah Mpadi; Masoom Yasinzai

doi:10.1016/j.bmcl.2012.06.081

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

Girija S. Singh, Yasser M.S.A. Al-Kahraman, Disah Mpadi, Masoom Yasinzai

Chemical & Forensic Sciences

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	5704-5706
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	17
DOIs	https://doi.org/10.1016/j.bmcl.2012.06.081
Publication status	Published - Sep 1 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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title = "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",

abstract = "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.",

author = "Singh, {Girija S.} and Al-Kahraman, {Yasser M.S.A.} and Disah Mpadi and Masoom Yasinzai",

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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. / Singh, Girija S.; Al-Kahraman, Yasser M.S.A.; Mpadi, Disah; Yasinzai, Masoom.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 22, No. 17, 01.09.2012, p. 5704-5706.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

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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

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