Facile synthesis of antimalarial 1,2-disubstituted 4-quinolones from 1,3-bisaryl-monothio-1,3-diketones

Ajjampura C. Vinayaka; Maralinganadoddi P. Sadashiva; Xianzhu Wu; Sergei S. Biryukov; José A. Stoute; Kanchugarakoppal S. Rangappa; D. Channe Gowda

doi:10.1039/c4ob01455c

Facile synthesis of antimalarial 1,2-disubstituted 4-quinolones from 1,3-bisaryl-monothio-1,3-diketones

Ajjampura C. Vinayaka, Maralinganadoddi P. Sadashiva, Xianzhu Wu, Sergei S. Biryukov, José A. Stoute, Kanchugarakoppal S. Rangappa, D. Channe Gowda

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27 Scopus citations

Abstract

A new strategy was developed to synthesize 1,2-disubstituted 4-quinolones in good yield starting from 1,3-bisaryl-monothio-1,3-diketone substrates. The synthesized compounds were evaluated for antimalarial activity using Plasmodium falciparum strains. All compounds, except for two, showed good activity. Of these, seven compounds exhibited an excellent antimalarial activity (IC₅₀, <2 μM). More importantly, all seven compounds were equally effective in inhibiting the growth of both chloroquine-sensitive and chloroquine-resistant strains. The cytotoxicity assessment using carcinoma and non-carcinoma human cell lines revealed that almost all synthesized compounds were minimally cytotoxic (IC₅₀, >50 μM). This journal is

Original language	English (US)
Pages (from-to)	8555-8561
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	42
DOIs	https://doi.org/10.1039/c4ob01455c
State	Published - Nov 14 2014

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Facile synthesis of antimalarial 1,2-disubstituted 4-quinolones from 1,3-bisaryl-monothio-1,3-diketones",

abstract = "A new strategy was developed to synthesize 1,2-disubstituted 4-quinolones in good yield starting from 1,3-bisaryl-monothio-1,3-diketone substrates. The synthesized compounds were evaluated for antimalarial activity using Plasmodium falciparum strains. All compounds, except for two, showed good activity. Of these, seven compounds exhibited an excellent antimalarial activity (IC50, <2 μM). More importantly, all seven compounds were equally effective in inhibiting the growth of both chloroquine-sensitive and chloroquine-resistant strains. The cytotoxicity assessment using carcinoma and non-carcinoma human cell lines revealed that almost all synthesized compounds were minimally cytotoxic (IC50, >50 μM). This journal is",

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doi = "10.1039/c4ob01455c",

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AU - Vinayaka, Ajjampura C.

AU - Sadashiva, Maralinganadoddi P.

AU - Wu, Xianzhu

AU - Biryukov, Sergei S.

AU - Stoute, José A.

AU - Rangappa, Kanchugarakoppal S.

AU - Gowda, D. Channe

N1 - Publisher Copyright: © the Partner Organisations 2014.

PY - 2014/11/14

Y1 - 2014/11/14

N2 - A new strategy was developed to synthesize 1,2-disubstituted 4-quinolones in good yield starting from 1,3-bisaryl-monothio-1,3-diketone substrates. The synthesized compounds were evaluated for antimalarial activity using Plasmodium falciparum strains. All compounds, except for two, showed good activity. Of these, seven compounds exhibited an excellent antimalarial activity (IC50, <2 μM). More importantly, all seven compounds were equally effective in inhibiting the growth of both chloroquine-sensitive and chloroquine-resistant strains. The cytotoxicity assessment using carcinoma and non-carcinoma human cell lines revealed that almost all synthesized compounds were minimally cytotoxic (IC50, >50 μM). This journal is

AB - A new strategy was developed to synthesize 1,2-disubstituted 4-quinolones in good yield starting from 1,3-bisaryl-monothio-1,3-diketone substrates. The synthesized compounds were evaluated for antimalarial activity using Plasmodium falciparum strains. All compounds, except for two, showed good activity. Of these, seven compounds exhibited an excellent antimalarial activity (IC50, <2 μM). More importantly, all seven compounds were equally effective in inhibiting the growth of both chloroquine-sensitive and chloroquine-resistant strains. The cytotoxicity assessment using carcinoma and non-carcinoma human cell lines revealed that almost all synthesized compounds were minimally cytotoxic (IC50, >50 μM). This journal is

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Facile synthesis of antimalarial 1,2-disubstituted 4-quinolones from 1,3-bisaryl-monothio-1,3-diketones

Abstract

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