Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line

Y. Arun; G. Bhaskar; C. Balachandran; S. Ignacimuthu; P. T. Perumal

doi:10.1016/j.bmcl.2013.01.023

Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line

Y. Arun, G. Bhaskar, C. Balachandran, S. Ignacimuthu, P. T. Perumal

生命医科学研究所

研究成果: Article › 査読

195 被引用数 (Scopus)

抄録

Novel dispirooxindole-pyrrolidine derivatives have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine with the dipolarophile 3-(1H-indol-3-yl)-3-oxo-2-(2-oxoindolin-3- ylidene)propanenitrile, and also spiro compound of acenaphthenequinone obtained by the same optimized reaction condition. Synthesized compounds were evaluated for their antimicrobial activity and all the compounds shown significant activity. Anticancer activity was evaluated against A549 human lung adenocarcinoma cancer cell lines. Compounds 7b, 7g, 7i and 7r exhibit very good anticancer activity 62.96%, 62.03%, 67.67% and 60.22%, respectively, at the dose of 200 μg/mL and compound 7i shows IC₅₀ value in 50 μg/mL.

本文言語	English
ページ（範囲）	1839-1845
ページ数	7
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	23
号	6
DOI	https://doi.org/10.1016/j.bmcl.2013.01.023
出版ステータス	Published - 15 3月 2013

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10.1016/j.bmcl.2013.01.023

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title = "Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line",

abstract = "Novel dispirooxindole-pyrrolidine derivatives have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine with the dipolarophile 3-(1H-indol-3-yl)-3-oxo-2-(2-oxoindolin-3- ylidene)propanenitrile, and also spiro compound of acenaphthenequinone obtained by the same optimized reaction condition. Synthesized compounds were evaluated for their antimicrobial activity and all the compounds shown significant activity. Anticancer activity was evaluated against A549 human lung adenocarcinoma cancer cell lines. Compounds 7b, 7g, 7i and 7r exhibit very good anticancer activity 62.96%, 62.03%, 67.67% and 60.22%, respectively, at the dose of 200 μg/mL and compound 7i shows IC50 value in 50 μg/mL.",

keywords = "Anticancer activity, Antimicrobial activity, Azomethine ylide cycloaddition, Multicomponent reaction, Spirooxindole",

author = "Y. Arun and G. Bhaskar and C. Balachandran and S. Ignacimuthu and Perumal, {P. T.}",

note = "Funding Information: One of the authors Y. Arun thanks the University Grants Commission, New Delhi, India for the research fellowship. ",

year = "2013",

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doi = "10.1016/j.bmcl.2013.01.023",

language = "English",

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}

Arun, Y, Bhaskar, G, Balachandran, C, Ignacimuthu, S & Perumal, PT 2013, 'Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line', Bioorganic and Medicinal Chemistry Letters, vol. 23, no. 6, pp. 1839-1845. https://doi.org/10.1016/j.bmcl.2013.01.023

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AU - Arun, Y.

AU - Bhaskar, G.

AU - Balachandran, C.

AU - Ignacimuthu, S.

AU - Perumal, P. T.

N1 - Funding Information: One of the authors Y. Arun thanks the University Grants Commission, New Delhi, India for the research fellowship.

PY - 2013/3/15

Y1 - 2013/3/15

N2 - Novel dispirooxindole-pyrrolidine derivatives have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine with the dipolarophile 3-(1H-indol-3-yl)-3-oxo-2-(2-oxoindolin-3- ylidene)propanenitrile, and also spiro compound of acenaphthenequinone obtained by the same optimized reaction condition. Synthesized compounds were evaluated for their antimicrobial activity and all the compounds shown significant activity. Anticancer activity was evaluated against A549 human lung adenocarcinoma cancer cell lines. Compounds 7b, 7g, 7i and 7r exhibit very good anticancer activity 62.96%, 62.03%, 67.67% and 60.22%, respectively, at the dose of 200 μg/mL and compound 7i shows IC50 value in 50 μg/mL.

AB - Novel dispirooxindole-pyrrolidine derivatives have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine with the dipolarophile 3-(1H-indol-3-yl)-3-oxo-2-(2-oxoindolin-3- ylidene)propanenitrile, and also spiro compound of acenaphthenequinone obtained by the same optimized reaction condition. Synthesized compounds were evaluated for their antimicrobial activity and all the compounds shown significant activity. Anticancer activity was evaluated against A549 human lung adenocarcinoma cancer cell lines. Compounds 7b, 7g, 7i and 7r exhibit very good anticancer activity 62.96%, 62.03%, 67.67% and 60.22%, respectively, at the dose of 200 μg/mL and compound 7i shows IC50 value in 50 μg/mL.

KW - Anticancer activity

KW - Antimicrobial activity

KW - Azomethine ylide cycloaddition

KW - Multicomponent reaction

KW - Spirooxindole

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