Novel spirooxindole-pyrrolidine compounds: Synthesis, anticancer and molecular docking studies

Y. Arun; K. Saranraj; C. Balachandran; P. T. Perumal

doi:10.1016/j.ejmech.2013.12.027

Novel spirooxindole-pyrrolidine compounds: Synthesis, anticancer and molecular docking studies

Y. Arun, K. Saranraj, C. Balachandran, P. T. Perumal

生命医科学研究所

研究成果: Article › 査読

135 被引用数 (Scopus)

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Novel spirooxindole-pyrrolidine compounds have been synthesised through 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or thioproline with the dipolarophile 3-(1H-imidazol-2-yl)-2-(1H- indole-3-carbonyl)acrylonitrile under the optimised reaction condition. Synthesised compounds were evaluated for their anticancer activity against A549 human lung adenocarcinoma cancer cell line. Among the 29 tested compounds 4j, 6b and 6h showed very high activity 66.3%, 64.8% and 66.3% at 25 μg/mL concentration against A549 lung adenocarcinoma cancer cell line. These spirooxindole-pyrrolidine compounds can be promising therapeutic agents for A549 lung adenocarcinoma cancer cell line.

本文言語	English
ページ（範囲）	50-64
ページ数	15
ジャーナル	European Journal of Medicinal Chemistry
巻	74
DOI	https://doi.org/10.1016/j.ejmech.2013.12.027
出版ステータス	Published - 3 3月 2014

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title = "Novel spirooxindole-pyrrolidine compounds: Synthesis, anticancer and molecular docking studies",

abstract = "Novel spirooxindole-pyrrolidine compounds have been synthesised through 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or thioproline with the dipolarophile 3-(1H-imidazol-2-yl)-2-(1H- indole-3-carbonyl)acrylonitrile under the optimised reaction condition. Synthesised compounds were evaluated for their anticancer activity against A549 human lung adenocarcinoma cancer cell line. Among the 29 tested compounds 4j, 6b and 6h showed very high activity 66.3%, 64.8% and 66.3% at 25 μg/mL concentration against A549 lung adenocarcinoma cancer cell line. These spirooxindole-pyrrolidine compounds can be promising therapeutic agents for A549 lung adenocarcinoma cancer cell line.",

keywords = "Anticancer activity, Azomethine ylide cycloaddition, Molecular docking, Multicomponent reaction, Pyrrolidine, Spirooxindole",

author = "Y. Arun and K. Saranraj and C. Balachandran 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 = "2014",

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doi = "10.1016/j.ejmech.2013.12.027",

language = "English",

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T2 - Synthesis, anticancer and molecular docking studies

AU - Arun, Y.

AU - Saranraj, K.

AU - Balachandran, C.

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 - 2014/3/3

Y1 - 2014/3/3

N2 - Novel spirooxindole-pyrrolidine compounds have been synthesised through 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or thioproline with the dipolarophile 3-(1H-imidazol-2-yl)-2-(1H- indole-3-carbonyl)acrylonitrile under the optimised reaction condition. Synthesised compounds were evaluated for their anticancer activity against A549 human lung adenocarcinoma cancer cell line. Among the 29 tested compounds 4j, 6b and 6h showed very high activity 66.3%, 64.8% and 66.3% at 25 μg/mL concentration against A549 lung adenocarcinoma cancer cell line. These spirooxindole-pyrrolidine compounds can be promising therapeutic agents for A549 lung adenocarcinoma cancer cell line.

AB - Novel spirooxindole-pyrrolidine compounds have been synthesised through 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or thioproline with the dipolarophile 3-(1H-imidazol-2-yl)-2-(1H- indole-3-carbonyl)acrylonitrile under the optimised reaction condition. Synthesised compounds were evaluated for their anticancer activity against A549 human lung adenocarcinoma cancer cell line. Among the 29 tested compounds 4j, 6b and 6h showed very high activity 66.3%, 64.8% and 66.3% at 25 μg/mL concentration against A549 lung adenocarcinoma cancer cell line. These spirooxindole-pyrrolidine compounds can be promising therapeutic agents for A549 lung adenocarcinoma cancer cell line.

KW - Anticancer activity

KW - Azomethine ylide cycloaddition

KW - Molecular docking

KW - Multicomponent reaction

KW - Pyrrolidine

KW - Spirooxindole

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SN - 0223-5234

VL - 74

SP - 50

EP - 64

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

Novel spirooxindole-pyrrolidine compounds: Synthesis, anticancer and molecular docking studies

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