Cu(OTf)2 catalyzed three component reaction: Efficient synthesis of spiro[indoline-3,4′-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines

K. Parthasarathy; C. Praveen; C. Balachandran; P. Senthil Kumar; S. Ignacimuthu; P. T. Perumal

doi:10.1016/j.bmcl.2013.02.086

Cu(OTf)₂ catalyzed three component reaction: Efficient synthesis of spiro[indoline-3,4′-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines

K. Parthasarathy, C. Praveen, C. Balachandran, P. Senthil Kumar, S. Ignacimuthu, P. T. Perumal

生命医科学研究所

研究成果: Article › 査読

91 被引用数 (Scopus)

抄録

Cu(OTf)₂ catalyzed efficient synthesis of spiropyrano[3,2-b] pyran-4(8H)-ones is accomplished via one-pot three component reaction between isatin, kojic acid and active methylenes. This synthetic protocol is operationally simple and affords product with good to excellent yields at a short reaction time. The synthesized compounds were evaluated for their tumor cell growth inhibitory activity against the human lung cancer cell line (A549) and found that 13 compounds exhibited moderate to good anticancer potency. Molecular docking studies were performed for all the synthesized compounds and the results showed that compound 4e showed greater affinity for anaplastic lymphoma kinase (ALK) receptor.

本文言語	English
ページ（範囲）	2708-2713
ページ数	6
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	23
号	9
DOI	https://doi.org/10.1016/j.bmcl.2013.02.086
出版ステータス	Published - 1 5月 2013

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10.1016/j.bmcl.2013.02.086

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引用スタイル

Parthasarathy, K., Praveen, C., Balachandran, C., Senthil Kumar, P., Ignacimuthu, S., & Perumal, P. T. (2013). Cu(OTf)₂ catalyzed three component reaction: Efficient synthesis of spiro[indoline-3,4′-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines. Bioorganic and Medicinal Chemistry Letters, 23(9), 2708-2713. https://doi.org/10.1016/j.bmcl.2013.02.086

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title = "Cu(OTf)2 catalyzed three component reaction: Efficient synthesis of spiro[indoline-3,4′-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines",

abstract = "Cu(OTf)2 catalyzed efficient synthesis of spiropyrano[3,2-b] pyran-4(8H)-ones is accomplished via one-pot three component reaction between isatin, kojic acid and active methylenes. This synthetic protocol is operationally simple and affords product with good to excellent yields at a short reaction time. The synthesized compounds were evaluated for their tumor cell growth inhibitory activity against the human lung cancer cell line (A549) and found that 13 compounds exhibited moderate to good anticancer potency. Molecular docking studies were performed for all the synthesized compounds and the results showed that compound 4e showed greater affinity for anaplastic lymphoma kinase (ALK) receptor.",

keywords = "A549 lung cancer, Cu(OTf), Molecular docking, Spiro-heterocycles, Three component reaction",

author = "K. Parthasarathy and C. Praveen and C. Balachandran and {Senthil Kumar}, P. and S. Ignacimuthu and Perumal, {P. T.}",

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Parthasarathy, K, Praveen, C, Balachandran, C, Senthil Kumar, P, Ignacimuthu, S & Perumal, PT 2013, 'Cu(OTf)₂ catalyzed three component reaction: Efficient synthesis of spiro[indoline-3,4′-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines', Bioorganic and Medicinal Chemistry Letters, vol. 23, no. 9, pp. 2708-2713. https://doi.org/10.1016/j.bmcl.2013.02.086

Cu(OTf)₂ catalyzed three component reaction: Efficient synthesis of spiro[indoline-3,4′-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines. / Parthasarathy, K.; Praveen, C.; Balachandran, C. その他.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 23, No. 9, 01.05.2013, p. 2708-2713.

研究成果: Article › 査読

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T1 - Cu(OTf)2 catalyzed three component reaction

T2 - Efficient synthesis of spiro[indoline-3,4′-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines

AU - Parthasarathy, K.

AU - Praveen, C.

AU - Balachandran, C.

AU - Senthil Kumar, P.

AU - Ignacimuthu, S.

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AB - Cu(OTf)2 catalyzed efficient synthesis of spiropyrano[3,2-b] pyran-4(8H)-ones is accomplished via one-pot three component reaction between isatin, kojic acid and active methylenes. This synthetic protocol is operationally simple and affords product with good to excellent yields at a short reaction time. The synthesized compounds were evaluated for their tumor cell growth inhibitory activity against the human lung cancer cell line (A549) and found that 13 compounds exhibited moderate to good anticancer potency. Molecular docking studies were performed for all the synthesized compounds and the results showed that compound 4e showed greater affinity for anaplastic lymphoma kinase (ALK) receptor.

KW - A549 lung cancer

KW - Cu(OTf)

KW - Molecular docking

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Parthasarathy K, Praveen C, Balachandran C, Senthil Kumar P, Ignacimuthu S, Perumal PT. Cu(OTf)₂ catalyzed three component reaction: Efficient synthesis of spiro[indoline-3,4′-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines. Bioorganic and Medicinal Chemistry Letters. 2013 5月 1;23(9):2708-2713. doi: 10.1016/j.bmcl.2013.02.086