Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles: a faster access to spirooxindoles of potential pharmacological interest

Shambhu Nath Singh; Sridhar Regati; Abir Kumar Paul; Mohosin Layek; Sarva Jayaprakash; K. Venkateshwara Reddy; Girdhar Singh Deora; Soumita Mukherjee; Manojit Pal

doi:10.1016/j.tetlet.2013.07.126

Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles: a faster access to spirooxindoles of potential pharmacological interest

Shambhu Nath Singh, Sridhar Regati, Abir Kumar Paul, Mohosin Layek, Sarva Jayaprakash, K. Venkateshwara Reddy, Girdhar Singh Deora, Soumita Mukherjee, Manojit Pal

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

36 Citations (Scopus)

Abstract

CuI facilitated three-component reaction of isatin derivatives, l-proline and terminal alkynes containing an amide or ester functional group. The multi-component reaction (MCR) afforded a faster and practical synthesis of spirooxindole derivatives. A range of novel spirooxindoles were synthesized by using this straightforward and one-pot efficient methodology. A representative compound showed significant inhibition of PDE4B enzyme in vitro and good interactions with this protein in silico.

Original language	English
Pages (from-to)	5448-5452
Number of pages	5
Journal	Tetrahedron Letters
Volume	54
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2013.07.126
Publication status	Published - 2 Oct 2013
Externally published	Yes

Keywords

CuI
MCR
PDE4B
Spirooxindole

Access to Document

10.1016/j.tetlet.2013.07.126

Link to publication in Scopus

Cite this

Singh, S. N., Regati, S., Paul, A. K., Layek, M., Jayaprakash, S., Reddy, K. V., Deora, G. S., Mukherjee, S., & Pal, M. (2013). Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles: a faster access to spirooxindoles of potential pharmacological interest. Tetrahedron Letters, 54(40), 5448-5452. https://doi.org/10.1016/j.tetlet.2013.07.126

Singh, Shambhu Nath ; Regati, Sridhar ; Paul, Abir Kumar ; Layek, Mohosin ; Jayaprakash, Sarva ; Reddy, K. Venkateshwara ; Deora, Girdhar Singh ; Mukherjee, Soumita ; Pal, Manojit. / Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles : a faster access to spirooxindoles of potential pharmacological interest. In: Tetrahedron Letters. 2013 ; Vol. 54, No. 40. pp. 5448-5452.

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abstract = "CuI facilitated three-component reaction of isatin derivatives, l-proline and terminal alkynes containing an amide or ester functional group. The multi-component reaction (MCR) afforded a faster and practical synthesis of spirooxindole derivatives. A range of novel spirooxindoles were synthesized by using this straightforward and one-pot efficient methodology. A representative compound showed significant inhibition of PDE4B enzyme in vitro and good interactions with this protein in silico.",

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Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles : a faster access to spirooxindoles of potential pharmacological interest. / Singh, Shambhu Nath; Regati, Sridhar; Paul, Abir Kumar; Layek, Mohosin; Jayaprakash, Sarva; Reddy, K. Venkateshwara; Deora, Girdhar Singh; Mukherjee, Soumita; Pal, Manojit.

In: Tetrahedron Letters, Vol. 54, No. 40, 02.10.2013, p. 5448-5452.

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

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T2 - a faster access to spirooxindoles of potential pharmacological interest

AU - Singh, Shambhu Nath

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AU - Paul, Abir Kumar

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AU - Jayaprakash, Sarva

AU - Reddy, K. Venkateshwara

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AU - Mukherjee, Soumita

AU - Pal, Manojit

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