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

46 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

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10.1016/j.tetlet.2013.07.126

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

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.",

keywords = "CuI, MCR, PDE4B, Spirooxindole",

author = "Singh, {Shambhu Nath} and Sridhar Regati and Paul, {Abir Kumar} and Mohosin Layek and Sarva Jayaprakash and Reddy, {K. Venkateshwara} and Deora, {Girdhar Singh} and Soumita Mukherjee and Manojit Pal",

year = "2013",

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doi = "10.1016/j.tetlet.2013.07.126",

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journal = "Tetrahedron Letters",

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T1 - Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles

T2 - a faster access to spirooxindoles of potential pharmacological interest

AU - Singh, Shambhu Nath

AU - Regati, Sridhar

AU - Paul, Abir Kumar

AU - Layek, Mohosin

AU - Jayaprakash, Sarva

AU - Reddy, K. Venkateshwara

AU - Deora, Girdhar Singh

AU - Mukherjee, Soumita

AU - Pal, Manojit

PY - 2013/10/2

Y1 - 2013/10/2

N2 - 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.

AB - 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.

KW - CuI

KW - MCR

KW - PDE4B

KW - Spirooxindole

UR - http://www.scopus.com/inward/record.url?scp=84883452412&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.07.126

DO - 10.1016/j.tetlet.2013.07.126

M3 - Article

AN - SCOPUS:84883452412

SN - 0040-4039

VL - 54

SP - 5448

EP - 5452

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

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

Abstract

Keywords

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