Synthesis and Biological Activities of Conformationally Restricted Cyclopentenyl-Glutamate Analogues

A.T. Ung; K. Schafer; K.B. Lindsay; S.G. Pyne; K. Amornraksa; R. Wouters; I. Van Der Linden; I. Biesmans; A.S.J. Lesage; Brian Skelton; Allan White

doi:10.1021/jo010864i

Synthesis and Biological Activities of Conformationally Restricted Cyclopentenyl-Glutamate Analogues

A.T. Ung, K. Schafer, K.B. Lindsay, S.G. Pyne, K. Amornraksa, R. Wouters, I. Van Der Linden, I. Biesmans, A.S.J. Lesage, Brian Skelton, Allan White

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Abstract

An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds have also been devised. Of these compounds, (S)-2 is an agonist at the mGlu5 (EC50 18 muM) and mGlu2 (EC50 45 muM) receptors.

Original language	English
Pages (from-to)	227-233
Journal	Journal of Organic Chemistry
Volume	67
Issue number	n/a
DOIs	https://doi.org/10.1021/jo010864i
Publication status	Published - 2002

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title = "Synthesis and Biological Activities of Conformationally Restricted Cyclopentenyl-Glutamate Analogues",

abstract = "An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds have also been devised. Of these compounds, (S)-2 is an agonist at the mGlu5 (EC50 18 muM) and mGlu2 (EC50 45 muM) receptors.",

author = "A.T. Ung and K. Schafer and K.B. Lindsay and S.G. Pyne and K. Amornraksa and R. Wouters and {Van Der Linden}, I. and I. Biesmans and A.S.J. Lesage and Brian Skelton and Allan White",

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doi = "10.1021/jo010864i",

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T1 - Synthesis and Biological Activities of Conformationally Restricted Cyclopentenyl-Glutamate Analogues

AU - Ung, A.T.

AU - Schafer, K.

AU - Lindsay, K.B.

AU - Pyne, S.G.

AU - Amornraksa, K.

AU - Wouters, R.

AU - Van Der Linden, I.

AU - Biesmans, I.

AU - Lesage, A.S.J.

AU - Skelton, Brian

AU - White, Allan

PY - 2002

Y1 - 2002

N2 - An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds have also been devised. Of these compounds, (S)-2 is an agonist at the mGlu5 (EC50 18 muM) and mGlu2 (EC50 45 muM) receptors.

AB - An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds have also been devised. Of these compounds, (S)-2 is an agonist at the mGlu5 (EC50 18 muM) and mGlu2 (EC50 45 muM) receptors.

U2 - 10.1021/jo010864i

DO - 10.1021/jo010864i

M3 - Article

SN - 0022-3263

VL - 67

SP - 227

EP - 233

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - n/a

ER -

Synthesis and Biological Activities of Conformationally Restricted Cyclopentenyl-Glutamate Analogues

Abstract

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