Microwave-Enhanced α-Arylation of a Protected Glycine in Water:Evaluation of 3-Phenylglycine Derivatives as Inhibitors of the Tuberculosis Enzyme, Glutamine Synthetase

Olof Lagerlund; Luke R. Odell; Sherry L. Mowbray; Mikael T. Nilsson; Wojciech W. Krajewski; Anneli Nordqvist; Anders Karlen; Mats Larhed

doi:10.2174/138620707783018478

ISSN: 1386-2073
E-ISSN: 1875-5402

Microwave-Enhanced α-Arylation of a Protected Glycine in Water:Evaluation of 3-Phenylglycine Derivatives as Inhibitors of the Tuberculosis Enzyme, Glutamine Synthetase
Authors: Olof Lagerlund¹, Luke R. Odell², Sherry L. Mowbray³, Mikael T. Nilsson⁴, Wojciech W. Krajewski⁵, Anneli Nordqvist⁶, Anders Karlen⁷ and Mats Larhed⁸
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¹ Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, Biomedical Center, Box 574, SE- 751 23 Uppsala, Sweden. ² Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, Biomedical Center, Box 574, SE- 751 23 Uppsala, Sweden. ³ Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, Biomedical Center, Box 574, SE- 751 23 Uppsala, Sweden. ⁴ Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, Biomedical Center, Box 574, SE- 751 23 Uppsala, Sweden. ⁵ Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, Biomedical Center, Box 574, SE- 751 23 Uppsala, Sweden. ⁶ Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, Biomedical Center, Box 574, SE- 751 23 Uppsala, Sweden. ⁷ Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, Biomedical Center, Box 574, SE- 751 23 Uppsala, Sweden. ⁸ Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, Biomedical Center, Box 574, SE- 751 23 Uppsala, Sweden.
Source: Combinatorial Chemistry & High Throughput Screening, Volume 10, Issue 9, Nov 2007, p. 783 - 789
DOI: https://doi.org/10.2174/138620707783018478
- Available online: 01 Nov 2007

Abstract

A microwave-enhanced, palladium-catalyzed protocol for the α-arylation of a protected glycine in neat water is described. This reaction proceeds rapidly, under non-inert conditions, to afford a range of phenylglycine derivatives in moderate to good yields. Based on this α-arylation, a number of aryl L-methionine-SR-sulfoximine (MSO) analogues were prepared and evaluated for their Mycobacterium tuberculosis glutamine synthetase (TB-GS) inhibitory activity.

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2007-11-01

2025-04-23

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Article Type: Research Article

Keyword(s): Arylation; glutamine synthetase; microwave; palladium; tuberculosis; water

Microwave-Enhanced α-Arylation of a Protected Glycine in Water:Evaluation of 3-Phenylglycine Derivatives as Inhibitors of the Tuberculosis Enzyme, Glutamine Synthetase

Abstract

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