Microwave-enhanced alpha-arylation of a protected glycine in water: Evaluation of 3-phenylglycine derivatives as inhibitors of the tuberculosis enzyme, glutamine synthetase

Sherry Mowbray; Olof Lagerlund; Mats Larhed; Mikael Nilsson; Luke R Odell; Anders Karlén; Anneli Nordqvist; W W Krajewski

doi:10.2174/138620707783018478

Microwave-enhanced alpha-arylation of a protected glycine in water: Evaluation of 3-phenylglycine derivatives as inhibitors of the tuberculosis enzyme, glutamine synthetase

Sherry Mowbray
, Olof Lagerlund
, Mats Larhed
, Mikael Nilsson
, Luke R Odell
, Anders Karlén
, Anneli Nordqvist
, W W Krajewski

Publication: Contribution to journal › Journal article › peer-review

Abstract

A microwave-enhanced, palladium-catalyzed protocol for the alpha-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 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.

Original language	English
Pages (from-to)	783-789
Number of pages	7
Journal	Combinatorial Chemistry and High Throughput Screening
Volume	10
Issue number	9
DOIs	https://doi.org/10.2174/138620707783018478
Publication status	Published - 2007

Keywords

arylation
glutamine synthetase
microwave
palladium
tuberculosis
water

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10.2174/138620707783018478

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Mowbray, S., Lagerlund, O., Larhed, M., Nilsson, M., Odell, L. R., Karlén, A., Nordqvist, A., & Krajewski, W. W. (2007). Microwave-enhanced alpha-arylation of a protected glycine in water: Evaluation of 3-phenylglycine derivatives as inhibitors of the tuberculosis enzyme, glutamine synthetase. Combinatorial Chemistry and High Throughput Screening, 10(9), 783-789. https://doi.org/10.2174/138620707783018478

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title = "Microwave-enhanced alpha-arylation of a protected glycine in water: Evaluation of 3-phenylglycine derivatives as inhibitors of the tuberculosis enzyme, glutamine synthetase",

abstract = "A microwave-enhanced, palladium-catalyzed protocol for the alpha-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 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.",

keywords = "arylation, glutamine synthetase, microwave, palladium, tuberculosis, water, arylation, glutamine synthetase, microwave, palladium, tuberculosis, water",

author = "Sherry Mowbray and Olof Lagerlund and Mats Larhed and Mikael Nilsson and Odell, \{Luke R\} and Anders Karl{\'e}n and Anneli Nordqvist and Krajewski, \{W W\}",

year = "2007",

doi = "10.2174/138620707783018478",

language = "English",

volume = "10",

pages = "783--789",

journal = "Combinatorial Chemistry and High Throughput Screening",

issn = "1386-2073",

publisher = "Bentham Science Publishers",

number = "9",

}

Mowbray, S, Lagerlund, O, Larhed, M, Nilsson, M, Odell, LR, Karlén, A, Nordqvist, A & Krajewski, WW 2007, 'Microwave-enhanced alpha-arylation of a protected glycine in water: Evaluation of 3-phenylglycine derivatives as inhibitors of the tuberculosis enzyme, glutamine synthetase', Combinatorial Chemistry and High Throughput Screening, vol. 10, no. 9, pp. 783-789. https://doi.org/10.2174/138620707783018478

Microwave-enhanced alpha-arylation of a protected glycine in water: Evaluation of 3-phenylglycine derivatives as inhibitors of the tuberculosis enzyme, glutamine synthetase. / Mowbray, Sherry; Lagerlund, Olof; Larhed, Mats et al.
In: Combinatorial Chemistry and High Throughput Screening, Vol. 10, No. 9, 2007, p. 783-789.

Publication: Contribution to journal › Journal article › peer-review

TY - JOUR

T1 - Microwave-enhanced alpha-arylation of a protected glycine in water: Evaluation of 3-phenylglycine derivatives as inhibitors of the tuberculosis enzyme, glutamine synthetase

AU - Mowbray, Sherry

AU - Lagerlund, Olof

AU - Larhed, Mats

AU - Nilsson, Mikael

AU - Odell, Luke R

AU - Karlén, Anders

AU - Nordqvist, Anneli

AU - Krajewski, W W

PY - 2007

Y1 - 2007

N2 - A microwave-enhanced, palladium-catalyzed protocol for the alpha-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 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.

AB - A microwave-enhanced, palladium-catalyzed protocol for the alpha-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 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.

KW - arylation

KW - glutamine synthetase

KW - microwave

KW - palladium

KW - tuberculosis

KW - water

KW - arylation

KW - glutamine synthetase

KW - microwave

KW - palladium

KW - tuberculosis

KW - water

UR - https://res.slu.se/id/publ/16957

U2 - 10.2174/138620707783018478

DO - 10.2174/138620707783018478

M3 - Journal article

C2 - 18478959

SN - 1386-2073

VL - 10

SP - 783

EP - 789

JO - Combinatorial Chemistry and High Throughput Screening

JF - Combinatorial Chemistry and High Throughput Screening

IS - 9

ER -

Microwave-enhanced alpha-arylation of a protected glycine in water: Evaluation of 3-phenylglycine derivatives as inhibitors of the tuberculosis enzyme, glutamine synthetase

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