Journal of the Chemical Society Perkin Transactions 1, issue 24, pages 4265-4278
Synthesis of the farnesyl ether 2,3,5-trifluoro-6-hydroxy-4-[(E,E )-3,7,11-trimethyldodeca-2,6,10-trien-1-yloxy]nitrobenzene, and related compounds containing a substituted hydroxytrifluorophenyl residue: novel inhibitors of protein farnesyltransferase, geranylgeranyltransferase I and squalene synthase
Jonathan H Marriott
1
,
Amelia M Moreno Barber
1
,
Ian R. Hardcastle
1
,
Martin G Rowlands
1
,
RACHEL M. GRIMSHAW
1
,
Stephen Neidle
2
,
MICHAEL JARMAN
1
1
CRC Centre for Cancer Therapeutics, The Institute of Cancer Research, 15 Cotswold Road, Sutton, Surrey, UK
|
2
CRC Biomolecular Structure Unit, Chester Beatty Laboratories, Institute of Cancer Research, Fulham Road, London, UK
|
Publication type: Journal Article
Publication date: 2000-01-01
Quartile SCImago
— Quartile WOS
—
Impact factor: —
ISSN: 0300922X, 13645463, 14727781
DOI:
10.1039/b007101n
General Medicine
Abstract
Pentafluoronitrobenzene was converted via two successive phase-transfer catalysed SNAr reactions with (E,E)-farnesol or geraniol followed by hydroxide ion into the 2,3,6-trifluoro-5-hydroxy-4-nitrophenyl farnesyl ether 3a and the geranyl ether 3b. Analogues containing a cyano (3c) or carbamoyl (3d) group in place of nitro or an epoxygeranyl (3e) group as the prenyl (3-methylbut-2-enyl) containing residue were similarly prepared. Those containing a sulfonic acid (35a, 35b) or a methyl sulfone (41) group were made by modifications of this approach involving the use of protecting groups. The synthesis of carboxy analogues (27a, 27b) involved the alkylation of a protected fluorinated ortho-hydroxybenzoic acid derivative (25) with (E,E)-farnesyl or geranyl bromide. The non-fluorinated compound 18 was analogously prepared via compound 17a. Mitsunobu reactions were used in the synthesis of 15, a dihydroxylated analogue of 3b, and of 8, the non-fluorinated analogue of 3a. The nitro compounds 3a and 3b were moderate inhibitors of both farnesyl transferase and geranylgeranyl transferase I, the geranyl carboxy derivative 27b of the latter enzyme and the farnesyl sulfonic acid derivative 35a of squalene synthase.
Top-30
Citations by journals
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2 publications, 10.53%
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1 publication, 5.26%
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1 publication, 5.26%
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1 publication, 5.26%
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1 publication, 5.26%
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1 publication, 5.26%
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1 publication, 5.26%
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1 publication, 5.26%
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1 publication, 5.26%
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Journal of Medicinal Chemistry
1 publication, 5.26%
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1 publication, 5.26%
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1 publication, 5.26%
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1
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3
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Citations by publishers
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1
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3
4
5
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8
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Elsevier
8 publications, 42.11%
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Wiley
4 publications, 21.05%
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Springer Nature
2 publications, 10.53%
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World Scientific
1 publication, 5.26%
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American Chemical Society (ACS)
1 publication, 5.26%
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Thieme
1 publication, 5.26%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 5.26%
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8
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Marriott J. H. et al. Synthesis of the farnesyl ether 2,3,5-trifluoro-6-hydroxy-4-[(E,E )-3,7,11-trimethyldodeca-2,6,10-trien-1-yloxy]nitrobenzene, and related compounds containing a substituted hydroxytrifluorophenyl residue: novel inhibitors of protein farnesyltransferase, geranylgeranyltransferase I and squalene synthase // Journal of the Chemical Society Perkin Transactions 1. 2000. Vol. 24. pp. 4265-4278.
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Marriott J. H., Barber A. M. M., Hardcastle I. R., Rowlands M. G., GRIMSHAW R. M., Neidle S., JARMAN M. Synthesis of the farnesyl ether 2,3,5-trifluoro-6-hydroxy-4-[(E,E )-3,7,11-trimethyldodeca-2,6,10-trien-1-yloxy]nitrobenzene, and related compounds containing a substituted hydroxytrifluorophenyl residue: novel inhibitors of protein farnesyltransferase, geranylgeranyltransferase I and squalene synthase // Journal of the Chemical Society Perkin Transactions 1. 2000. Vol. 24. pp. 4265-4278.
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TY - JOUR
DO - 10.1039/b007101n
UR - https://doi.org/10.1039/b007101n
TI - Synthesis of the farnesyl ether 2,3,5-trifluoro-6-hydroxy-4-[(E,E )-3,7,11-trimethyldodeca-2,6,10-trien-1-yloxy]nitrobenzene, and related compounds containing a substituted hydroxytrifluorophenyl residue: novel inhibitors of protein farnesyltransferase, geranylgeranyltransferase I and squalene synthase
T2 - Journal of the Chemical Society Perkin Transactions 1
AU - Marriott, Jonathan H
AU - Barber, Amelia M Moreno
AU - Rowlands, Martin G
AU - GRIMSHAW, RACHEL M.
AU - Neidle, Stephen
AU - JARMAN, MICHAEL
AU - Hardcastle, Ian R.
PY - 2000
DA - 2000/01/01 00:00:00
PB - Royal Society of Chemistry (RSC)
SP - 4265-4278
IS - 24
SN - 0300-922X
SN - 1364-5463
SN - 1472-7781
ER -
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@article{2000_Marriott,
author = {Jonathan H Marriott and Amelia M Moreno Barber and Martin G Rowlands and RACHEL M. GRIMSHAW and Stephen Neidle and MICHAEL JARMAN and Ian R. Hardcastle},
title = {Synthesis of the farnesyl ether 2,3,5-trifluoro-6-hydroxy-4-[(E,E )-3,7,11-trimethyldodeca-2,6,10-trien-1-yloxy]nitrobenzene, and related compounds containing a substituted hydroxytrifluorophenyl residue: novel inhibitors of protein farnesyltransferase, geranylgeranyltransferase I and squalene synthase},
journal = {Journal of the Chemical Society Perkin Transactions 1},
year = {2000},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://doi.org/10.1039/b007101n},
number = {24},
pages = {4265--4278},
doi = {10.1039/b007101n}
}