Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates

Nuna C.P. Araújo; Victoria Barton; Michael Jones; Paul A. Stocks; Steve Ward; Jill Davies; Patrick G. Bray; Alison E. Shone; Maria L.S. Cristiano; Paul M. O'Neill

doi:10.1016/j.bmcl.2009.02.013

Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates

Nuna C.P. Araújo, Victoria Barton, Michael Jones, Paul A. Stocks, Steve Ward, Jill Davies, Patrick G. Bray, Alison E. Shone, Maria L.S. Cristiano, Paul M. O'Neill

Tropical Disease Biology

Research output: Contribution to journal › Article › peer-review

69 Citations (Scopus)

Abstract

A novel series of semi-synthetic trioxaquines and synthetic trioxolaquines were prepared, in moderate to good yields. Antimalarial activity was evaluated against both the chloroquine-sensitive 3D7 and resistant K1 strain of Plasmodium falciparum and both series of compounds were shown to be active in the low nanomolar range. For comparison the corresponding 9-amino acridine analogues were also prepared and shown to have low nanomolar activity like their quinoline counterparts. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2038-2043
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	7
DOIs	https://doi.org/10.1016/j.bmcl.2009.02.013
Publication status	Published - 1 Apr 2009

Keywords

Antimalarial
Drug-hybrid
Plasmodium falciparum
Resistance

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10.1016/j.bmcl.2009.02.013

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Araújo, N. C. P., Barton, V., Jones, M., Stocks, P. A., Ward, S., Davies, J., Bray, P. G., Shone, A. E., Cristiano, M. L. S., & O'Neill, P. M. (2009). Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates. Bioorganic and Medicinal Chemistry Letters, 19(7), 2038-2043. https://doi.org/10.1016/j.bmcl.2009.02.013

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title = "Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates",

abstract = "A novel series of semi-synthetic trioxaquines and synthetic trioxolaquines were prepared, in moderate to good yields. Antimalarial activity was evaluated against both the chloroquine-sensitive 3D7 and resistant K1 strain of Plasmodium falciparum and both series of compounds were shown to be active in the low nanomolar range. For comparison the corresponding 9-amino acridine analogues were also prepared and shown to have low nanomolar activity like their quinoline counterparts. (C) 2009 Elsevier Ltd. All rights reserved.",

keywords = "Antimalarial, Drug-hybrid, Plasmodium falciparum, Resistance",

author = "Ara{\'u}jo, \{Nuna C.P.\} and Victoria Barton and Michael Jones and Stocks, \{Paul A.\} and Steve Ward and Jill Davies and Bray, \{Patrick G.\} and Shone, \{Alison E.\} and Cristiano, \{Maria L.S.\} and O'Neill, \{Paul M.\}",

year = "2009",

month = apr,

day = "1",

doi = "10.1016/j.bmcl.2009.02.013",

language = "English",

volume = "19",

pages = "2038--2043",

journal = "Bioorganic and Medicinal Chemistry Letters",

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Araújo, NCP, Barton, V, Jones, M, Stocks, PA, Ward, S , Davies, J, Bray, PG, Shone, AE, Cristiano, MLS & O'Neill, PM 2009, 'Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates', Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 7, pp. 2038-2043. https://doi.org/10.1016/j.bmcl.2009.02.013

Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates. / Araújo, Nuna C.P.; Barton, Victoria; Jones, Michael et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 19, No. 7, 01.04.2009, p. 2038-2043.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates

AU - Araújo, Nuna C.P.

AU - Barton, Victoria

AU - Jones, Michael

AU - Stocks, Paul A.

AU - Ward, Steve

AU - Davies, Jill

AU - Bray, Patrick G.

AU - Shone, Alison E.

AU - Cristiano, Maria L.S.

AU - O'Neill, Paul M.

PY - 2009/4/1

Y1 - 2009/4/1

N2 - A novel series of semi-synthetic trioxaquines and synthetic trioxolaquines were prepared, in moderate to good yields. Antimalarial activity was evaluated against both the chloroquine-sensitive 3D7 and resistant K1 strain of Plasmodium falciparum and both series of compounds were shown to be active in the low nanomolar range. For comparison the corresponding 9-amino acridine analogues were also prepared and shown to have low nanomolar activity like their quinoline counterparts. (C) 2009 Elsevier Ltd. All rights reserved.

AB - A novel series of semi-synthetic trioxaquines and synthetic trioxolaquines were prepared, in moderate to good yields. Antimalarial activity was evaluated against both the chloroquine-sensitive 3D7 and resistant K1 strain of Plasmodium falciparum and both series of compounds were shown to be active in the low nanomolar range. For comparison the corresponding 9-amino acridine analogues were also prepared and shown to have low nanomolar activity like their quinoline counterparts. (C) 2009 Elsevier Ltd. All rights reserved.

KW - Antimalarial

KW - Drug-hybrid

KW - Plasmodium falciparum

KW - Resistance

U2 - 10.1016/j.bmcl.2009.02.013

DO - 10.1016/j.bmcl.2009.02.013

M3 - Article

SN - 0960-894X

VL - 19

SP - 2038

EP - 2043

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 7

ER -

Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates

Abstract

Keywords

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