Synthesis and antimalarial activity of new haemanthamine-type derivatives

Juan C. Cedrón; David Gutiérrez; Esther Ninoska Flores Quisbert Flores Quisbert; Ángel G. Ravelo; Ana Estévez-Braun

doi:10.1016/j.bmc.2012.07.036

Synthesis and antimalarial activity of new haemanthamine-type derivatives

Juan C. Cedrón, David Gutiérrez, Esther Ninoska Flores Quisbert Flores Quisbert, Ángel G. Ravelo, Ana Estévez-Braun

Resultado de la investigación: Contribución a una revista › Artículo › revisión exhaustiva

28 Citas (Scopus)

Resumen

Thirty one derivatives were prepared from the natural alkaloids haemanthamine (1), haemanthidine (2) and 11-hydroxyvittatine (3). They were evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum and some structure-activity relationships were outlined. For haemanthamine derivatives having a methoxy group at C-3, the presence of a free hydroxyl group at C-11 is important for the activity. The double bond at C-1-C-2 plays also an important role to achieve good inhibitory activity. Compound 35 with two nicotinate groups at C-3 and at C-11 was the most active compound with a IC₅₀ = 0.8 ± 0.06 μM.

Idioma original	Inglés
Páginas (desde-hasta)	5464-5472
Número de páginas	9
Publicación	Bioorganic and Medicinal Chemistry
Volumen	20
N.º	18
DOI	https://doi.org/10.1016/j.bmc.2012.07.036
Estado	Publicada - 15 sep. 2012

Nota bibliográfica

Funding Information:
This work has been partly funded by the Spanish MICINN (SAF 2009-13296-C02-01) and ICIC (Instituto Canario de Investigación del Cáncer). J.C.C. thanks Gobierno Autónomo de Canarias for a predoctoral fellowship.

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10.1016/j.bmc.2012.07.036

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title = "Synthesis and antimalarial activity of new haemanthamine-type derivatives",

abstract = "Thirty one derivatives were prepared from the natural alkaloids haemanthamine (1), haemanthidine (2) and 11-hydroxyvittatine (3). They were evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum and some structure-activity relationships were outlined. For haemanthamine derivatives having a methoxy group at C-3, the presence of a free hydroxyl group at C-11 is important for the activity. The double bond at C-1-C-2 plays also an important role to achieve good inhibitory activity. Compound 35 with two nicotinate groups at C-3 and at C-11 was the most active compound with a IC50 = 0.8 ± 0.06 μM.",

keywords = "Amaryllidaceae alkaloids, Antiplasmodial activity, Haemanthamine",

author = "Cedr{\'o}n, {Juan C.} and David Guti{\'e}rrez and {Flores Quisbert}, {Esther Ninoska Flores Quisbert} and Ravelo, {{\'A}ngel G.} and Ana Est{\'e}vez-Braun",

note = "Funding Information: This work has been partly funded by the Spanish MICINN (SAF 2009-13296-C02-01) and ICIC (Instituto Canario de Investigaci{\'o}n del C{\'a}ncer). J.C.C. thanks Gobierno Aut{\'o}nomo de Canarias for a predoctoral fellowship. ",

year = "2012",

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day = "15",

doi = "10.1016/j.bmc.2012.07.036",

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AU - Cedrón, Juan C.

AU - Gutiérrez, David

AU - Flores Quisbert, Esther Ninoska Flores Quisbert

AU - Ravelo, Ángel G.

AU - Estévez-Braun, Ana

N1 - Funding Information: This work has been partly funded by the Spanish MICINN (SAF 2009-13296-C02-01) and ICIC (Instituto Canario de Investigación del Cáncer). J.C.C. thanks Gobierno Autónomo de Canarias for a predoctoral fellowship.

PY - 2012/9/15

Y1 - 2012/9/15

N2 - Thirty one derivatives were prepared from the natural alkaloids haemanthamine (1), haemanthidine (2) and 11-hydroxyvittatine (3). They were evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum and some structure-activity relationships were outlined. For haemanthamine derivatives having a methoxy group at C-3, the presence of a free hydroxyl group at C-11 is important for the activity. The double bond at C-1-C-2 plays also an important role to achieve good inhibitory activity. Compound 35 with two nicotinate groups at C-3 and at C-11 was the most active compound with a IC50 = 0.8 ± 0.06 μM.

AB - Thirty one derivatives were prepared from the natural alkaloids haemanthamine (1), haemanthidine (2) and 11-hydroxyvittatine (3). They were evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum and some structure-activity relationships were outlined. For haemanthamine derivatives having a methoxy group at C-3, the presence of a free hydroxyl group at C-11 is important for the activity. The double bond at C-1-C-2 plays also an important role to achieve good inhibitory activity. Compound 35 with two nicotinate groups at C-3 and at C-11 was the most active compound with a IC50 = 0.8 ± 0.06 μM.

KW - Amaryllidaceae alkaloids

KW - Antiplasmodial activity

KW - Haemanthamine

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M3 - Artículo

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AN - SCOPUS:84866256473

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EP - 5472

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

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ER -

Synthesis and antimalarial activity of new haemanthamine-type derivatives

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