New salicylamide and sulfonamide derivatives of quinoxaline 1,4-di-N-oxide with antileishmanial and antimalarial activities

Carlos Barea; Adriana Pabón; Denis Castillo; Mirko Zimic; Miguel Quiliano; Silvia Galiano; Silvia Pérez-Silanes; Antonio Monge; Eric Deharo; Ignacio Aldana

doi:10.1016/j.bmcl.2011.05.125

New salicylamide and sulfonamide derivatives of quinoxaline 1,4-di-N-oxide with antileishmanial and antimalarial activities

Carlos Barea, Adriana Pabón, Denis Castillo, Mirko Zimic, Miguel Quiliano, Silvia Galiano, Silvia Pérez-Silanes, Antonio Monge, Eric Deharo, Ignacio Aldana

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

49 Scopus citations

Abstract

Continuing with our efforts to identify new active compounds against malaria and leishmaniasis, 14 new 3-amino-1,4-di-N-oxide quinoxaline-2- carbonitrile derivatives were synthesized and evaluated for their in vitro antimalarial and antileishmanial activity against Plasmodium falciparum Colombian FCR-3 strain and Leishmania amazonensis strain MHOM/BR/76/LTB-012A. Further computational studies were carried out in order to analyze graphic SAR and ADME properties. The results obtained indicate that compounds with one halogenous group substituted in position 6 and 7 provide an efficient approach for further development of antimalarial and antileishmanial agents. In addition, interesting ADME properties were found.

Original language	English (US)
Pages (from-to)	4498-4502
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	15
DOIs	https://doi.org/10.1016/j.bmcl.2011.05.125
State	Published - Aug 1 2011
Externally published	Yes

Keywords

Leishmaniasis
Malaria
N-Oxides
Quinoxaline

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2011.05.125

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Barea, C, Pabón, A, Castillo, D, Zimic, M, Quiliano, M, Galiano, S, Pérez-Silanes, S, Monge, A, Deharo, E & Aldana, I 2011, 'New salicylamide and sulfonamide derivatives of quinoxaline 1,4-di-N-oxide with antileishmanial and antimalarial activities', Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 15, pp. 4498-4502. https://doi.org/10.1016/j.bmcl.2011.05.125

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title = "New salicylamide and sulfonamide derivatives of quinoxaline 1,4-di-N-oxide with antileishmanial and antimalarial activities",

abstract = "Continuing with our efforts to identify new active compounds against malaria and leishmaniasis, 14 new 3-amino-1,4-di-N-oxide quinoxaline-2- carbonitrile derivatives were synthesized and evaluated for their in vitro antimalarial and antileishmanial activity against Plasmodium falciparum Colombian FCR-3 strain and Leishmania amazonensis strain MHOM/BR/76/LTB-012A. Further computational studies were carried out in order to analyze graphic SAR and ADME properties. The results obtained indicate that compounds with one halogenous group substituted in position 6 and 7 provide an efficient approach for further development of antimalarial and antileishmanial agents. In addition, interesting ADME properties were found.",

keywords = "Leishmaniasis, Malaria, N-Oxides, Quinoxaline",

author = "Carlos Barea and Adriana Pab{\'o}n and Denis Castillo and Mirko Zimic and Miguel Quiliano and Silvia Galiano and Silvia P{\'e}rez-Silanes and Antonio Monge and Eric Deharo and Ignacio Aldana",

note = "Funding Information: The authors gratefully acknowledge the {\textquoteleft}Oficina de Cooperaci{\'o}n de la Embajada de B{\'e}lgica{\textquoteright} for funding a Master Scholarship to Denis Castillo. Carlos Barea is indebted to the University of Navarra (Spain) for PhD scholarship. ",

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doi = "10.1016/j.bmcl.2011.05.125",

language = "English (US)",

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T1 - New salicylamide and sulfonamide derivatives of quinoxaline 1,4-di-N-oxide with antileishmanial and antimalarial activities

AU - Barea, Carlos

AU - Pabón, Adriana

AU - Castillo, Denis

AU - Zimic, Mirko

AU - Quiliano, Miguel

AU - Galiano, Silvia

AU - Pérez-Silanes, Silvia

AU - Monge, Antonio

AU - Deharo, Eric

AU - Aldana, Ignacio

N1 - Funding Information: The authors gratefully acknowledge the ‘Oficina de Cooperación de la Embajada de Bélgica’ for funding a Master Scholarship to Denis Castillo. Carlos Barea is indebted to the University of Navarra (Spain) for PhD scholarship.

PY - 2011/8/1

Y1 - 2011/8/1

N2 - Continuing with our efforts to identify new active compounds against malaria and leishmaniasis, 14 new 3-amino-1,4-di-N-oxide quinoxaline-2- carbonitrile derivatives were synthesized and evaluated for their in vitro antimalarial and antileishmanial activity against Plasmodium falciparum Colombian FCR-3 strain and Leishmania amazonensis strain MHOM/BR/76/LTB-012A. Further computational studies were carried out in order to analyze graphic SAR and ADME properties. The results obtained indicate that compounds with one halogenous group substituted in position 6 and 7 provide an efficient approach for further development of antimalarial and antileishmanial agents. In addition, interesting ADME properties were found.

AB - Continuing with our efforts to identify new active compounds against malaria and leishmaniasis, 14 new 3-amino-1,4-di-N-oxide quinoxaline-2- carbonitrile derivatives were synthesized and evaluated for their in vitro antimalarial and antileishmanial activity against Plasmodium falciparum Colombian FCR-3 strain and Leishmania amazonensis strain MHOM/BR/76/LTB-012A. Further computational studies were carried out in order to analyze graphic SAR and ADME properties. The results obtained indicate that compounds with one halogenous group substituted in position 6 and 7 provide an efficient approach for further development of antimalarial and antileishmanial agents. In addition, interesting ADME properties were found.

KW - Leishmaniasis

KW - Malaria

KW - N-Oxides

KW - Quinoxaline

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New salicylamide and sulfonamide derivatives of quinoxaline 1,4-di-N-oxide with antileishmanial and antimalarial activities

Abstract

Keywords

ASJC Scopus subject areas

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