Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles and their analogs, and evaluation of biological activity against Leishmania donovani

Leena Keurulainen; Mikko Heiskari; Satu Nenonen; Abedelmajeed Nasereddin; Dmitry Kopelyanskiy; Teppo O. Leino; Jari Yli-Kauhaluoma; Charles L. Jaffe; Paula Kiuru

doi:10.1039/c5md00119f

Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles and their analogs, and evaluation of biological activity against Leishmania donovani

Leena Keurulainen, Mikko Heiskari, Satu Nenonen, Abedelmajeed Nasereddin, Dmitry Kopelyanskiy, Teppo O. Leino, Jari Yli-Kauhaluoma, Charles L. Jaffe, Paula Kiuru^*

^*Corresponding author for this work

Institute for Medical Research Israel-Canada (IMRIC)

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

7 Scopus citations

Abstract

A facile synthesis route to carboxyimidamide-substituted benzoxadiazoles and related derivatives was developed. A total of 25 derivatives were synthesized. They were evaluated for antileishmanial activity by inhibition of Leishmania donovani axenic amastigote growth using a fluorescent viability microplate assay. The most promising derivative (14) demonstrated an antileishmanial EC₅₀ of 4.0 μM, and it also showed activity in infected macrophages (EC₅₀ 5.92 μM) without signs of cytotoxicity.

Original language	English
Pages (from-to)	1673-1678
Number of pages	6
Journal	MedChemComm
Volume	6
Issue number	9
DOIs	https://doi.org/10.1039/c5md00119f
State	Published - 29 Jul 2015

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© The Royal Society of Chemistry.

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title = "Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles and their analogs, and evaluation of biological activity against Leishmania donovani",

abstract = "A facile synthesis route to carboxyimidamide-substituted benzoxadiazoles and related derivatives was developed. A total of 25 derivatives were synthesized. They were evaluated for antileishmanial activity by inhibition of Leishmania donovani axenic amastigote growth using a fluorescent viability microplate assay. The most promising derivative (14) demonstrated an antileishmanial EC50 of 4.0 μM, and it also showed activity in infected macrophages (EC50 5.92 μM) without signs of cytotoxicity.",

author = "Leena Keurulainen and Mikko Heiskari and Satu Nenonen and Abedelmajeed Nasereddin and Dmitry Kopelyanskiy and Leino, {Teppo O.} and Jari Yli-Kauhaluoma and Jaffe, {Charles L.} and Paula Kiuru",

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year = "2015",

month = jul,

day = "29",

doi = "10.1039/c5md00119f",

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AU - Keurulainen, Leena

AU - Heiskari, Mikko

AU - Nenonen, Satu

AU - Nasereddin, Abedelmajeed

AU - Kopelyanskiy, Dmitry

AU - Leino, Teppo O.

AU - Yli-Kauhaluoma, Jari

AU - Jaffe, Charles L.

AU - Kiuru, Paula

PY - 2015/7/29

Y1 - 2015/7/29

N2 - A facile synthesis route to carboxyimidamide-substituted benzoxadiazoles and related derivatives was developed. A total of 25 derivatives were synthesized. They were evaluated for antileishmanial activity by inhibition of Leishmania donovani axenic amastigote growth using a fluorescent viability microplate assay. The most promising derivative (14) demonstrated an antileishmanial EC50 of 4.0 μM, and it also showed activity in infected macrophages (EC50 5.92 μM) without signs of cytotoxicity.

AB - A facile synthesis route to carboxyimidamide-substituted benzoxadiazoles and related derivatives was developed. A total of 25 derivatives were synthesized. They were evaluated for antileishmanial activity by inhibition of Leishmania donovani axenic amastigote growth using a fluorescent viability microplate assay. The most promising derivative (14) demonstrated an antileishmanial EC50 of 4.0 μM, and it also showed activity in infected macrophages (EC50 5.92 μM) without signs of cytotoxicity.

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Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles and their analogs, and evaluation of biological activity against Leishmania donovani

Abstract

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