A new Heck reaction modification using ketone Mannich bases as enone precursors: Parallel synthesis of anti-leishmanial chalcones

Christina Reichwald; Orly Shimony; Nina Sacerdoti-Sierra; Charles L. Jaffe; Conrad Kunick

doi:10.1016/j.bmcl.2008.01.112

A new Heck reaction modification using ketone Mannich bases as enone precursors: Parallel synthesis of anti-leishmanial chalcones

Christina Reichwald
, Orly Shimony
, Nina Sacerdoti-Sierra
, Charles L. Jaffe
, Conrad Kunick^*

^*Corresponding author for this work

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

23 Scopus citations

Abstract

A new Heck-type reaction for the synthesis of chalcones has been established using Mannich bases as enone precursors. The novel reaction proceeds rapidly in air atmosphere under ligandless conditions and can be adapted for library synthesis in a parallel reactor station. Screening of the synthesized chalcones revealed N-{4-[(1E)-3-oxo-3-(3-pyridinyl)-1-propenyl]phenyl}benzamide (3f) to be a potent anti-leishmanial agent.

Original language	English
Pages (from-to)	1985-1989
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2008.01.112
State	Published - 15 Mar 2008

Bibliographical note

Funding Information:
Funding by a grant of the European Commission (Contract No. LSHB-CT-2004-503467; to C.R., C.L.J., and C.K.) is gratefully acknowledged.

Keywords

Chalcones
Heck reaction
Leishmania

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10.1016/j.bmcl.2008.01.112

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title = "A new Heck reaction modification using ketone Mannich bases as enone precursors: Parallel synthesis of anti-leishmanial chalcones",

abstract = "A new Heck-type reaction for the synthesis of chalcones has been established using Mannich bases as enone precursors. The novel reaction proceeds rapidly in air atmosphere under ligandless conditions and can be adapted for library synthesis in a parallel reactor station. Screening of the synthesized chalcones revealed N-\{4-[(1E)-3-oxo-3-(3-pyridinyl)-1-propenyl]phenyl\}benzamide (3f) to be a potent anti-leishmanial agent.",

keywords = "Chalcones, Heck reaction, Leishmania",

author = "Christina Reichwald and Orly Shimony and Nina Sacerdoti-Sierra and Jaffe, \{Charles L.\} and Conrad Kunick",

note = "Funding Information: Funding by a grant of the European Commission (Contract No. LSHB-CT-2004-503467; to C.R., C.L.J., and C.K.) is gratefully acknowledged.",

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doi = "10.1016/j.bmcl.2008.01.112",

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AU - Shimony, Orly

AU - Sacerdoti-Sierra, Nina

AU - Jaffe, Charles L.

AU - Kunick, Conrad

N1 - Funding Information: Funding by a grant of the European Commission (Contract No. LSHB-CT-2004-503467; to C.R., C.L.J., and C.K.) is gratefully acknowledged.

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N2 - A new Heck-type reaction for the synthesis of chalcones has been established using Mannich bases as enone precursors. The novel reaction proceeds rapidly in air atmosphere under ligandless conditions and can be adapted for library synthesis in a parallel reactor station. Screening of the synthesized chalcones revealed N-{4-[(1E)-3-oxo-3-(3-pyridinyl)-1-propenyl]phenyl}benzamide (3f) to be a potent anti-leishmanial agent.

AB - A new Heck-type reaction for the synthesis of chalcones has been established using Mannich bases as enone precursors. The novel reaction proceeds rapidly in air atmosphere under ligandless conditions and can be adapted for library synthesis in a parallel reactor station. Screening of the synthesized chalcones revealed N-{4-[(1E)-3-oxo-3-(3-pyridinyl)-1-propenyl]phenyl}benzamide (3f) to be a potent anti-leishmanial agent.

KW - Chalcones

KW - Heck reaction

KW - Leishmania

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AN - SCOPUS:40749144801

SN - 0960-894X

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EP - 1989

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 6

ER -

A new Heck reaction modification using ketone Mannich bases as enone precursors: Parallel synthesis of anti-leishmanial chalcones

Abstract

Bibliographical note

Keywords

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