A new Heck reaction modification using ketone Mannich bases as enone precursors: parallel synthesis of anti-leishmanial chalcones.
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.
Reichwald
Christina
C
Technische Universität Braunschweig, Institut für Pharmazeutische Chemie, 38106 Braunschweig, Germany.
Shimony
Orly
O
Sacerdoti-Sierra
Nina
N
Jaffe
Charles L
CL
Kunick
Conrad
C
D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001549:Benzamides / Q000138:chemical synthesis* / Q000494:pharmacology*; D002478:Cells, Cultured; D002851:Chromatography, High Pressure Liquid; D003460:Crystallization; D007659:Ketones / Q000737:chemistry*; D007893:Leishmania donovani / Q000187:drug effects*; D007896:Leishmaniasis / Q000188:drug therapy* / Q000469:parasitology; D008264:Macrophages / Q000166:cytology / Q000187:drug effects; D008352:Mannich Bases / Q000737:chemistry*; D015394:Molecular Structure
D000981:Antiprotozoal Agents; D001549:Benzamides; D007659:Ketones; D008352:Mannich Bases; C529331:N-(4-((1E)-3-oxo-3-(3-pyridinyl)-1-propenyl)phenyl)benzamide