Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective saucy-marbet claisen rearrangement
Saucy selection: The first catalytic, enantioselective Saucy-Marbet Claisen rearrangement has been achieved. Palladium(II) (R)-binap or tBuphox catalysts L*Pd(SbF6)2 were employed to generate allenyl oxindoles or spirolactones bearin
Cao, Trung,Deitch, Joshua,Linton, Elizabeth C.,Kozlowski, Marisa C.
supporting information; experimental part
p. 2448 - 2451
(2012/04/23)
Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents
A series of bis(indolyl) hydrazide-hydrazones 5a-n were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-carboxaldehyde 2 with indole-3-carbohydrazide 4 in presence of catalytic amount of acetic acid afforded 5a-n in good yields. Among the synthesized bis(indolyl)hydrazide-hydrazones, the compound 5b with N-(p-chlorobenzyl) and bromo substituents was found to be the most potent against multiple cancer cell lines (IC50 = 1.0 μM, MDA-MB-231). The compound 5k exhibited selective cytotoxicity against breast cancer cell line MCF7 (IC50 = 3.1 μM).