An efficient multicomponent reaction of arenealdehydes, mercaptoacetic acid and piperonilamine under ultrasound irradiation to afford 2-aryl-3-(piperonylmethyl)-1,3-thiazolidin-4-ones is reported. Applying this methodology, eleven heterocycles were synthesized and isolated in good yields after short reaction times.
Fifteen 7-chloro-4-arylhydrazonequinolines have been evaluated for their in vitro antifungal activity against eight oral fungi: Candida albicans, C. parapsilosis, C. lipolytica, C. tropicalis, C. famata, C. glabrata, Rhodutorula mucilaginosa, and R. glutinis. Several compounds exhibited minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) activities comparable with the first-line drug fluconazole. These results could be considered as an important starting point for the rational design of new antifungal agents.
The title compound, C11H14N4O4, is essentially planar with an r.m.s. deviation for the 19 non-H atoms of 0.152 Å. The conformation about the C=N bond is E, and the molecule has a U-shape as the butyl group folds over towards the aromatic system. An intramolecular C—H⋯N interaction occurs. The crystal packing is dominated by N—H⋯O hydrogen bonding and C—H⋯O contacts, leading to twisted zigzag supramolecular chains along the c direction. The crystal packing brings two nitro O atoms into an unusually close proximity of 2.686 (4) Å. While the nature of this interaction is not obvious, there are several precendents for such short nitro–nitro O⋯O contacts of less than 2.70 Å in the crystallographic literature.
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