The diazonium salt derived from 4-amino-N,1,3-trimethyl-N-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1H-pyrazole-5-carboxamide (14) was reacted with a mixture of CuSO4 and NaCl, with ascorbic acid as an initiator to afford the planar derivative 4,6-dihydro-1,4,6,8-tetramethyl-3-phenyldipyrazolo[3,4-b:4′,3′-d]pyridin-5(3H)-one (16) and its unexpected isomer 4,6-dihydro-3,4,6,8-tetramethyl-1-phenyldipyrazolo[4,3-b:4′,3′-d]pyridin-5(1H)-one (17), as well as the epimers (3S,4S)- (or (3S,4R)-) and (3S,4R)- (or (3S,4S)-) 4-chloro-2,4-dihydro-1′,3′,5,5′-tetramethyl-2-phenylspiro[pyrazole-3,4′(1′H)-pyrrolo[3,4-c]pyrazol]-6′(5′H)-one (18a and b, respectively). Epimers 18a and b were converted under basic conditions to 4′-chloro-N,1,3,3′-tetramethyl-1′-phenyl-[4,5′-bi-1H-pyrazole]-5-carboxamide (19). The structures of isomers 16 and 17 determined by single-crystal X-ray analysis are also reported. Linear dichroism (LD) measurements for the above isomers suggest that 17 intercalates into DNA, and 17 exhibited antiproliferation activity against human NCI-H460 pulmonary carcinoma cells.
|Data di pubblicazione:||2005|
|Titolo:||Nonclassical Pschorr and Sandmeyer Reactions in Pyrazole Series|
|Autori:||MAGGIO, B; DAIDONE, G; RAFFA, D; PLESCIA, S; BOMBIERI, G; MENEGHETTI, F|
|Tipologia:||Articolo su rivista|
|Citazione:||MAGGIO, B., DAIDONE, G., RAFFA, D., PLESCIA, S., BOMBIERI, G., & MENEGHETTI, F. (2005). Nonclassical Pschorr and Sandmeyer Reactions in Pyrazole Series. HELVETICA CHIMICA ACTA, 88, 2272-2281.|
|Digital Object Identifier (DOI):||10.1002/hlca.200590161|
|Appare nelle tipologie:||01 - Articolo su rivista|