849939-22-6Relevant articles and documents
The pyrrole approach toward the synthesis of fully functionalized cup-shaped molecules
Zonta, Cristiano,Fabris, Fabrizio,De Lucchi, Ottorino
, p. 1003 - 1006 (2005)
(Chemical Equation Presented) A novel method for the synthesis of new highly functionalized cyclotrimers is described. The method consists of an original synthesis of β-dibromosubstituted pyrroles, metalation, cycloaddition, and cyclotrimerization. The se
Synthesis of a novel benzocyclotrimer with one rigid and one flexible electron-rich cavity
Bolzan, Alceste,Bortoluzzi, Marco,Borsato, Giuseppe,Fabbro, Chiara,Da?tan, Arif,De Lucchi, Ottorino,Fabris, Fabrizio
, p. 1067 - 1074 (2015)
The straightforward synthesis of a novel benzocyclotrimer is herein presented. The syn-product is characterized by an electron-rich rigid aromatic cavity and a flexible electron-rich aromatic pocket. The molecule is a potential scaffold for supramolecular
A facile synthesis of diaryl pyrroles led to the discovery of potent colchicine site antimitotic agents
Romagnoli, Romeo,Oliva, Paola,Salvador, Maria Kimatrai,Manfredini, Stefano,Padroni, Chiara,Brancale, Andrea,Ferla, Salvatore,Hamel, Ernest,Ronca, Roberto,Maccarinelli, Federica,Rruga, Fatlum,Mariotto, Elena,Viola, Giampietro,Bortolozzi, Roberta
, (2021/02/09)
Three different series of cis-restricted analogues of combretastatin A-4 (CA-4), corresponding to thirty-nine molecules that contained a pyrrole nucleus interposed between the two aryl rings, were prepared by a palladium-mediated coupling approach and evaluated for their antiproliferative activity against six human cancer cell lines. In the two series of 1,2-diaryl pyrrole derivatives, results suggested that the presence of the 3′,4′,5′-trimethoxyphenyl moiety at the N-1 position of the pyrrole ring was more favorable for antiproliferative activity. In the series of 3,4-diarylpyrrole analogues, three compounds (11i-k) exhibited maximal antiproliferative activity, showing excellent antiproliferative activity against the CA-4 resistant HT-29 cells. Inhibition of tubulin polymerization of selected 1,2 pyrrole derivatives (9a, 9c, 9o and 10a) was similar to that observed with CA-4, while the isomeric 3,4-pyrrole analogues 11i-k were generally from 1.5- to 2-fold more active than CA-4. Compounds 11j and 11k were the only compounds that showed activity as inhibitors of colchicine binding comparable to that CA-4. Compound 11j had biological properties consistent with its intracellular target being tubulin. This compound was able to block the cell cycle in metaphase and to induce significant apoptosis at a concentration of 25 nM, following the mitochondrial pathway, with low toxicity for normal cells. More importantly, compound 11j exerted activity in vivo superior to that of CA-4P, being able to significantly reduce tumor growth in a syngeneic murine tumor model even at the lower dose tested (5.0 mg/kg).
3,4-Ferrocenyl-functionalized pyrroles: Synthesis, structure, and (spectro)electrochemical studies
Korb, Marcus,Pfaff, Ulrike,Hildebrandt, Alexander,Rüffer, Tobias,Lang, Heinrich
, p. 1051 - 1061 (2014/03/21)
The synthesis of 3,4-diferrocenyl-substituted pyrroles of the type 3,4-Fc2-cC4H2NR [Fc = Fe(η5- C5H4)(η5-C5H5); R = Ph (3a), SO2-4-MeC6/sub
3,4-ferrocenyl-functionalized pyrroles: Synthesis, structure, and (spectro)electrochemical studies
Korb, Marcus,Pfaff, Ulrike,Hildebrandt, Alexander,Rüffer, Tobias,Lang, Heinrich
, p. 1051 - 1061 (2015/04/27)
The synthesis of 3,4-diferrocenyl-substituted pyrroles of the type 3,4-Fc2-cC4H2NR [Fc = Fe(η5-C5H4)(η5-C5H5); R = Ph (3a), SO2-4-MeC6
