- Synthesis and biological evaluation of pyrroloiminoquinone derivatives
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Synthesis of 10 pyrroloiminoquinone derivatives is presented. The strategy is based around the elaboration of a common intermediate by reaction with primary amines. All the compounds obtained have been subjected to antiproliferative activity with three different cell lines (NCI-H460, HeLa, and HL-60). The capacity of 4 selected compounds to affect the enzymatic activity of the nuclear enzyme DNA topoisomerase II and to form the typical DNA fragmentation which occurs in the apoptotic process is discussed here.
- Passarella, Daniele,Belinghieri, Francesca,Scarpellini, Michele,Pratesi, Graziella,Zunino, Franco,Gia, Ornella Maria,Via, Lisa Dalla,Santoro, Giuseppe,Danieli, Bruno
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p. 2431 - 2438
(2008/09/21)
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- New synthetic approach to pyrroloiminoquinone marine alkaloids. Total synthesis of makaluvamines A, D, I, and K
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A new entry into pyrroloiminoquinone marine alkaloids, makaluvamines, has been developed. The key 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline intermediates 11 and 18 were prepared by aryne-mediated cyclization of the 4- chloro-6-methoxytryptamine derivatives 10 and 17, respectively. The requisite substituents at the indole 4- and 3-positions of 10 and 17 were efficiently assembled by sequential use of directed lithiation of 1-triisopropylsilyl-6- methoxygramine (6) and fluoride ion-induced elimination-addition of the methiodide of 4-chloro-l-triisopropylsilyl-6-methoxygramine (7) as key reactions.
- Iwao, Masatomo,Motoi, Osamu,Fukuda, Tsutomu,Ishibashi, Fumito
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p. 8999 - 9010
(2007/10/03)
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