Formylation of a metathesis-derivedansa[4]-ferrocene: a simple route to anticancer organometallics

Abstract

<p> <italic>Ansa</italic>-Ferrocenealdehyde, obtained by formylation of a metathesis-derived <italic>ansa</italic>-ferrocene, was transformed into a conjugate with triazole and uracil with anticancer activity.</p>

N‐Allyl‐N‐ferrocenylmethylamines andansa‐Ferrocenylmethylamines: Synthesis, Structure, and Biological Evaluation

“…The cytotoxic effects of the most active compounds determined in this study are comparable to those of ferrocene‐organic hybrids, such as ferrocene‐modified nucleobases [24] or ferrocene‐triazole‐uracil conjugates [16,25] . On the other hand, the tamoxifen‐derived ferrocifen family displays antitumour activity in the nanomolar range [26] .…”

“…The tested compounds do not include a known cytotoxic functional group, yet the activity is comparable to the related uracil-triazole-ferrocene conjugates. [16] Preliminary cell cycle progression studies suggest the effect of ansa-4 on cell cycle progression, resulting in the prolongation of S-phase (DNA replication). Considering that cancer cells are characterized by genetic instability and proliferation, this mechanism of action could be considered as promising, although it requires further in-depth research.…”

“…The cytotoxic effects of the most active compounds determined in this study are comparable to those of ferroceneorganic hybrids, such as ferrocene-modified nucleobases [24] or ferrocene-triazole-uracil conjugates. [16,25] On the other hand, the tamoxifen-derived ferrocifen family displays antitumour activity in the nanomolar range. [26] Similarly, strongly cytotoxic ferrocenyl amino phosphines with IC 50 = 6.9 μg mL À 1 against HT1376 cells, or IC 50 < 5 μg mL À 1 against Hep3B cells, have been reported.…”

A Review on Olefin Metathesis Reactions as a Green Method for the Synthesis of Organic Compounds

“…is type of reaction is now being used in drug discovery for the synthesis of anticancer and other antibiotic organic compounds. Mazur et al discovered a novel drug, the ansaferrocene-triazole-uracil conjugate, (±)-9 for the relief of breast cancer through metathesis reactions using 1,1′-diallylferrocene (1) as a starting material through ring-closing metathesis and other consecutive reactions in the presence of Grubbs catalysts (Schemes 3(a)-3(c)) [14].…”

Synthesis and biological evaluations of mono‐ and bis‐ferrocene uracil derivatives

“…[20] Furthermore, ferrocene tagged multi-functionalized 1,4-dihydropyrimidines displayed inhibitory activity against human breast cancer cells equal to doxorubicin. [21] The anticancer potential of organometallic nucleoside analogs via the synthesis of ferrocene-nucleobase conjugates was explored [21][22][23][24][25][26][27][28][29][30][31][32] and recently showed that the introduction of a bulky and lipophilic ferrocenylmethylene-ferrocenyl (Fc-CH 2 -Fc) moiety improved the activities compared to that of the single metallocenecontaining compounds. [33] Ferrocenyl alkyl thymine in combined application in vivo with anticancer drug cyclophosphamide demonstrated therapeutic synergism against Lewis lung carcinoma (LLC).…”