o‐Carboxybenzoylferrocene. Bioactivity and chemical Modifications

Abstract

The antitumor activity of o-carboxybenzoylferrocene sodium salt (1) was studied in vivo. Interaction between o-carboxybenzoylferrocene (2) and N,N -carbonyldiimidazole in boiling methylene dichloride leads to 3-(N-imidazolyl)-3-ferrocenylisobenzofuran-1(3H)-one (5). The structure of compound 5 was established by X-ray analysis. Aminolysis of compound 5 in toluene gave rise to ferrocenoylbenzamides (6a-d)-derivatives of dimethylamine, piperidine, pyrrolidine and morpholine.

Antimalarial, Anti-trypanosomiasis, Anti-HIV and Cytotoxicity Studies of Some Ferrocenyl Schiff bases

“…All the compounds (1-12) showed low toxicity because %cell viability was above 50%. This is not surprising because it had earlier been reported that ferrocenyl derived compounds do possess low toxicity [46]- [48]. …”

Synthesis and crystal structures of 2-(ferrocenylcarbonyl)benzoic acid and 3-ferrocenylphthalide

“…The carbonyl carbon, C11 in compound 1 bends toward the iron center with a distance of 0.163 (3) from the leastsquares plane of the substituted Cp while the corresponding C11 atom in compound 2 bends slightly outward with a distance of 0.117 (4) Å from the plane of Cp. Similar bending can be seen in the N-imidazolyl derivative of compound 2 (Simenel et al, 2008). The carbonyl carbon in compound 1 lies roughly in the same plane as the substituted Cp with a torsional angle C2-C1-C11-O1 of 2.9 (2) .…”

Simple route to ferrocenylalkyl nucleobases. Antitumor activity in vivo

“…As seen from Table 1, carcinoma 755 is considerably more sensitive to compound 1 than Lewis lung carcinoma. This phenomenon was noted early 20, 22. The maximum level of the tumor growth inhibition, 70% as compared with controls, was observed after administration of compound 1 in the dose 2.5 mg kg −1 .…”

“…Thus, compound 1 exhibited maximum antitumor effect (carcinoma 755) at small doses. Such an inverse dose–effect response was found early for ferrocenylmethyl benzimidazole20a (Lewis lung carcinoma, dose 5.0 mg kg −1 , tumor growth inhibition 70%), ortho ‐carboxybenzoylferrocene sodium salt22 (carcinoma 755, dose 2.5 mg kg −1 , tumor growth inhibition 70%) and the other ferrocene derivatives 20c. Apparently, the found dose–efficiency dependence—the achievement of the maximum antitumor effect after application of the agent in the rather low doses—is typical for ferrocene compounds of this kind.…”

“…Antitumor effects of ferrocene compounds are well known 3. The activities were found for positively charged ferricenium salts,19, 20 uncharged ferrocene derivatives,20 potentially anionogenic Fc‐compounds21 and compounds with negative charge22 as well. The further development of these investigations included modification of ferrocene compounds by some cytostatic drugs and vitamins (sarcolysin,23 cisplatin,24 tamoxifen,5, 25 thiamin and hydroxythiamine26), as well as the synthesis of new original compounds.…”