Administration of ferrocene‐modified amino acids induces changes in synaptic transmission in the CA1 area of the hippocampus

Abstract

A series of ferrocene‐modified amino acid methyl esters with pyrazole linker was prepared in good to quantitative yields starting from easy accessible ferrocene pyrazole carbaldehyde and amino acids in racemic and enantio enriched forms under reductive amination conditions (NaBH (OAc)3, reflux, 3 hr). The resulting enantiomers were resolved using analytical HPLC on modified cellulose or amylose as chiral selectors. In vivo electrophysiological experiments were performed in the CA1 field of the hippocampus on 3a Fc‐Gly, (L)‐3b Fc‐Ala, and (D)‐3b Fc‐Ala compounds. An increasing in the amplitudes of responses of local potentials (up to 25%) of the CA1 region in the studied groups was found after intraperitoneal administration of ferrocene compounds 3a and (D)‐3b compared with control rats treated with saline.

Ferrocene‐modified imidazoles: One‐pot oxalyl chloride‐assisted synthesis, HPLC enantiomeric resolution, and in vivo antitumor effects

“…So, on the example of ferrocene-based L-and S C H E M E 1 Some previously published synthetic approaches to ferrocenylalkyl imidazoles (in square brackets are given references) D-alanine, differences in the electrophysiological effect on the hippocampus are shown. [45] Sometimes the bioeffects are equally positive, sometimes opposite. Since the thalidomide tragedy, the pharmacopoeias of most countries and the European community have required that potential drug candidates, if they represent racemic mixtures, should be investigated for each individual enantiomer.…”

Application of capillary electrophoresis technique for the enantioseparation of bioactive ferrocene‐based compounds versus DFT calculated data

“…In spite of the fact that modern ferrocene chemistry is extensively developing, especially in the field of medicine, biological examinations of chiral ferrocene‐based individual stereoisomers are currently limited, excluding the ferrocene‐based compound named ferroquine that undergoes clinical trials as an antimalarial agent [16], ferrocene‐hormones for specific receptors [17], and ferrocene‐thymine conjugates, which can be used as potential anticancer agents [18]. Recently, primary electrophysiological studies of ferrocene‐modified amino acids, including ferrocene derivatives of d ‐ and l ‐alanine, were carried out in vivo on the hippocampus and demonstrated different effects for both stereoisomers [19]. It is appropriate, as only example of the industrial use of the enantiomeric enriched ferrocene‐based compound, to mention the Ugi's amine, ( R )‐FcCH(CH 3 )N(CH 3 ) 2 [20].…”

The nature of ferrocenylalkylating agent in the acid-catalyzed reactions with ferrocenyl(phenyl)methanol

“…The result was the introduction into clinical practice of Ferrocerone, the only ferrocene-based drug for the treat-ment of iron defi ciency anemia and periodontal disease. 23, 24 Later, such types of biological activity as antitumor, 7,10,21-23 antibacterial, 24 antimalarial, 25 and many others [26][27][28][29][30][31][32][33][34][35] were revealed. Methods for the synthesis of ferrocene derivatives of heterocycles are constantly being improved, 36 however, only ferrocenylmethyl and ferrocenylethyl derivatives have been widely studied.…”