Synthesis of complex compounds of methyl derivatives of 8-quinolineselenol with metals and their cytotoxic activity

A series of 2-methyl-, 4-methyl-, and 2,4-dimethyl-8-quinolineselenolates of zinc, cadmium, mercury, nickel, palladium, platinum, arsenic, antimony, and bismuth has been synthesized and their cytotoxicity has been studied on HT-1080 (human fibrosarcoma), MG-22A (mouse hepatoma), B16 (mouse melanoma), and Neuro 2A (mouse neuroblastoma) tumor cells. Mercury complexes were distinguished by high cytotoxicity on all the cell lines. Palladium complexes possessed somewhat lower activity and were significantly less toxic in relation to normal NIH 3T3 mouse embryo fibroblasts. All the studied metal 2-methyl-8-quinolineselenolates displayed high cytotoxicity on B16 melanoma, arsenic 4-methyl-8-quinolineselenolate acted most effectively on HT-1080 and MG-22A cells. Di(4-methyl-8-quinolyl) diselenide also possessed high cytotoxicity on these same cells. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 59–66, January, 2006.     

Pb(II) and Cd(II) Tetrafluoroborate Complexes with Nitrogen-Containing Organic Bases. HSAB Concept

Comparative analysis of the calculated values of the equalized electronegativity, polarity, hardness (softness) of the coordination bond, and the effective charges of the metal atoms in Pb and Cd tetrafluoroborate complexes with nitrogen-containing bases was performed. The above characteristics were shown to depend on the electron-donor properties of the starting organic ligands. It was shown that an increase in the organic base hardness brings about an increase in hardness of the metal–ligand bond in a complex.     

Synthesis and cytotoxic properties of 7α-chloro-3-methyl-1,1-dioxoceph-3-ems, substituted with amide or keto group at position 4

7α-Chloro-3-methyl-1,1-dioxoceph-3-ems with amide or keto group at position 4 have been synthesized by structural modification of 7α-chloro-3-methyl-1,1-dioxoceph-3-em-4-carboxylic acid. Screening of these compounds for cytotoxic activity revealed compounds with specific activity against cancer cells in vitro, capable of effective inhibition of the growth of sarcoma S-180 in vivo. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, 1849–1859, December 2007.     

Synthesis and hydroxydeamination in the series of 6-aryl- and 6-benzoimidazolyl-7-aminoazolo[5,1-c]-1,2,4-triazines

The replacement of the amino group with the hydroxy group was examined in the series of 6-aryl- and 6-benzoimidazolyl-7-aminoazolo[5,1-c]-1,2,4-triazines. These reactions provide a convenient synthetic procedure for the preparation of fused azolo[5,1-c]-1,2,4-triazin-7-ones.     

A new method for generating organosilanones

A new method for the generation of organosilanones by the reaction of betaines, R₃P⁺-CR¹R²-SiR³R⁴-S^–, with (Et₃Sn)₂O was suggested.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2246–2247, December, 1994.This study was financially supported by the Russian Foundation for Basic Research, Project No. 94-03-09710.     

On the Problem of the Tetrafluoroborate Ion State in Complexes with Nitrogen-Containing Organic Bases

Using a number of Cu(II), Zn(II), and Cd(II) tetrafluoroborate complexes with nitrogen-containing organic bases as examples, the possible existence of two states of the BF₄ ^– ion, namely, the "half-coordination" and counter-ion states, was studied. It was found that in [ML₂(BF₄)₂] complexes with strong organic bases (L), the "half-coordination" of the anion exists. As the electron-donating ability of the ligand increases, the interaction between the tetrafluoroborate ion and the metal atom becomes more efficient.     

Synthesis and cytotoxic activity of derivatives of the <Emphasis Type="Italic">tert</Emphasis>-butyl ester of 7<Emphasis Type="Italic">Z</Emphasis>-acetylmethylene-3-methyl-3-cephem-4-carboxylic acid

The condensation of the acetylmethylene group in the tert-butyl esters of 7Z-acetylmethylene-3-methyl-3-cephem-4-carboxylic acid and 7Z-acetylmethylene-3-methyl-1,1-dioxo-3-cephem-4-carboxylic acid and in 7Z-acetylmethylene-3-methylene-1,1-dioxo-3-cephem with arylmethoxyamines and O-alkylation of the tert-butyl ester of 7Z-(2-hydroxyimino)propylidene-3-methyl-1,1-dioxo-3-cephem-4-carboxylic acid using substituted benzyl bromides as well as pyridylmethyl chlorides gave arylmethoxyimino and pyridylmethoxyimino derivatives of these compounds in the syn and anti isomeric forms. The Vilsmaier reagent was used to introduce the N,N-dimethylaminomethylene group at C-2 of the cephem system in the tert-butyl esters of 7Z-[2-(arylmethoxyimino)propylidene]-3-methyl-1,1-dioxo-3-cephem-4-carboxylic acid. Subsequent transformation of the N,N-dimethylaminomethylene cephems using hydroxylamine led to 3Z-[2-(anti-arylmethoxyimino)propylidene]-tert-butoxycarbonylmethyl-4-(5-methyl-4-isoxazolylsulfonyl)- azetidin-2-ones. Condensation of the acetyl group in the tert-butyl ester of 7Z-acetylmethylene- 3-methyl-1,1-dioxo-3-cephem-4-carboxylic acid with 4-bromophenylhydrazine gave a cephem with a 2-(4-bromophenylhydrazono)propylidene group at C-7. Acylation of the tert-butyl ester of 7Z-(2-hydroxyimino)propylidene-3-methyl-1,1-dioxo-3-cephem-4-carboxylic acid by 2-bromobenzoyl chloride gave a cephem with a 2-(2-bromo-benzoyloxyimino)propylidene group at C-7. Biological screening of these products towards to malignant and normal cells in vitro showed that their antitumor activity and cytotoxic selectivity towards to malignant and normal cells depend on the structure and configuration of the arylmethoxyimino and pyridylmethoxyimino groups in the 7-alkylidene substituent as well as on the presence or absence of N,N-dimethylaminomethylene and carboxyl groups, respectively, at C-2 and C-4 of the cephem system.     

Synthesis and biological activity of new 2-[(3-aminopropyl)dimethyl-silyl]-5-trialkylgermylfurans

New highly cytotoxic 3-aminopropyl derivatives of 2-dimethylsilyl-5-trialkylgermylfuran (IC₅₀ 1−3 μg⋅ml⁻¹) have been prepared by hydrosilylation of heterocyclic N-allylamines with the corresponding hydrosilane in the presence of Speier’s catalyst. The influence of the amine structure and alkyl substituent at the germanium atom on the cytotoxicity has been investigated.     

Synthesis of novel [1-aziridinyl-(hydroxyimino)methyl]arenes and their cytotoxic activity

The synthesis has been developed for novel potential anticancer agents whose structures contain an aziridine amidoxime group. The cytotoxic activity of all of the target compounds on different cell lines are given together with the in vitro IC₅₀ and LD₅₀ values found. The most promising anticancer agents were found to be the methyl 4-[1-aziridinyl(hydroxyimino)methyl]benzoate, 1-aziridinyl(2-naphthyl)-methanone oxime, and 1-aziridinyl(2-quinolyl)methanone oxime. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 203–213, February, 2009.