First macrocycle based on chlorin and isosteviol structural elements

Acylation by suberic acid chloride of chlorin with two oximated isosteviol groups on its periphery produced for the first time a macrocyclic system containing a porphyrin ring and two tetracyclic ent-beyerane frameworks.     

Alkylation of the isosteviol terpenoid and its oxime with dibromoalkanes in the KOH-DMSO system

The reaction of 16-hydroximinoisosteviol with dihaloalkanes in the KOH-DMSO results in coupling of two isosteviol carcasses by the carboxy groups. The same products were previously synthesized by hydroximination of isosteviol diesters.     

Chemistry and Structure of Diterpene Compounds of the Kaurane Series: VII. Chiral Complexes of Isosteviol with Aromatic Compounds

(4,8,13)-13-Methyl-16-oxo-17-norkaurane-18-carboxylic acid (isosteviol) forms with aniline, dimethylaniline, and toluene individual 2:1 molecular complexes whose crystals are isostructural. According to X-ray diffraction data, the supramolecular crystal structure of these complexes is formed by chiral double helices with a 4₃ screw axis, consisting of isosteviol molecules. The strands of the helices are linked together by intermolecular hydrogen bonds involving the carboxy and carbonyl groups of two isosteviol molecules of neighboring helices. In their turn, the two hydrogen-bonded isosteviol molecules form head-to-tail pseudocage dimers. The aromatic guests occupy fairly large cavities between the strands of isosteviol helices.     

Conformation of 1,5-Bis(16-oxobeyeran-19-oyloxy)-3-oxapentane in CCl<Subscript>4</Subscript>

1,5-Bis(16-oxobeyeran-19-oyloxy)-3-oxapentane in carbon tetrachloride exists mainly in tweezers-like conformations where the isosteviol fragments hang over each other.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 2, 2005, pp. 272–275.Original Russian Text Copyright © 2005 by Kataev, Strobykin, Timosheva, Al’fonsov, Korochkina, Strobykina.     

Synthesis and antimicrobial activity of several bis-quaternized ammonium derivatives of the diterpenoid isosteviol

Previously unreported bis-quaternized ammonium derivatives of the diterpenoid isosteviol (16-oxo-entbeyeran-19-oic acid) were synthesized. The compound in which the two quaternized N atoms were joined by a dodecamethylene spacer had the greatest antimicrobial activity and was comparable in activity with ciprofloxacin and clotrimazole.     

Chemistry and Structure of Diterpene Derivatives of the Kaurane Series: V. Isosteviol Anhydrides

(4,8,13)-13-Methyl-16-oxo-17-norkaurane-18-carboxylic acid (isosteviol) anhydride is synthesized, which is a first representative of bisditerpene compounds of the kaurane series. The structures of the anhydride and isosteviol chloride were studies by X-ray diffraction and quantum chemistry (AM1).     

Isosteviol and some of its derivatives as receptors and carriers of amino acid picrates

The ability of diterpenoid isosteviol 1 (ent-16-oxobeyeran-19-oic acid) and some of its derivatives with ester and amide groups to bind amino acid picrates in the course of their transport through a liquid chloroform membrane was observed for the first time. Isosteviol was very competitive with dibenzo-18-crown-6 and N,N′-bis(isostevioyl)-1,4-phenylenediamine 5 was even more effective in transportation of d,l-tryptophan through a liquid chloroform membrane.     

Chemistry and Structure of Diterpenoids: X. Isosteviol Amides

Acylation of amino alcohols with isosteviol chloride, depending on the reactant ratio, leads to formation of either bis-isosteviol derivatives or N-acylation products. Reactions of aromatic diamines with 2 equiv of isosteviol chloride give the corresponding N,N′-bis(isostevioyl) derivatives.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 2, 2005, pp. 276–281.Original Russian Text Copyright © 2005 by Al’fonsov, Kataev, Strobykina, Korochkina, Kovylyaeva, Bakaleinik, Beskrovnyi, Gubaidullin, Litvinov, Musin.For communication IX, see [1].     

Investigation of diterpenoid isosteviol ammonium derivatives by matrix-assisted laser desorption/ionization mass spectrometry

Matrix-assisted laser desorption/ionization (MALDI) mass spectra of diterpenoid isosteviol ammonium derivatives have been analyzed. The compounds were synthesized as antibacterial agents. It has been found that peaks of salt cations were detected in positive ion MALDI mass spectra of mono-quaternary derivatives. The fragmentation of bis-quaternary salts depended on the distance between the ammonium centers. Clusters containing dication and acidic matrix anion have been observed for compounds with two quaternized nitrogen atoms connected by a nonanomethylene or a longer spacer. Similar clusters did not form for compounds containing pentamethylene or a shorter spacer between two quaternized nitrogen atoms.