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1.
J Org Chem ; 73(13): 4771-82, 2008 Jul 04.
Article in English | MEDLINE | ID: mdl-18396906

ABSTRACT

Binding of inorganic anions, carboxylic acids, and tetraalkylammonium carboxylates by macrocyclic compounds of different size was studied by NMR in DMSO-d6. It has been shown that at least a 15-membered ring is necessary for successful recognition of fluoride. Larger macrocycles were shown to bind HSO4(-), H2PO4(-), Cl(-), and carboxylic acid salts. Effects of binding topicity are discussed. The 30-membered macrocycles 4 and 4m selectively bind substrates that are size- and shape-complementary: maximum binding is observed for dicarboxylic acids and dicarboxylates with four-carbon chains, and the binding constant for association of fumaric acid and 4 is ca. 5 orders of magnitude higher than that of maleic acid. The 30-membered macrocycle 4m showed selectivity toward alpha-ketocarboxylic acids. Secondary amino groups were not crucial for binding of fluoride to the macrocycles; however, they proved to be very important for selectivity and strength of carboxylic acid binding. The X-ray structure of the adduct of 4 and nitrobenzoic acid confirmed the guest H-bonding with both the amide and the secondary amino groups of the 30-membered macrocyclic host.


Subject(s)
Aminopyrine/chemical synthesis , Carboxylic Acids/chemistry , Macrocyclic Compounds/chemical synthesis , Anions , Models, Molecular , Molecular Structure
2.
Molecules ; 11(11): 904-14, 2006 Nov 17.
Article in English | MEDLINE | ID: mdl-18007395

ABSTRACT

The synthesis of Cu(II) complexes derived from Schiff base ligands obtained by the condensation of 2-hydroxybenzaldehyde or terephtalic aldehyde with 4-amino-antipyrine (4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one) is presented. The newly prepared compounds were characterized by( 1)H-NMR, UV-VIS, IR and ESR spectroscopy. The determination of the antimicrobial activity of the ligands and of the complexes was carried out on samples of Escherichia coli, Klebsiella pneumoniae, Acinetobacter boumanii, Pseudomonas aeruginosa, Staphylococcus aureus and Candida sp. The qualitative and quantitative antimicrobial activity test results proved that all the prepared complexes are very active, especially against samples of Ps. aeruginosa, A. Boumanii, E. coli and S. aureus.


Subject(s)
Aminopyrine/analogs & derivatives , Copper/chemistry , Aminopyrine/chemical synthesis , Aminopyrine/chemistry , Aminopyrine/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Differential Thermal Analysis , Diffusion , Electron Spin Resonance Spectroscopy , Ligands , Microbial Sensitivity Tests , Spectrophotometry, Infrared , Temperature , Thermogravimetry
3.
J Med Chem ; 46(8): 1531-7, 2003 Apr 10.
Article in English | MEDLINE | ID: mdl-12672254

ABSTRACT

A series of 13 new (S,Z)-2-aminopurine methylenecyclopropane analogues was synthesized, and their antiviral activity was investigated. The nucleophilic displacement of chlorine of 2-amino-6-chloropurine derivative 5 with allyl-, propargyl-, cyclopropylmethyl-, isopropyl-, benzyl-, cyclohexyl-, and 2-hydroxyethylamine gave N(6)-alkyl compounds 2a, 2b, 2c, 2d, 2e,2f, and 2g. A similar reaction of 5 with allyl, cyclopropylmethyl, propyl, or pentyl alcohol catalyzed by K(2)CO(3) afforded O(6)-alkyl analogues 3a, 3c, 3h and 3i. Propane- and pentanethiol furnished S(6)-alkyl compounds 4h and 4i. The N(6)-alkyl derivatives 2a, 2b, O(6) analogues 3a, 3c, 3h, 3i, and S(6) compounds 4h, 4i which were highly effective in all CMV assays and exhibited the lowest cytotoxicity in proliferating HFF cells appear to be good candidates for in vivo assays. Activity of new analogues against HSV-1 or HSV-2 was restricted to BSC-1 and Vero cultures. Compounds 2c, 2b, 3a and 3h were effective against EBV in one of two assays (Daudi or H-1). Analogues 3a and 4i were the most active anti-VZV agents whereas compounds 3h, 3i, and 4h inhibited the replication of HBV in a micromolar concentration range.


Subject(s)
Aminopyrine/analogs & derivatives , Aminopyrine/chemical synthesis , Antiviral Agents/chemical synthesis , Cyclopropanes/chemical synthesis , Hepatitis B virus/drug effects , Herpesviridae/drug effects , Purine Nucleosides/chemical synthesis , Aminopyrine/chemistry , Aminopyrine/pharmacology , Animals , Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Cell Line , Chlorocebus aethiops , Cyclopropanes/chemistry , Cyclopropanes/pharmacology , Enzyme-Linked Immunosorbent Assay , Humans , Mice , Purine Nucleosides/chemistry , Purine Nucleosides/pharmacology , Stereoisomerism , Structure-Activity Relationship , Viral Plaque Assay
5.
Pharmazie ; 34(2): 70-3, 1979.
Article in English | MEDLINE | ID: mdl-441108

ABSTRACT

Synthesis of four different series of compounds having the phenazone moitety was accomplished, in the hope that one or more of the prepared compounds might possess pharmacological activity. These compounds may contain a hydrazone, an acid hydrazide, certain basic residues, or disubstituted urea structure.


Subject(s)
Aminopyrine/analogs & derivatives , Aminopyrine/chemical synthesis , Aminopyrine/pharmacology , Analgesics/chemical synthesis , Animals , Anti-Inflammatory Agents/chemical synthesis , Hydrazines/chemical synthesis , Hydrazines/pharmacology , Hydrazones/chemical synthesis , Hydrazones/pharmacology , Rats
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