5376-10-3Relevant academic research and scientific papers
Monomers and polymers carrying imidazole and benzimidazole groupings, and proton exchange membrane containing the same for the production of a fuel cell
-
Page/Page column 6, (2014/10/28)
The invention relates to a monomer (6, 14) carrying an imidazole-type heterocycle (3). According to the invention, the chemical structure of said monomer (6, 14) comprises at least one unit of formula (I) wherein R1 comprises an alkenyl grouping and R2 comprises a grouping for protecting one of the nitrogen atoms of the heterocycle. The invention also relates to a monomer carrying a benzimidazole-type heterocycle, and to protected polymers obtained from said monomers, deprotected polymers produced by the protected polymers, a proton exchange membrane based on deprotected polymers, and a fuel cell provided with said membrane. Furthermore, the invention relates to methods for producing the above-mentioned monomers and polymers.
Synthesis and antimicrobial profile of N-substituted imidazolium oximes and their monoquaternary salts against multidrug resistant bacteria
Od?ak, Renata,Sko?ibu?i?, Mirjana,Maravi?, Ana
, p. 7499 - 7506 (2013/11/19)
Two different series of N-substituted imidazolium oximes and their monoquaternary salts were synthesized and biologically tested with respect to their ability to inhibit growth a diverse panel of antibiotic susceptible Gram-positive and antibiotic resistant Gram-negative bacteria as well fungal strains. The newly synthesized compounds were analyzed by spectral studies to confirm their structure. The preliminary results showed that all compounds tested possess promising antimicrobial potential against both susceptible Gram-positive and antibiotic resistant Gram-negative isolates, exhibiting a wide range of MIC values from 0.14 to 100.0 μg/mL. The structure-activity relationship demonstrates that the p-methylphenyl and p-fluorophenyl groups in monoquaternary salts 6 and 7 attached directly to the imidazolium ring could be essential for observed remarkable inhibitory profiles against clinically important pathogens Pseudomonas aeruginosa (MIC = 0.14 μg/mL) and Klebsiella pneumoniae (MIC = 1.56 μg/mL). Furthermore, the broth microdilution assay was then used to investigate the antiresistance efficacy of compound 7 against fourteen extended-spectrum β-lactamase (ESBL)-producing strains in comparison to eight clinically relevant antibiotics. Compound 7 exhibited a remarkable antiresistance profiles ranging between 0.39 and 12.50 μg/mL against all of ESBL-producing strains, which leads to the suggestion that may be interesting candidate for development of new antimicrobials to combat multidrug resistant Gram-negative bacteria.
Syntheses, protonation constants and antimicrobial activity of 2-substituted N-alkylimidazole derivatives
Kleyi, Phumelele,Walmsley, Ryan S.,Gundhla, Isaac Z.,Walmsley, Tara A.,Jauka, Tembisa I.,Dames, Joanna,Walker, Roderick B.,Torto, Nelson,Tshentu, Zenixole R.
, p. 231 - 238 (2013/01/15)
A series of N-alkylimidazole-2-carboxylic acid, N-alkylimidazole-2- carboxaldehyde and N-alkylimidazole-2-methanol derivatives [alkyl = benzyl, methyl, ethyl, propyl, butyl, heptyl, octyl and decyl] have been synthesized and the protonation constants determined. The antimicrobial properties of the compounds were tested against Gram-negative (Escherichi coli), Gram-positive (Staphylococcus aureus & Bacillus subtilis subsp. spizizenii) bacterial strains and yeast (C. albicans). Both the disk diffusion and broth microdilution methods for testing the antimicrobial activity showed that N-alkylation of imidazole with longer alkyl chains and the substitution with low pKa group at 2-position resulted in enhanced antimicrobial activity. Particularly, the N-alkylimidazole-2-carboxylic acids exhibited the best antimicrobial activity due to the low pKa of the carboxylic acid moiety. Generally, all the N-alkylimidazole derivatives were most active against the Gram-positive bacteria [S. aureus (MIC = 5-160 μg mL-1) and B. subtilis subsp. spizizenii (5-20 μg mL-1)], with the latter more susceptible. All the compounds showed poor antimicrobial activity against both Gram-negative (E. coli, MIC = 0.15 to >2500 μg mL-1) bacteria and all the compounds were inactive against the yeast (Candida albicans).
MUSCARINIC RECEPTOR ANTAGONISTS
-
Page/Page column 8, (2010/06/19)
The present invention generally relates to muscarinic receptor antagonists of formula I, which are useful, among other uses, for the treatment of various diseases of the respiratory, urinary and gastrointestinal systems mediated through muscarinic receptors. The invention also relates to the process for the preparation of disclosed compounds, pharmaceutical compositions containing the disclosed compounds, and the methods for treating diseases mediated through muscarinic receptors. Formula (I) wherein Het: is heterocyclyl or heteroaryl X: O, S or NR1 and the other substituents are defined as in the claims.
Synthesis and properties of new fluorinated polymers bearing pendant imidazole groups for fuel cell membranes operating over a broad relative humidity range
Frutsaert, Guillaume,Delon, Louis,David, Ghislain,Ameduri, Bruno,Jones, Deborah J.,Glipa, Xavier,Roziere, Jacques
experimental part, p. 223 - 231 (2010/11/04)
New alternating copolymers comprising a chlorotrifluorinated backbone and midazole-terminated pendant ethylene oxide groups have been prepared with a view to their use as a component of proton-conducting membranes in polymer electrolyte fuel cells. A vinyl ether containing an imidazole (Imi) function protected by a benzyl group (BVI) was first synthesized in a three-step reaction. It was then copolymerlzed in solution with chlorotrifluoroethylene (CTFE) by conventional radical copolymerization leading to alternating poly(BVI-altCTFE) copolymers in good yields. Deprotection of the benzyl group under hydrogen produced a chlorotrifluorinated poly (Imi-alt-CTFE) copolymer. The polymer was subsequently used to form blend membranes with sulfonated poly(ether ether ke-tone) (sPEEK). The conductivity of blend membranes of poly (Imi-alt-CTFE) with sPEEK lies in the range of 4-10 mS cm-1 at 40-70 °C and, for blend membranes rich in poly(Imi-alt-CTFE), is little dependent on relative humidity between 30 and 100%. It Is surmised that the polymer and membrane composition favor microstructural phase separation into chlorotrifluorlnated polymer backbone domains and regions in which imidazole groups are clustered.
1-SUBSTITUTED-2-(N-PHENYL-N-(PHENYL-METHYL)METHANAMINE)-4,5-DIHYDRO-IMIDAZOLES AND RELATED COMPOUNDS AND THEIR USE IN TREATING CALCIUM OVERLOAD IN BRAIN CELLS
-
, (2008/06/13)
The present patent application discloses compounds of the formula STR1 wherein R 1 is C 1-10 saturated or unsaturated alkyl; or STR2 wherein R'" is H or STR3 R 2 is phenyl which is unsubstituted or substituted one or more times with halogen, CF 3, C. sub.1-6-alkoxy, NO 2, CO 2--C 1-6-alkyl, methyl; benzyl which may be substituted one or more times with halogen, CF 3, C 1-6-alkoxy, NO 2, CO 2--C 1-6-alkyl, methyl; pyridyl; or cyclohexyl;R 3 phenyl which is unsubstituted or substituted one or more times with halogen, CF 3, C 1-6-alkoxy, NO 2, CO 2--C 1-6-alkyl, methyl; naphthyl which may be substituted one or more times with halogen, CF 3, C 1-6-alkoxy, NO 2, CO 2--C 1-6-alkyl, methyl; pyridyl; C 1-6 unsaturated alkyl; furanyl;R 4 is H, C 1-6-alkyl, or benzyl; or STR4 together form STR5 R' and R" are each hydrogen or together form an extra benzo ring; and wherein the dotted line represents an optional extra bond between the two carbon atoms designated α and β, or a pharmaceutically-acceptable addition salt thereof.The compounds are useful as pharmaceuticals, for example in the treatment of Ca overload in brain cells. "
Imidazole derivatives as calcium channel blockers
-
, (2008/06/13)
The present patent application discloses compounds of the formula ψψ ψwhereinψ R1 is C1-10-alkyl which may be branched; C1-10-unsaturated alkyl; or CHR'''''' ψψ ψwherein R'''''' is H or ψψ ψRy is phenyl which may be substituted one or more times with halogen, CF3, C1-6-alkoxy, NO2, CO2-C1-6-alkyl, methyl; benzyl which may be substituted one or more times with halogen, CF3, C1-6-alkoxy, NO2, CO2-C1-6-alkyl, methyl; pyridyl; or cyclohexyl;ψ R3 phenyl which may be substituted one or more times with halogen, CF3, C1-6-alkoxy, NO2, CO2-C1-6-alkyl, methyl; naphthyl which may be substituted one or more times with halogen, CF3, C1-6-alkoxy, NO2, CO2-C1-6-alkyl, methyl; pyridyl; C1-6 unsaturated alkyl; furanyl;ψ R4 is H, C1-6-alkyl, or benzyl;ψ or ψψ ψtogether form ψψ ψR5 is H, or C1-6-alkyl;ψ R'' and R'''' are each hydrogen or together form an extra benzo ring;ψ and wherein the dotted line represents an optional extra bond between the two carbon atoms designated à and á, or a pharmaceutically-acceptable addition salt thereof. ψThe compounds are useful as pharmaceuticals, for example in the treatment of Ca overload in brain cells.ψ
Some Benzyl-Substituted Imidazoles, Triazoles, Tetrazoles, Pyridinethiones, and Structural Relatives as Multisubstrate Inhibitors of Dopamine β-Hydroxylase. 4. Structure-Activity Relationships at the Copper Binding Site
Kruse, Lawrence I.,Kaiser, Carl,DeWolf, Walter E.,Finkelstein, Joseph A.,Frazee, James S.,et al.
, p. 781 - 789 (2007/10/02)
Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine β-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor.Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously.The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity.An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitor potency.In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced.Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.
Synthesis of 2,4(5)-Bis(hydroxymethyl)imidazoles and 2,4(5)-Bisimidazoles: Precursors of 2,4(5)-Connected Imidazole Crown Ethers
Zimmerman, Steven C.,Cramer, Katherine D.,Galan, Adam A.
, p. 1256 - 1264 (2007/10/02)
Two syntheses of 1--2,4-bisimidazole, 3, a precursor to imidazole-containing crown ethers, are described.The first involved hydroxymethylation of 1-benzylimidazole with formaldehyde to afford 1-benzyl-2,5-bis(hydroxymethyl)imidazole (5) (20percent yield), which was elaborated into 3 in four steps.An alternative and more efficient route involved coupling of diamine 17b with the imino ether obtained from nitrile 11b to afford imidazoline 18b.The imidazoline was found to oxidize under Swern conditions, providing a mild new method of imidazole synthesis.Sulfamylation and debenzylation produced 3.This approach was also applied to the synthesis of 1--2,4-bis(hydroxymethyl)imidazole (2).Diol 3 was converted into 2,4-connected imidazole crown ethers, one of which (4) formed a crystalline complex with water.The complex structure was determined by X-ray crystallography.
Metalloenzyme Models. Divalent Metal Ion Catalyzed Hydrolysis of p-Nitrophenyl Picolinate in the Presence of Imidazoles and Pyridines Having Hydroxyl Groups in Their Side Chains
Ogino, Kenji,Shindo, Katsuhiko,Minami, Tooru,Tagaki, Waichiro,Eiki, Toshio
, p. 1101 - 1106 (2007/10/02)
Rate constants for hydrolysis of p-nitrophenyl picolinate at 25 deg C in the pH range 6.5-8.5 were measured in the absence and presence of divalent metal ions (Ni(II), Zn(II), Co(II), Ca, Mg) and substituted imidazoles or pyridines as ligands having alcoholic hydroxyl groups in their side chains. In the presence of either metal ion or ligand, the rate is slow and the pseudo-first-order rate constant (kobsd) increases linearly in a first-order manner with respect to the concentration of metal ion or ligand until it gives the second-order rate constant, kM or kL, respectively. In the presence of both a metal ion (Ni(II) or Zn(II)) and a ligand, rate increase is remarkable for some ligands and the increase in kobsd values constructs saturation curves with respect to increase in either metal ion or ligand concentration. The saturation curves were analyzed based upon rate equations formulated by assuming the formation of 1:1 complex of metal ion and ligands as the catalyst, leading to evaluation of the association constant K for complexes and the second-order rate constant kc for the reaction of complex with substrate. Values of kobsd, kc, and K are dependent greatly upon the structure of ligands and pH. The ligands complexed with Zn(II) ion appear to be simple but highly active models of hydrolytic metalloenzymes.
