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PubMed2000

Synthesis and preliminary biological evaluation of novel N-substituted 1-amino-3-[1-methyl(phenyl)-1H-indazol-4-yloxy]-propan-2-ols interesting as potential antiarrhythmic, local anaesthetic and analgesic agents.

A series of indazoloxypropanolamines 7 and 8, pindolol isosteres, were synthesized to extend the structure activity relationship (SAR) which was observed in an earlier series of related derivatives. Compounds 7, characterized by methyl substitution on the N-1 indazole nucleus, generally exhibited significant antiarrhythmic, local anaesthetic and analgesic activities. The preliminary radioligand binding assay highlighted, in compounds 7, an interesting beta 1-affinity which can be well correlated to their antiarrhyhtmic activity. Analogues 8 characterized by a phenyl group on the N-1 indazole nucleus, were generally less active as antiarrhyhtmic agents but generally interesting as local anaesthetics. Due to the importance of the indazole moiety as a carrier of antiphlogistic activity, the two classes of derivatives 7 and 8 were evaluated for their NSAID behaviour. Once again, compounds 7 resulted having more interesting analgesic and antipyretic effects than analogues 8.

Analgesics, Non-Narcotic↗
PubMed2004

Magnitude and orientation dependence of intermolecular interaction of perfluoropropane dimer studied by high-level ab initio calculations: comparison with propane dimer.

Intermolecular interaction energies of 12 orientations of C(3)F(8) dimers were calculated with electron correlation correction by the second-order Møller-Plesset perturbation method. The antiparallel C(2h) dimer has the largest interaction energy (-1.45 kcal/mol). Electron correlation correction increases the attraction considerably. Electrostatic energy is not large. Dispersion is mainly responsible for the attraction. Orientation dependence of the interaction energy of the C(3)F(8) dimer is substantially smaller than that of the C(3)H(8) dimer. The calculated interaction energy of the C(3)F(8) dimer at the potential minimum is 78% of that of the C(3)H(8) dimer (-1.85 kcal/mol), whereas the interaction energies of the CF(4) and C(2)F(6) dimers are larger than those of the CH(4) and C(2)H(6) dimers. The intermolecular separation in the C(3)F(8) dimer at the potential minimum is substantially larger than that in the C(3)H(8) dimer. The larger intermolecular separation due to the steric repulsion between fluorine atoms is the cause of the smaller interaction energy of the C(3)F(8) dimer at the potential minimum. The calculated intermolecular interaction energy potentials of the C(3)F(8) dimers using an all atom model OPLS-AA (OPLS all atom model) force field and a united atom model force field were compared with the ab initio calculations. Although the two force fields well reproduces the experimental vapor and liquid properties of perfluoroalkenes, the comparison shows that the united atom model underestimates the potential depth and orientation dependence of the interaction energy. The potentials obtained by the OPLS-AA force field are close to those obtained by the ab initio calculations.

Journal Article↗
PubMedDate not supplied

Membrane binding and transport of N-aminoethyl-1,2-diamino ethane (dien) and N-aminopropyl-1,3-diamino propane (propen) by rat liver mitochondria and their effects on membrane permeability transition.

This investigation is aimed at defining the structural requirements for aliphatic polyamines to interact with mitochondrial binding sites, which are relevant for the regulation of the permeability transition and for mitochondrial polyamine uptake. The triamines N-aminoethyl-1,2-diaminoethane (dien) and N-aminopropyl-1,3-diaminopropane (propen), both symmetric polyamines, are accumulated to differing extents by an energy-dependent mechanism in liver mitochondria. Propen is also able completely to inhibit the permeability transition of mitochondria, induced by Ca2+ plus phosphate, with the same efficacy as the asymmetric ubiquitary triamine spermidine, whereas dien fails to exhibit this effect. The competitive inhibition of both triamines on spermidine transport demonstrates that they bind to the same site(s) of this polyamine and exploit its transport system. The binding of dien and propen to mitochondrial membrane was studied by applying a thermodynamic model of ligand-receptor interactions developed both for equilibrium and far-from-equilibrium binding processes. Results show the presence of two mono-coordinated binding sites, S1 and S2, for propen, and one monocoordinated binding site for dien, all exhibiting high capacity and low affinity. Comparisons of the binding parameters of these polyamines with those of other natural polyamines reveal that, besides flexibility and hydrophilicity, as previously suggested, protonation of the imino group and the symmetry of the molecules for S1, and the presence of an aminobutyl group for S2, also contribute to the polyamine interactions observed in the two sites.

Animals↗
PubMed2002

Evaluation of two inhibitors of invasion: LY311727 [3-(3-acetamide-1-benzyl-2-ethyl-indolyl-5-oxy)propane phosphonic acid] and AEBSF [4-(2-aminoethyl)-benzenesulphonyl fluoride] in acute murine toxoplasmosis.

We examined the effect of an inhibitor of secretory phospholipase A2 type II (LY311727) and of a specific inhibitor of serine proteases (AEBSF) in a murine model of acute toxoplasmosis. LY311727 did not afford any significant protection and produced earlier mortality compared with untreated mice at a dose of 100 mg/kg. In contrast, AEBSF demonstrated a significant increase in length of survival, and this effect was enhanced when AEBSF was administered with non-protective doses of pyrimethamine.

Animals↗
PubMed2001

Subchronic inhalation toxicity of the chlorinated propane 1,1,1,3,3,3-hexachloropropane (HCC-230fa).

Male and female rats were exposed by inhalation (whole body) to HCC-230fa (1,1,1,3,3,3-hexachloropropane) for 6 h/day, 5 days/week over a 15-week period. Concentrations of 0, 0.50, 2.5, and 25 ppm were studied. A total of eight groups/sex were exposed. Four groups of male and four groups of female rats were used to measure clinical signs and growth, clinical pathology, and tissue pathology. The remaining four groups of male rats were used for immunotoxicological and sperm assessment evaluations, and the remaining four groups of female rats were used for immunotoxicological evaluation. Following the exposure period, surviving male rats were kept for a 1- or 3-month recovery period. Male and female rats exposed to 25 ppm had lower mean body weights, mean body weight gains, and food consumption during the exposure period. Male and female rats exposed to 25 ppm and sacrificed immediately after the exposure period had minimally decreased total leukocyte and lymphocyte counts. These changes were considered to be marginally adverse. Pathologic examination revealed hepatocellular hypertrophy in 0-day recovery males and an increased incidence and/or severity in chronic progressive nephropathy in 0-day, 1-month recovery, and 3-month recovery males at 25 ppm. No other pathological changes, including the testis, epididymis, and other accessory sex organs, were noted in rats during the study. Evaluation of sperm parameters at the end of the exposure period showed statistically significant decreases in epididymal sperm number per cauda epididymis, percent motile sperm, and percent normal sperm morphology at 25 ppm. The biological significance of the slight changes observed in the sperm parameters in the absence of histopathological changes is unclear. After a 1-month recovery period, no biologically significant differences in sperm parameters were noted at 25 ppm compared with controls. Exposure to HCC-230fa did not significantly alter the primary humoral immune response to sheep red blood cell (SRBC). Under the conditions of this study, the no-observed-adverse-effect level (NOAEL) was considered to be 2.5 ppm.

Administration, Inhalation↗
PubMed2001

Diaquabis(propane-1,2-diamine-N,N')nickel(II) bis(p-toluenesulfonate).

The crystal structure of the title compound, [Ni(C(3)H(10)N(2))(2)(H(2)O)(2)](C(7)H(7)O(3)S)(2) or [Ni(H(2)O)(2)[NH(2)CH(2)CH(NH(2))CH(3)](2)](CH(3)C(6)H(4)SO(3))(2), exhibits a layered structure in which the complex cations and the p-toluenesulfonate anions form alternating layers. The central Ni(II) atom of the cation resides on a crystallographic inversion centre and has a slightly distorted octahedral coordination composed of the water ligands bonding through oxygen in a trans arrangement and the N,N'-bidentate propanediamine ligands. The p-toluenesulfonate anions are arranged with the sulfonate groups turned alternately towards opposite sides of the layers. The structure of the layers is stabilized by a network of hydrogen bonds between the sulfonate O atoms, water molecules and the propanediamine N atoms.

Journal Article↗
PubMed2002

Propane-1,2-diammonium tetrafluoroberyllate.

Cocrystallization of the inorganic [BeF(4)](2-) unit with the organic moiety [NH(3)CH(2)CH(NH(3))CH(3)](2+) results in the three-dimensional network of the title compound, (C(3)H(12)N(2))[BeF(4)] or C(3)H(12)N(2)(2+).BeF(4)(2-), created by hydrogen bonds between the protonated ammonium groups and the highly electronegative F atoms of the anion. The structure is described in terms of layers related to each other by crystallographic centres of symmetry.

Journal Article↗
PubMed2004

(E)-1-(2-hydroxyphenyl)propan-2-one O-methyloxime forms hydrogen-bonded chains of edge-fused R(4)(4)(16) and R(4)(4)(24) rings.

The title compound, C(10)H(13)NO(2), crystallizes with Z' = 2 in space group P-1. The molecules are linked by two O-H.N hydrogen bonds [H.O = 1.97 and 1.98 A, O.N = 2.810 (2) and 2.815 (2) A, and O-H.N = 175 and 174 degrees ] and by one C-H.O hydrogen bond [H.O = 2.50 A, C.O = 3.313 (2) A and C-H.O = 144 degrees ] into chains of edge-fused centrosymmetric rings in which R(4)(4)(16) and R(4)(4)(24) rings alternate.

Journal Article↗
PubMed2004

(R)-4-(4-fluorophenyl)-1-[2-hydroxy-2-(3-methyl-1-benzofuran-2-yl)ethyl]piperazinium chloride propan-1-ol solvate.

The title compound, C21H24FN2O2+.Cl-.C3H8O, is a potential drug designed as a hybrid compound with antihypertensive, antioxidant and beta-adrenolytic activity. The cation contains nearly planar benzofuran and fluorophenyl ring systems, as well as a piperazine ring adopting an almost perfect chair conformation. The benzofuran and piperazine moieties are connected by an ethyl chain, the moieties forming a dihedral angle of 163.12 (13) degrees. In the crystal structure, ions and propanol solvent molecules are linked via N-H...Cl and O-H...Cl bonds into linear (010) chains.

Antihypertensive Agents↗
PubMed2004

An unexpected chelate conformation in trans-[(R)-N,N'-bis(alpha-phenylsalicylidene)propane-1,2-diaminato(2-)]bis(1-methyl-1H-imidazole-kappaN3)cobalt(III) perchlorate.

The title compound, [Co(C29H24N2O2)(C4H6N2)2]ClO4, contains an optically active tetradentate Schiff base ligand in an equatorial plane and two 1-methylimidazole ligands at apical positions. The central N-C-C-N chelate ring of the Schiff base ligand has an envelope structure with a lambda conformation, which is different from the solution structure predicted from circular dichroism and 1H NMR spectra.

Journal Article↗