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At least 19 recordsLinked to original sources
PubMed2006

Antidepressant-like profile of action of two 4-amine derivatives of 10,11-dihydro-5H-dibenzo [a,d] cycloheptane in mice evaluated in the forced swimming test.

This study investigated the antidepressant-like effect of 4-amine derivatives of 10,11-dihydro-5H-dibenzo-alkylamine-cycloheptane, 4-amine (3-N,N-dimethylpropylamine)-10,11-dihydro-5H-dibenzo[a,d]cycloheptane-5-one (ADDCH1) and 1,2,3,4,8,9-hexahydro-dibenzocyclohepta[4,4a,5-ef]1,4-diazepin (ADDCH2), in a validated experimental model of depression, the forced swimming test (FST) in mice. Female adult mice were sub-chronically (three doses in 24 h) or repeatedly (once a day for 10 days) treated with either of the compounds and evaluated in the FST. The sub-chronic treatment promoted a dose-dependent reduction in the immobility time in the FST with the doses of 50 mg/kg (ADDCH1) and 30 mg/kg (ADDCH2) ip being the most effective (33% and 37% of reduction, respectively). A similar profile of action was observed in the animals repeatedly treated with ADDCH1 50 mg/kg or ADDCH2 30 mg/kg ip (for 10 days) and there was no sign of motor impairment or locomotor activation as evaluated in the rota-rod and open-field tests, respectively. These findings suggest that these amine derivatives of the system dibenzocycloheptane have an antidepressant-like action which could be of clinical interest and, therefore, deserves further investigation. In addition, putative underlying mechanisms of action are discussed.

Amines↗
PubMed2006

New enantioselective entry to cycloheptane amino acid polyols.

[reaction: see text] A diversity-oriented protocol has been developed for the assembly of densely hydroxylated cycloheptane amino acids via succession of a vinylogous Mukaiyama aldol reaction (VMAR), a Morita-Baylis-Hillman reaction (MBHR), and an intramolecular pinacol coupling reaction (IPCR). The plan utilizes D- or L-configured glyceraldehyde derivatives as "chiral" surrogates of glyoxal and N-[(tert-butoxycarbonyl)-2-(tert-butyldimethylsilyl)oxy]pyrrole as the synthetic equivalent of the alpha,gamma-dianion of gamma-aminobutanoic acid. The parallel, asymmetric syntheses of four cycloheptane representatives proceed with high diastereocontrol and virtually complete enantioselectivity in ten steps and overall yields of 15-37%.

Aldehydes↗
PubMed2005

New synthesis of (Z,E)-2,7-bis(4-cyanobenzylidene)cycloheptan-1-one under stereospecific constraints induced by host-guest interactions.

A selective, efficient, and fast access to (Z,E)-2,7-bis(4-cyanobenzylidene)cycloheptan-1-one (BCBCH), precursor of the synthetic antagonist of tissue-plasminogen activator (t-PA), is reported using a solid/solid aldolisation-crotonisation reaction on a supramolecular complex under microwave irradiation. The underlying mechanism is investigated from the crystal structure of the intermediate host-guest complex formed between permethylated gamma-cyclodextrin and (Z)-2-(4-cyanobenzylidene)cycloheptan-1-one.

Cycloheptanes↗
PubMed2004

2,7-Bis-(4-amidinobenzylidene)-cycloheptan-1-one dihydrochloride, tPA stop, prevents tPA-enhanced excitotoxicity both in vitro and in vivo.

Tissue-type plasminogen activator (tPA) is available for the treatment of thromboembolic stroke in humans. However, adverse effects of tPA have been observed in animal models of ischemic brain injuries. In the present study, we have used a synthetic tPA inhibitor, named 2,7-bis-(4-amidino-benzylidene)-cycloheptan-1-one dihydrochloride (tPA stop), to investigate the role of endogenous tPA in the cerebral parenchyma. In mouse cortical cell cultures, we observed that although tPA stop reduced N-methyl-D-aspartic acid (NMDA)-mediated excitotoxic neuronal death, it failed to modulate alpha-amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazole propanoic acid or kainate-mediated necrosis. In addition, we found that tPA stop could prevent the deleterious effects of both endogenous and exogenous tPA during NMDA exposure. At the functional level, tPA stop was found to prevent tPA-dependent potentiation of NMDA receptor-evoked calcium influx. The relevance of those findings was strengthened by the observation of a massive reduction of NMDA-induced excitotoxic lesion in rats when tPA stop was co-injected. Altogether, these data demonstrate that the blockade of the endogenous proteolytic activity of tPA in the cerebral parenchyma could be a powerful neuroprotective strategy raised against brain pathologies associated with excitotoxicity.

Animals↗
PubMed2002

Alicyclobacillus herbarius sp. nov., a novel bacterium containing omega-cycloheptane fatty acids, isolated from herbal tea.

A thermo-acidophilic gram-positive bacterium, strain CP-1T, which grows aerobically at 35-65 degrees C (optimum 55-60 degrees C) and at pH 3.5-6.0 (optimum pH 4.5-5.0), was isolated from a herbal tea made from the dried flowers of hibiscus. Phylogenetic analysis of the 16S rRNA gene sequences showed that this bacterium was clearly distinguishable from previously described species of the genera Alicyclobacillus and Sulfobacillus. Strain CP-1T had unique omega-cycloheptane fatty acids as the major membrane lipid component, a characteristic which is peculiar to Alicyclobacillus cycloheptanicus. However, phenotypic and chemotaxonomic characteristics of strain CP-1T were different from those of the type strain of A. cycloheptanicus. DNA-DNA hybridization between the type strains of Alicyclobacillus species and Sulfobacillus disulfidooxidans was <20%, indicating that strain CP-1T represents a distinct species. On the basis of these results, the name Alicyclobacillus herbarius is proposed for this organism. The type strain is strain CP-1T (= DSM 13609T = IAM 14883T = NRIC 0477T).

Beverages↗
PubMed1981

Effects of a new antiarrhythmic compound [2-benzal-1-(2' diisopropyl-amino-ethoxy-imino)-cycloheptane hydrogen fumarate] on the electrophysiological properties of mammalian cardiac cells.

Intracellular microelectrodes were used to study the effects of Th 494 [2-benzal-1-(2' diisopropyl-amino-ethoxy-imino)-cycloheptane hydrogen fumarate; 1-100 mumol/1) on transmembrane electrical activity of sinus node and Purkinje fibres of the rabbit as well as on atrial trabeculae and papillary muscles of the guinea pig. In the atrial and in the ventricular myocardium (32 degrees C; driving rate 0.3-0.5 Hz) Th 494 exerted the following electrophysiological actions: no change of the resting potential nor of the amplitude of the action potential; concentration- dependent reduction of the maximum rate of rise (dV/dt)max of the action potential; slight increase of the action potential duration at lower concentrations (1-20 mumol/l), loss of the plateau at higher concentrations (above 20 mumol/l). The isometric force of contraction was moderately reduced by Th 494 (about 20% reduction by 2 mumol/l). The h infinity-curve relating (dV/dt)max of the action potential to the membrane potential was depressed by Th 494 without being shifted along the voltage axis. The reduction of (dV/dt)max was considerably more pronounced at higher driving frequencies. After interruption of stimulation for various periods, (dV/dt) max of the first action potential attained a steady-state value in a two-exponential fashion, suggesting use-dependence as well as a change in the recovery kinetics of the fast Na+ channel by Th 494. In Purkinje fibres (37 degrees C) Th 494 reduced (dV/dt) max in a similar manner. The duration of the action potential was considerably decreased at the level of the plateau. In the primary pacemaker region of the sinus node (37 degrees C) Th 494 moderately reduced the rate of diastolic depolarization and diminished at higher concentrations the amplitude of the action potential. All effects of Th 494 were only slowly reversible by drug-free perfusion. In view of its effect on (dV/dt) max, Th 494 resembles quinidine in its potential-dependence, whereas its time-dependence bears greater similarity with lidocaine.

Action Potentials↗
PubMed2005

Silylcuprates from allene and their reaction with alpha,beta-unsaturatedd nitriles and imines. Synthesis of silylated oxo compounds leading to cyclopentane and cycloheptane ring formation.

The silylcupration of allenes and the subsequent capture of the intermediate cuprate with alpha,beta-unsaturated nitriles is reported. The influence of the substitution of the nitrile, the nature of the silylcopper species, and the temperature on the selectivity of the reaction is studied. An interesting diaddition process was observed (1,2-addition and 1,4-addition), leading to oxo compounds which simultaneously have an allylsilane and a vinylsilane group. The different reactivity of these two units has been employed in the intramolecular allylsilane-terminated cyclization of these adducts, where the vinylsilane moiety remains unchanged. To shed some light on the reaction pathway, the behavior of alpha,beta-unsaturatedd imines was also checked and a new and convenient way for cycloheptane annulation presented. In light of the former results a feasible mechanism is proposed.

Journal Article↗
PubMed1996

Bridged to Fused Ring Interchange. Methodology for the Construction of Fused Cycloheptanes and Cyclooctanes. Total Syntheses of Ledol, Ledene, and Compressanolide.

The type two intramolecular Diels-Alder reaction (T2IMDA) is an efficient method for the formation of medium rings. The methodology is particularly effective for the construction of seven- and eight-membered rings. A strategy for the synthesis of functionalized cycloheptanes and cyclooctanes has been developed that involves a bridged to fused ring interchange. The T2IMDA provides a synthesis for rigid bridged bicyclic molecules that can be stereoselectively elaborated before ozonolysis of the bridgehead double bond. Following oxidative cleavage, aldol condensation provides fused bicyclic ring systems that otherwise are difficult to synthesize. This methodology is amenable to the synthesis of terpene natural products. This is demonstrated here through total syntheses of (+/-)-ledol and (+/-)-ledene and a formal synthesis of (+/-)-compressanolide.

Journal Article↗
PubMed2005

4,4'-Dimethyldinaphtho[a,d]cycloheptane, a naturally occurring polyaromatic derivative related to triterpenoids of the serratane series.

[reaction: see text] The polyaromatic hydrocarbon 4,4'-dimethyldinaphtho[a,d]cycloheptane (1a) has been identified by NMR studies after isolation from an Oligocene sediment. The original symmetrical structure of 1a, which bears a central seven-membered ring, is closely related to higher plant triterpenoid precursor(s) of the serratane series and is believed to have been formed in the subsurface by a microbially mediated aromatization process.

Molecular Structure↗
PubMed1984

[Animal experimental studies on the pharmacology of a new anti-arrhythmic of the imino-cycloheptane series, stirocainide].

The action of 2- benzal -1-(2'-diisopropyl-amino-ethoxy-imino)- cycloheptane hydrogenfumarate ( Stirocainide , Th 494) has been investigated on isolated guinea-pig atria and papillary muscles and on the circulation of the anaesthetized and conscious cat. Th 494 is characterized as a Na+-inhibitory antiarrhythmic agent in isolated atria and papillary muscles. 1-10 mumol/l Th 494 induces only a small increase in action potential duration in both preparations, whereas no change in resting potential or amplitude of the action potential is observed. The action on the maximal rate of rise of the action potential (Vmax) depends on the rate of stimulation ("use-dependence"), this effect being somewhat smaller in atria as compared to papillary muscles. The increase in threshold of alternating current induced arrhythmias and in functional refractory period is also smaller in atria. Isometric force of contraction is reduced by Th 494 in guinea-pig atria and papillary muscles to a greater extent than in rabbit and cat. In the anaesthetized cat 2 mg/kg Th 494 i.v. induces a transient decrease in heart rate and a decrease in the maximal rise of left ventricular pressure. In addition, 4 mg/kg i.v. induces a transient decrease in systolic and diastolic blood pressure as well as a broadening of the QRS complex in the ECG. High doses of 4 and 8 mg/kg, respectively, lead to arrhythmias and apnoea, 8 mg/kg to exitus. Atropine does not influence the action of Th 494. 2 and 4 mg/kg Th 494 do not alter the action of norepinephrine on heart and circulation.(ABSTRACT TRUNCATED AT 250 WORDS)

Action Potentials↗
PubMed1979

The metabolism of benzyclane [1-benzyl-1-(3-N,N-dimethylaminopropoxy)cycloheptane] in rat and man.

1. Two metabolites, isolated from the urine of rats dosed with bencyclane fumarate, were characterized as cis-1-benzyl-1-(3-N,N-dimethylaminopropoxy)-4-hydroxycycloheptane (metabolite I) and 1-benzyl-1-(3-N,N-dimethylaminopropoxy)-4-oxocycloheptane (metabolite II). 2. Bencyclane and the two metabolites were determined in the urine of rats and volunteers by g.l.c. Metabolite I was a major metabolite in men, being excreted in urine to the extent of 23.5% dose in the first 24 h.

Animals↗