Disease relevance of cyclopentane

• Overall, these results suggested that the presence of a carbonyl group at position 9 of the cyclopentane ring may be required for inhibitory activity as prostaglandins of the A and E series inhibited human melanoma cell growth [1].
• Cyclopentenone prostaglandins, which contain an alpha, beta-unsaturated carbonyl group in the cyclopentane ring and possess antiviral activity against several RNA and DNA viruses, were shown to function as signal for HSP synthesis in a nonstressful situation in a variety of mammalian cells [2].
• Oral administration of cyclopentane neuraminidase inhibitors protects ferrets against influenza virus infection [3].
• This study examined the cardioprotective effects and pharmacology of the novel adenosine A1/A2 receptor agonist ([1S-[1a,2b,3b, 4a(S*)]]-4-[7-[[2-(3-chloro-2-thienyl)-1-methylpropyl]amino]-3H-imida zo[4,5-b] pyridyl-3-yl] cyclopentane carboxamide) (AMP 579), in a model of myocardial infarction [4].
• Composite hopanoid biosynthesis in Zymomonas mobilis: N-acetyl-D-glucosamine as precursor for the cyclopentane ring linked to bacteriohopanetetrol [5].

Psychiatry related information on cyclopentane

• Structure-activity relationships of analogues in which the ester function and cyclopentane moieties were modified have been investigated by evaluating their ability to prevent seizures in the rat maximal electroshock test [6].

High impact information on cyclopentane

• These results strongly support the concept that PGs are involved in the regulation of cell proliferation, and that PGs containing a reactive alpha, beta-unsaturated carbonyl group in the cyclopentane ring are potential antineoplastic agents [7].
• To clarify the base pairing and coding potential of this major DNA lesion with the aim to estimate its mutagenic effect, we prepared oligonucleotides containing a cyclopentane based analogue of the DNA lesion (cFaPydG) [8].
• Solvent-controlled diastereoselective synthesis of cyclopentane derivatives by a [3 + 2] cyclization reaction of alpha,beta-disubstituted (alkenyl)(methoxy)carbene complexes with methyl ketone lithium enolates [9].
• These lipids are quite different from the usual fatty acid lipids of eukaryotes and prokaryotes: each molecule consists of two C40 omega-omega' biphytanyl residues (with 0 to 4 cyclopentane groups per residue), ether linked at both ends to two (variably substituted) glycerol or nonitol groups [10].
• The alpha- and omega-chains of BMP are involved in H-bonding with protein residues, while the cyclopentane moiety is surrounded by water molecules and is not directly attached to either the protein or the bound NADPH, indicating that the cyclopentane moiety is movable in the active site [11].

Chemical compound and disease context of cyclopentane

• The cyclopentane influenza virus neuraminidase inhibitor RWJ-270201 was evaluated against influenza A/NWS/33 (H1N1), A/Shangdong/09/93 (H3N2), A/Victoria/3/75 (H3N2), and B/Hong Kong/05/72 virus infections in mice [12].
• These results indicate that substitution of ribose with a cyclopentane ring in nucleotides is not well tolerated by HIV-1 reverse transcriptase [13].

Biological context of cyclopentane

• The mutagenic activities exhibited by cyclopenta[c]phenanthrenes are compared with those shown by the related cyclopenta[a]phenanthrenes and then discussed with respect to the effect of the cyclopentane ring facing the bay region [14].
• The inability of the less polar (cyclopentane carboxylic acid) analogs to inhibit ovulation could be explained, at least partially, in terms of impaired absorption sc [15].
• This prevents the dense packing characteristic for the cyclopentane ring-containing GDGTs membrane lipids used by hyperthermophilic crenarchaeota to adjust their membrane fluidity to high temperatures [16].
• For n-pentane, cyclopentane and, to a lesser extent methoxyflurane, the stimulus often declined to such low values that the axon exhibited spontaneous action potentials which persisted until the anaesthetic was removed [17].
• They include representatives of the three classes of anaesthetics examined in previous studies on the sodium current (Haydon & Urban, 1983a, b, c), i.e. the non-polar molecules n-pentane, cyclopentane and CCl4, several n-alkanols and the inhalation anaesthetics chloroform, halothane, diethyl ether and methoxyflurane [18].

Anatomical context of cyclopentane

• The anti cyclopentane analog 29b, was a low-micromolar inhibitor of the PMA-induced superoxide burst in neutrophils, and its carboxylic ester was a high-nanomolar inhibitor of neutrophils [19].
• It has been demonstrated in the CA1 region of the hippocampus in vitro, and in the dentate gyrus and CA1 region in vivo, that application of the metabotropic glutamate receptor (mGluR) agonist, 1S, 3R-amino cyclopentane 2,3-dicarboxylic acid triggers a slow-onset potentiation of synaptic transmission in the hippocampus [20].
• GDNT membranes containing eight cyclopentane rings in the molecule are packed much tighter than those without rings [21].
• The lipids employed were the fractions GroR2Gro (R represents an acyl group with variable chain length typically consisting of 0-4 cyclopentane rings and 40 isoprenoid residues) and GroR2GroNon-Ol (Non-ol represents nonitol) extracted from Sulfolobus solfataricus by hydrolysis of the cytoplasmic membrane [22].
• Novel cyclopentane-based 3-phenyl-1-hydroxypropyl compounds were evaluated for inhibitory activity against the peripheral nerve sodium channel Na(V)1.7 and off-target activity against the cardiac potassium channel hERG [23].

Associations of cyclopentane with other chemical compounds

• On ring carbomers of cyclobutane, cyclopentane, and cyclodecane and cyclization reactions through bis(alkynyl-propargyl) coupling [24].
• ACPTs are ACPD analogues in which a third carboxylic group has been added at position 4 in the cyclopentane ring [25].
• [reaction: see text] An efficient oxidative radical cyclization approach for the synthesis of 2-alkenyl cyclopentane or cyclohexane carboxylates from omega-silylallyl ester enolates induced by recyclable SET oxidant ferrocenium hexafluorophosphate has been developed [26].
• The pharmacological profile of this influx is strongly correlated with the pharmacological profile of the activation of phosphoinositide hydrolysis, i.e. quisqualic acid >> 1S,3R-amino-1-dicarboxylate-1,3 cyclopentane approximately equal to glutamate [27].
• The reactions of 3a-c with triethylamine are found to lead, however, to the unexpected stereoselective synthesis of the trisubstituted cyclopentane derivatives 4a-c, as confirmed by IR and NMR spectroscopy [28].

Gene context of cyclopentane

• The synthesis and structure-activity relationship (SAR) studies of a series of cyclopentane carboxylic acid matrix metalloproteinase (MMP) inhibitors are described [29].
• Potent and specific MMP-2, -3, -9, -13 inhibitors were obtained by regio- and stereoselective substitutions at positions 2 and 5 on the cyclopentane ring [29].
• Syntheses and neuraminidase inhibitory activity of multisubstituted cyclopentane amide derivatives [30].
• A novel series of cyclopentane derivatives have been found to exhibit potent and selective inhibitory effects on influenza virus neuraminidase [31].
• In this initial report, an intermolecular chlorination delivers a cyclopentane that is epimeric at C17 relative to the palau'amines and epimeric at C11 relative to the axinellamines [32].

Analytical, diagnostic and therapeutic context of cyclopentane

• Combined gas chromatography/negative-ion chemical ionization mass spectrometry analysis revealed for all three compounds the incorporation of one oxygen atom which according to the electron impact fragmentation pattern had to be introduced either at the 9-methylene group or at the cyclopentane ring [33].
• Cyanohydrin glycosides of Passiflora: distribution pattern, a saturated cyclopentane derivative from P. guatemalensis, and formation of pseudocyanogenic alpha-hydroxyamides as isolation artefacts [34].

References