74327-29-0Relevant articles and documents
Efficient Quantitative Analysis of Carboxyalkylpyrrole Ethanolamine Phospholipids: Elevated Levels in Sickle Cell Disease Blood
Guo, Junhong,Wang, Hua,Hrinczenko, Borys,Salomon, Robert G.
, p. 1187 - 1197 (2016)
γ-Hydroxy-α,β-unsaturated aldehydes, generated by oxidative damage of polyunsaturated phospholipids, form pyrrole derivatives that incorporate the ethanolamine phospholipid (EP) amino group such as 2-pentylpyrrole (PP)-EP and 2-(ω-carboxyalkyl)pyrrole (CAP)-EP derivatives: 2-(ω-carboxyethyl)pyrrole (CEP)-EP, 2-(ω-carboxypropyl)pyrrole (CPP)-EP, and 2-(ω-carboxyheptyl)pyrrole (CHP)-EP. Because EPs occur in vivo in various forms, a complex mixture of pyrrole-modified EPs with different molecular weights is expected to be generated. To provide a sensitive index of oxidative stress, all of the differences in mass related to the glycerophospholipid moieties were removed by releasing a single CAP-ethanolamine (ETN) or PP-ETN from each mixture by treatment with phospholipase D. Accurate quantization was achieved using the corresponding ethanolamine-d4 pyrroles as internal standards. The product mixture obtained by phospholipolysis of total blood phospholipids from sickle cell disease (SCD) patients was analyzed by LC-MS/MS. The method was applied to measure CAP-EP and PP-EP levels in blood plasma from clinical monitoring of SCD patients. We found uniformly elevated blood levels of CEP-EP (63.9 ± 9.7 nM) similar to mean levels in blood from age-related macular degeneration (AMD) patients (56.3 ± 37.1 nM), and 2-fold lower levels (27.6 ± 3.6 nM, n = 5) were detected in plasma from SCD patients hospitalized to treat a sickle cell crisis, although mean levels remain higher than those (12.1 ± 10.5 nM) detected in blood from healthy controls. Plasma levels of CPP-EPs from SCD clinic patients were 4-fold higher than those of SCD patients hospitalized to treat a sickle cell crisis (45.1 ± 10.9 nM, n = 5 versus 10.9 ± 3.4 nM, n = 6; p 0.002). PP-EP concentration in plasma from SCD clinic patients is nearly 4.8-fold higher than its level in plasma samples from SCD patients hospitalized to treat a sickle cell crisis (7.06 ± 4.05 vs 1.48 ± 0.92 nM; p 0.05). Because CAP-EPs promote angiogenesis and platelet activation, the elevated levels present in SCD blood can contribute to the hypercoaguability and vaso-occlusive events that are critical pathophysiologic features of SCD.
SUBSTITUTED CYCLOALKENE DERIVATIVE
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Page/Page column 191, (2008/12/06)
[Object] To provide a substituted cycloalkene derivative having an action to supress intracellular signal transduction or cell activation induced by endotoxin and to suppress cell responses due to the intracellular signal transduction and cell activation such as an excess generation of inflammatory mediators such as TNF-α, pharmacologically acceptable salts therefor, a medicament containing them as an active ingredient, a preparation method therefor, and a medicament containing the aforementioned substituted cycloalkene derivative as an active ingredient which is superior in prophylaxis and/or treatment of diseases such as sepsis (septic shock, disseminated intravascular coagulation, multiple organ failure and the like), that are associated with intracellular signal transduction or cell activation induced by endotoxin and to cell responses to the intracellular signal transduction and cell activation. [Solution] A compound represented by the general formula (I): {wherein X and Y represent a group in which X and Y together with a carbon atom to which they are bound form ring A (the ring is 3- to 7-membered heterocyclyl ring or 3- to 7-membered cycloalkyl ring), each represents a hydrogen atom, or X and Y together represent a substituent of ring B. 1 and m, independently from each other, represent an integer of 0 to 3, and 1 + m is 1 to 3. R1 is an aliphatic hydrocarbon group and the like which may be substituted with a group selected from Substituent group β and Substituent group γ. n represents an integer of 0 to 3. R2 is a C1-C6 alkyl group and the like which may be substituted with a group selected from a hydrogen atom and Substituent group β. R3 is a phenyl group, 5- to 6-membered heteroaryl group and the like which may be substituted with a group selected from Substituent group ε. R5 is a C1-C6 alkyl group and the like which may be substituted with a group selected from a hydrogen atom and Substituent group β. Provided that in the case where R3 is a phenyl group which may be substituted with a group selected from Substituent group ε, X and Y represent a group in which X and Y together with a carbon atom to which they are bound form ring A, or X and Y together represent a substituent of ring B.
Structure-activity relationship of anti-malarial spongean peroxides having a 3-methoxy-1,2-dioxane structure
Kawanishi, Motoyuki,Kotoku, Naoyuki,Itagaki, Sawako,Horii, Toshihiro,Kobayashi, Motomasa
, p. 5297 - 5307 (2007/10/03)
In order to study the structure-activity relationship of anti-malarial spongean peroxides, several analogues concerning with the 6-methoxyacetyl moiety and the 3-pentyl residue in methyl 2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl) acetate were synthesized and evaluated for anti-malarial activity. In order to study the structure-activity relationship of anti-malarial spongean peroxides, several analogues concerning with the 6-methoxyacetyl moiety and the 3-pentyl residue in methyl 2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl)acetate were synthesized and evaluated for anti-malarial activity. The tert-butyl ester analogue 14 showed stability in mouse serum and a high selectivity index against the malaria parasite, Plasmodium falciparum, and the citronellyl analogue 31 exhibited the strongest in vitro anti-malarial activity among them, and the imidazole analogue 25 showed desirable in vivo anti-malarial activity against P. berghei infected mice.
New readily accessible peroxides with high anti-malarial potency
Murakami, Nobutoshi,Kawanishi, Motoyuki,Itagaki, Sawako,Horii, Toshihiro,Kobayashi, Motomasa
, p. 69 - 72 (2007/10/03)
In an explorative study for new anti-malarial substances using the methyl esters (1 and 2) of peroxyplakoric acids A3 and B3 as scaffolds, 6-carbomethoxymethyl-3-methoxy-3-pentyl-1,2-dioxane, which has been readily synthesized from 6
Synthesis and Occurrence of Oxoaldehydes in Used Frying Oils
Takeoka, Gary R.,Buttery, Ron G.,Perrino, Charles T.
, p. 22 - 26 (2007/10/02)
As part of our efforts to identify volatile decomposition products in used frying oils, a series of 4- and 5-oxoaldehydes were synthesized, purified, and characterized by gas chromatography, gas chromatography-mass spectrometry, gas-chromatography-Fourier transform infrared spectrometry, and nuclear magnetic resonance spectrometry.Oxoaldehydes have been proposed as possible precursors of alkylfurans, which have potential anticancer effects.In a model reaction 4-oxononanal was refluxed in hexane for 40 days and only trace amounts of 2-pentylfuran were produced, suggesting that it is not a major precursor of the furan.The volatile constituents of used frying oils obtained from commercial food processors were studied, and 4-oxohexanal, 4-oxooctanal, 4-oxononanal, and 4-oxodecanal were identified.Keywords: Oxoaldehydes; odor threshold; frying oil
Synthesis of 2-Alkyl-2-cyclopenten-1-ones. A Versatile Kinetic Alkylation-Ozonolysis Procedure for the Preparation of γ-Ketoaldehydes
Geraghty, Niall W. A.,Morris, Noreen M.
, p. 603 - 607 (2007/10/02)
A range of 2-alkyl-2-cyclopenten-1-ones including the prostaglandin precursor 2-(6-methoxycarbonylhexyl)-2-cyclopenten-1-one and the jasmonoid precursor 2--2-cyclopenten-1-one, have been prepared by a short synthetic route which begins with 6-methyl-5-hepten-2-one and generates the key 1,4-ketoaldehyde intermediates by a kinetic alkylation-ozonolysis procedure.
SIMPLE METHOD FOR THE PRODUCTION OF ALKYL TRANS-2-METHOXYCYCLOPROPYL KETONES
Kulinkovich, O. G.,Tishchenko, I. G.,Sorokin, V. L.
, p. 1514 - 1518 (2007/10/02)
Alkyl 3-Chloro-2-methoxypropyl ketones, obtained in three stages from the corresponding alkanoyl chlorides, are converted by the action of an aqueous solution of sodium hydroxide into alkyl trans-2-methoxycyclopropyl ketones.During hydrolysis in a weakly acidic medium the latter form the corresponding γ-keto aldehydes.
A New and Convenient Method of Synthesis of γ-Ketoaldehydes
Kulinkovich, O. G.,Tischenko, I. G.,Sorokin, V. L.
, p. 1058 - 1059 (2007/10/02)
A new synthesis of 4-oxoalkanals starting from acid chlorides and allyl chloride proceeding via alkyl 2,3-dichloropropyl ketones, alkyl 3-chloropropenyl ketones, alkyl 3-chloro-2-methoxypropyl ketones, and 1-alkanoyl-2-methoxycyclopropanes is described.
