37529-27-4Relevant academic research and scientific papers
Design and synthesis of boronic acid inhibitors of endothelial lipase
O'Connell, Daniel P.,Leblanc, Daniel F.,Cromley, Debra,Billheimer, Jeffrey,Rader, Daniel J.,Bachovchin, William W.
scheme or table, p. 1397 - 1401 (2012/03/26)
Endothelial lipase (EL) and lipoprotein lipase (LPL) are homologous lipases that act on plasma lipoproteins. EL is predominantly a phospholipase and appears to be a key regulator of plasma HDL-C. LPL is mainly a triglyceride lipase regulating (V)LDL levels. The existing biological data indicate that inhibitors selective for EL over LPL should have anti-atherogenic activity, mainly through increasing plasma HDL-C levels. We report here the synthesis of alkyl, aryl, or acyl-substituted phenylboronic acids that inhibit EL. Many of the inhibitors evaluated proved to be nearly equally potent against both EL and LPL, but several exhibited moderate to good selectivity for EL.
Liquid-crystalline polymorphism of symmetrical azobananas: Bis(4-(4-alkylphenyl)azophenyl) 2-nitroisophtalates
Zygadlo,Dardas,Nowicka,Hofmann,Galewski
scheme or table, p. 283 - 291 (2011/08/02)
In this paper we present a series of novel compounds, bis(4-(4-alkylphenyl) azophenyl) 2-nitroisophtalates, which exhibit nematic and banana-type liquidcrystalline phases. The alkyl chain length varies from 1 to 18 carbons. The first ten members of this series exhibit nematic phase. The last eleven compounds exhibit banana-type liquid crystalline phases. The propyl and pentyl derivatives have extra second type of banana mesophase. Copyright Taylor & Francis Group, LLC.
Synthesis of Thiamacrocycles and Conformational Studies on Their Precursors
Abramovitch, Rudolph A.,Ye, Xiaocong,Pennington, William T.,Schimek, George,Bogdal, Dariuz
, p. 343 - 351 (2007/10/03)
1-(4-Nitrophenyl)-7-phenylthioheptane (1) and -9-phenylthiononane (2) have been synthesized and their conformations studied in solution and in the solid state. MMX calculations suggest that the global energy minimum structures are bent in the gas phase, probably owing to edge-to-face intramolecular attractive interaction between the electron rich and the electron poor terminal aryl groups. These conformations were confirmed in solution using 2D NOESY NMR. In the solid state, 1 and 2 exist in the staggered, linear conformation, stacked head-to-tail, with the plane of the nitro group being tilted above the plane of the benzene ring. It appears that the crystal lattice forces overcome the weak edge-to-face intramolecular aromatic interactions that dominate in the gas phase and in solution. The corresponding azides were treated with trifluoromethanesulfonic acid to generate the nitrenium ions, which underwent intramolecular ring-closure to give the corresponding 17- and 19-membered ring thiamacrocycles in modest yields. These results support the suggestion that MMX calculations on appropriate model compounds may be useful in predicting which precursors will lead to macrocycles and which will not.
Structure-activity relationships for the antileishmanial and antitrypanosomal activities of 1'-substituted 9-anilinoacridines
Gamage, Swarna A.,Figgitt, David P.,Wojcik, Stanley J.,Ralph, Raymond K.,Ransijn, Adriana,Mauel, Jacques,Yardley, Vanessa,Snowdon, Diane,Croft, Simon L.,Denny, William A.
, p. 2634 - 2642 (2007/10/03)
Members of the class of 9-anilinoacridine topoisomerase II inhibitors bearing lipophilic electron-donating 1'-aniline substituents are active against both the promastigote and amastigote forms of the parasite Leishmania major. A series of analogues of the known 1'-NHhexyl lead compound were prepared and evaluated against L. major in macrophage culture to further develop structure-activity relationships (SAR). Toxicity toward mammalian cells was measured in a human leukemia cell line, and the ratio of the two IC50 values (IC50(J)/IC50(L)) was used as a measure of the in vitro therapeutic index (IVTI). A 3,6-diNMe2 substitution pattern on the acridine greatly increased toxicity to L. major without altering mammalian toxicity, increasing IVTIs over that of the lead compound. The 2-OMe, 6-C1 acridine substitution pattern used in the antimalarial drug mepacrine also resulted in potent antileishmanial activity and high IVTIs. Earlier suggestions of the utility of 2'-OR groups in lowering mammalian cytotoxicity were not borne out in this wider study. A series of very lipophilic 1'-NRR (symmetric dialkylamino)-substituted analogues showed relatively high antileishmanial potency, but no clear trend was apparent across the series and none were superior to the 1'-NH(CH2)5Me subclass. Subsets of the most active 1'- N(R)(CH2)5Me- and 1'-N(alkyl)2-substituted compounds against L. major were also evaluated against Leishmania donovani, Trypanosoma cruzi, and Trypanosoma brucei, but no consistent SAR could be discerned in these physiologically diverse test systems. The present study has confirmed earlier conclusions that lipophilic electron-donating groups at the 1'-position of 9- anilinoacridines provide high activity against L. major, but the SAR patterns observed do not carry over to the other parasites studied.
Rates and Regioselectivities of the Palladium-Catalyzed Ethynylation of Substituted Bromo- and Dibromobenzenes
Singh, Rina,Just, George
, p. 4453 - 4457 (2007/10/02)
The Pd(0)/Cu2Br2-catalyzed ethynylation of 1,2-dibromo-4-nitro- and 1,2-dibromo-3-nitrobenzenes provide rapidly the product in which the bromine para or ortho to the nitro group is displaced, whereas the corresponding dibromoacetamidobenzenes provide the product of meta displacement slowly.Investigation of the rates of a series of para-substituted bromobenzenes indicates that the reaction is zero-order with respect to the heptyne and bromobenzene concentration, with a Hammett ρ value of 2.8.
LIQUID CRYSTALLINE PROPERTIES OF 4-CHLOROBENZYLIDENE-4-AKYLANILINES
Galewski, Zbigniew
, p. 233 - 242 (2007/10/02)
A new group of Schiff bases containing a polar terminal group was synthesized: .The alkyl was changed from n=1 to n=12.Based on calorimetric (DSC) studies and on observations of textures the phase situation was characterized.
Reaction of Azomethine Moiety Buried in Bilayer Membranes
Okahata, Yoshio,Ando, Reiko,Kunitake, Toyoki
, p. 802 - 808 (2007/10/02)
The reaction with water and amines of the azomethine moiety that is part of single-chain ammonium amphiphiles was examined.These amphiphiles form stable bilayer aggregates when they have the alkyl tail of C7 or C12.The reaction with water of the bilayer-forming amphiphiles ceases at the hydration stage and are 10-2000 times slower than those of the amphiphiles which do not form bilayers and undergo hydrolytic cleavage.The reactivity of the azomethine moiety in bilayers decreases with increasing distance from the membrane surface.The Arrhenius plots for the bilayer-forming amphiphiles show discontinuities at temperatures corresponding to phase transition of the respective bilayer (Tc).The apparent activation energy is larger at temperatures below Tc than at temperatures above Tc.This suggests that water penetration is facilitated in the fluid bilayer.The reaction with amines was affected by their solubility in the bilayer matrix, and poly(ethylenimine) gave a much reduced reaction rate when the azomethine moiety was buried deep in the bilayer matrix.
METAL COMPLEXES IN ORGANIC SYNTHESIS. VIII. ALLYLIC ALCOHOLS AS STARTING MATERIALS IN PALLADIUM-CATALYZED WITTIG-TYPE OLEFINIZATIONS.
Moreno-Manas,Truis
, p. 2154 - 2158 (2007/10/02)
Allylic alcohols, aldehydes, and triphenylphosphine participate in a one-pot process catalyzed by palladium, which is formally equivalent to the Wittig olefinization. It can be applied to both aliphatic and aromatic aldehydes. The resulting olefins which appear as mixtures of stereoisomers were fully hydrogenated. Two different mechanisms can account for the observed results.
DOUBLE BOND FORMATION BY ONE POT PALLADIUM INDUCED REACTIONS BETWEEN ALDEHYDES, ALLYLIC ALCOHOLS AND TRIPHENYLPHOSPHINE
Moreno-Manas, M.,Trius, A
, p. 3109 - 3112 (2007/10/02)
The reaction between several aldehydes, two allylic alcohols and triphenylphosphine under palladium catalysis leads to double bond formation, synthetically parallelizing the Wittig reaction.
