7048-41-1Relevant academic research and scientific papers
8-OXOADENINE COMPOUND
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Page/Page column 144-145, (2010/11/24)
An 8-oxoadenine compound useful as an immuno-modulator having specific activity against Th1/Th2, specifically a prophylactic and therapeutic agent for a topical application for allergic diseases, viral siseases and cancers, which is represented by the following formula (1): , wherein A is a group of a formula represented by the formula (2): , wherein R2 is a substituted or unsubstituted alkyl group and so on, R3 is hydrogen atom or an alkyl group, R is a halogen atom and so on, n is 0-2, X1 is oxygen atom, Z is straight or branched chain alkylene, and R1 is an alkyl group which is optionally substituted by hydroxy group, an alkoxy group, alkoxycarbonyl group and so on, or its pharmaceutically acceptable salt.
(-)-5-Methyl-8-hydroxy-(di-n-propylamino)tetralin: A new 5-HT(1A) receptor antagonist
Trillat, Anne-Cecile,Mathe-Allainmat, Monique,Bremont, Beatrice,Malagie, Isabelle,Jacquot, Christian,Gardier, Alain M.,Langlois, Michel
, p. 437 - 444 (2007/10/03)
(±)-5-Me-8-OH-DPAT 4 was synthesized by a new synthetic pathway recently described by us. The (+)- and (-)-enantiomers 4 were prepared from the primary amine 8 by crystallisation of the (+)- and (-)-mandelic acid salts. The enantiomers reacted with propyl iodide and were demethylated by 48% HBr to the (+) and (-)-4 compounds. These compounds had good affinity for 5-HT(1A) receptors (K(i) = 32.9 ± 0.8 and 45.6 ± 2 nM, respectively) but lacked enantioselectivity. In contrast to 8-OH-DPAT, but similar to WAY 100635 and (±)-WAY 100135, the addition of GTP-γS did not decrease the affinity of these compounds for 5-HT(1A) receptors, suggesting a partial agonist or antagonist profile. Adenylyl cyclase assays with rat hippocampal membranes showed that (-)-4 was totally inactive as an agonist over a wide concentration range in contrast to (+)-4 which was a partial agonist. (-)-4 (1 and 10 μM) shifted the concentration-effect curve for the inhibition by 8-OH-DPAT of forskolin-stimulated cyclic AMP production to the right (pA2 = 7.6), demonstrating a competitive interaction between the two drugs.
Synthesis of a novel 1,4-bridged calix[8]arene 'host' cavity
Tsantrizos, Youla S.,Chew, Warren,Colebrook, Lawrence D.,Sauriol, Francoise
, p. 5411 - 5414 (2007/10/03)
A conformationally stable, acridone-based linker (1) was synthesized and attached to p-tert-butylcalix[8]arene (2) to form the novel 1,4-bridged calix[8] arene derivative 3. The structural assignment of 3 was based on its MS and high-field NMR data and su
Design and Synthesis of New Naphthalenic Derivatives as Ligands for 2-Iodomelatonin Binding Sites
Langlois, Michel,Bremont, Beatrice,Shen, Shuren,Poncet, Annie,Andrieux, Jean,et al.
, p. 2050 - 2060 (2007/10/02)
New melatonin-like agents were designed from the frameworks of 2,5-dimethoxyphenethylamine, an important structural moiety for the 5-HT receptor, and (2-methoxynaphthyl)ethylamine.The compounds were synthesized by classical methods and evaluated in binding assays with chicken brain membranes using 2-(125I>iodomelatonin as the radioligand.Preliminary studies on the series of N-acyl-disubstituted phenethylamines showed the favorable role of the methoxy group in the ortho position of the side chain on the affinity for the receptor ( Ki = 8 +/- 0.2 nM ) for N-propionamide (3o).This effect was confirmed in a series of the naphthalene derivatives, a bioisosteric moiety of the indole ring, and several potent ligands for melatonin binding sites were prepared such as N-propionamide (4b) ( Ki = 0.67 +/- 0.05 nM ) and N-cyclopropylformamide (Ki = 0.05 +/- 0.004 nM ( (4k).Structure-activity relationships are discussed with regard to melatonin and bioisosteric naphthalenic compound 2.The Ki value for 4b was affected to a similar extent to that of melatonin by GTP-γ-S or Mn2+ in competition experiments, suggesting an agonist profile for this compound.
Photochemistry of Stilbenes. 8. Eliminative Photocyclization of o-Methoxystilbenes
Mallory, Frank B.,Rudolph, M. Jonathan,Oh, Soon M.
, p. 4619 - 4626 (2007/10/02)
The synthetic value of the eliminative photocyclization of o-methoxystilbenes to give phenanthrenes with loss of the element of methanol has been enhanced by the use of tert-butyl alcohol as the solvent and sulfuric acid as a catalyst. 2-Methoxy-5-X-stilbenes and 2-methoxy-3-X-stilbenes undergo this photoreaction to produce the corresponding 2-X-phenanthrenes and 4-X-phenanthrenes, respectively.This regioselective photochemical route to these particular types of substituted phenanthrenes represents an improvement synthetically over the well-known oxidative photocyclization method with meta-substituted stilbenes, from which approximately 1:1 mixtures of 2-substituted and 4-substituted phenanthrenes usually are obtained.An attempt to extend the scope of this eliminative photocyclization method to the synthesis of benzanthracene by the ultraviolet irradiation of 3-methoxy-2-styrylnaphthalene was not successful, but this synthetic objective was achieved in an alternative way by the eliminative photocyclization of 5,6,7,8-tetrahydro-3-methoxy-2-styrylnaphthalene followed by oxidation of the resulting 8,9,10,11-tetrahydrobenzanthracene with DDQ.
Azethoxyl Nitroxide Spin-Labeled Crown Ethers and Cryptands with the N-O. Group Positioned near the Cavity
Keana, John F. W.,Cuomo, John,Lex, Laszlo,Seyedrezai, Seyed E.
, p. 2647 - 2654 (2007/10/02)
We report the synthesis and complexation properties of several nitroxide spin-labeled crown ethers and cryptands in which the N-O. group, in certain conformations, is thrust toward the cavity of the molecule.While initial approaches involving the cyclization of various unsymmetrically substituted tetraethylene glycols (e.g, 10, 11, and 15) were not promising, success was achieved by the sequential addition of substituted phenyl groups to nitrone 28, leading to nitroxide crown ethers 37 and 38.Nitroxide cryptand 60 was prepared by diacylation of diaza-18-crown-6 51 with azethoxyl nitroxide diacid chloride 57 followed by reduction.The ESR spectrum aN values of these nitroxides were not sensitive to the presence of K+, Na+, or Li+ in MeOH, While diaza-18-crown-6, decamethylene cryptand 55, and nitroxide cryptand 60 formed 1:1 complexes with NaBPh4 in CDCl3, nitroxide crown ethers 37 and 38 and amide 54 did not.Adaption of the quantitative methodology of Cram et al. showed that 55 and 60 bind Na+ somewhat better than dicyclohexyl-18-crown-6.K+ is bound better than Na+ by 55 and 60, tough not as strongly as dicyclohexyl-18-crown-6.The binding of K+ and Na+ by 37 and 38 is minimal.
