- Prospective new amidinothiazoles as leukotriene B4 inhibitors
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An efficient and one-step synthesis of the versatile, hitherto new derivatives resembling LY293111, a prospective potent antagonist of the leukotriene B4 (LTB4) receptor, were reported. The strategy was based on the synthesis of an amidinothiazole ring, c
- Aly, Ashraf A.,Ibrahim, Mahmoud A.A.,El-Sheref, Essmat M.,Hassan, Alaa M.A.,Brown, Alan B.
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p. 414 - 427
(2018/09/18)
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- 4-Phenoxybutoxy-substituted heterocycles - A structure-activity relationship study of blockers of the lymphocyte potassium channel Kv1.3
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The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC50 of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC50s of 150 nM to 10 μM in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC50 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers.
- Bodendiek, Silke B.,Mahieux, Cedrick,Haensel, Wolfram,Wulff, Heike
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experimental part
p. 1838 - 1852
(2009/09/08)
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- Structure-property correlations in model compounds of oligomer liquid crystals
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Structure-property correlations of the following model compounds for oligomer liquid crystals (LCs) have been investigated: monomers, C 6H5O(CH2)xCH3 (x = 4 and 5); dimers, C6H5O
- Sasanuma, Yuji,Ono, Tetsushi,Kuroda, Yoshihiko,Miyazaki, Emi,Hikino, Ken,Arou, Jun,Nakata, Kohji,Inaba, Hideaki,Tozaki, Ken-Ichi,Hayashi, Hideko,Yamaguchi, Kentaro
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p. 13163 - 13176
(2007/10/03)
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- Complexation of crown ethers and podands with tropylium cations: Determination of stability constants and crystal structure of the dibenzo-24-crown-8-tropylium cation complex
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The host-guest complexation of macrocyclic hosts and aromatic carbenium cations has been studied. Three different tropylium tetrafluoroborate compounds were prepared in order to study the interaction between positively charged guests and crown ether hosts
- Laemsae, Markku,Pursiainen, Jouni,Rissanen, Kari,Huuskonen, Juhani
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p. 563 - 570
(2007/10/03)
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- Dipole Moments and UV Spectra of some Long-chain Molecules
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About one hundred compounds with long-chain molecular structure have been prepared (most of them are new).The dipole moments of four α,ω-bis(p-methoxyphenylthio)alkanes and five α,ω-bis(p-methoxyphenylsulphonyl)alkanes have been determined to find the effect of chain-length.In the case of sulphones, the observed values are compared with the values calculated for free rotation around all bonds intervening the end dipoles.The uv spectra of some 1,2-(distyrylsulphonyl)ethanes, and a number of α,ω-bis(arylsulphonyl)- and α,ω-bis(aryloxy)alkanes have been recorded to examine the applicability of the principle of chromophore additivity.
- Baliah, V.,Aparajithan, K.
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p. 255 - 259
(2007/10/02)
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- Process for producing di(aryloxy)alkane
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A process for producing a high quality di(aryloxy)alkane with a high yield by the use of readily commercially available materials, without using any particular solvent or agent and by means of a simple operation and a general apparatus is provided, which process comprises subjecting a halogenated alkane of the formula (II) wherein X and Y each represent a halogen atom and A represents a lower alkylene group, and a phenol of the formula (III) STR1 wherein R1 to R5 each are same or different, represent hydrogen, halogen, lower alkyl, lower alkoxy, carboxylic acid salt, acyl or nitro group, and may form a ring in conjunction of two adjacent groups, to condensation reaction in the presence of an alkali in an aqueous medium to form a di(aryloxy)alkane of the formula (I) STR2 and is characterized (i) by carrying out the condensation reaction in a molar ratio of the compound of the formula (II): the phenol of the formula (III): the alkali in terms of monovalent base of 1:1.5 to 3.0:1.5 to 3.0; or (ii) by carrying out the condensation reaction of the above (i) and adjusting the quantity of the aqueous medium phase after completion of the reaction can be 35% or less based on the oily phase; or (iii) by carrying out the condensation reaction of the above (i), feeding at least the alkali among the reaction components with progress of the reaction and adjusting the quantity of the aqueous medium phase as described in the above (ii).
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- SYNTHETIC APPLICATION OF MICELLAR CATALYSIS. WILLIAMSON'S SYNTHESIS OF ETHERS
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A simple, rapid and efficient procedure for the preparation of di-alkyl, simple phenyl-alkyl and hindered phenyl-alkyl ethers has been developed.Based on the principle of micellar catalysis the method involves alkylation of the alkoxide or the phenoxide ion with an alkyl chloride at 80 deg C in the presence of cationic micelles.For the preparation of phenyl-alkyl ethers normal micelles were used, while for the di-alkyl ethers reverse micelles were more effective.By increasing the ionic strength of the solution the rate of formation of phenyl-alkyl ethers could be increased.
- Jursic, Branko
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p. 6677 - 6680
(2007/10/02)
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- Process for preparation of ethers
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A process for the preparation of ethers is described, comprising reacting an alcohol with an organic sulfonyl halide in a solvent in the presence of an alkali to form a sulfonate, and then reacting the sulfonate with a phenol, wherein the alkali is an ino
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- Ameliorations et simplification de la synthese des ethers phenoliques par alkylation d'ions phenates: catalyse par transfert de phase solide-liquide sans solvant
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Several aryl ethers can be obtained in excellent yields under mild and economical conditions in the absence of organic solvents by reacting stoechiometric amounts of corresponding phenol, finely ground KOH and alkyl bromides in the presence of 2percent Aliquat 336.This method is very favourable compared with recent works dealing with anionic activation.
- Loupy, Andre,Sansoulet, Jean,Zand, Farchid Vaziri-
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p. 1027 - 1035
(2007/10/02)
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