Derivatives of (Phenylsulfanyl)benzoic Acids with Multiple Antileukotrienic Activity

2004 ◽  
Vol 69 (11) ◽  
pp. 2098-2120 ◽  
Author(s):  
Miroslav Kuchař ◽  
Vojtěch Kmoníček ◽  
Vladimíra Panajotová ◽  
Antonín Jandera ◽  
Bohumila Brunová ◽  
...  

A series of derivatives of (phenylsulfanyl)benzoic acids bearing quinoline, 2,4-dihydroxy-3-propylacetophenone and 2,4-difluorobiphenyl moieties were prepared and their antileukotrienic activities evaluated. Some of the compounds were found to display multiple antileukotrienic effect in the inhibition of LTB4biosynthesis, binding to LTD4and LTB4receptors, superior to the standards (zileuton and zafirlukast) used. The compounds had an antiinflammatory effect, manifested with quinoline derivatives by a significant inhibition of bronchospasm induced by LTD4and/or albumin. The results of regression analysis correspond to the observation that the most active compounds belong to quinoline derivatives with the lowest lipophilicity. X-ray analysis of the quinoline compounds revealed that an intramolecular hydrophobic interaction of their aromatic rings does not occur in the solid state.

Molecules ◽  
2020 ◽  
Vol 25 (23) ◽  
pp. 5745
Author(s):  
Sergey A. Anufriev ◽  
Sergey V. Timofeev ◽  
Alexei A. Anisimov ◽  
Kyrill Yu. Suponitsky ◽  
Igor B. Sivaev

Complexation of the 8,8′-bis(methylsulfanyl) derivatives of cobalt and iron bis(dicarbollides) [8,8′-(MeS)2-3,3′-M(1,2-C2B9H10)2]− (M = Co, Fe) with copper, silver, palladium and rhodium leads to the formation of the corresponding chelate complexes, which is accompanied by a transition from the transoid to the cisoid conformation of the bis(dicarbollide) complex. This transition is reversible and can be used in design of coordination-driven molecular switches based on transition metal bis(dicarbollide) complexes. The solid-state structures of {(Ph3P)ClPd[8,8′- (MeS)2-3,3′-Co(1,2-C2B9H10)2-κ2-S,S′]} and {(COD)Rh[8,8′-(MeS)2-3,3′-Co(1,2-C2B9H10)2-κ2-S,S′]} were determined by single crystal X-ray diffraction.


2001 ◽  
Vol 79 (2) ◽  
pp. 195-200 ◽  
Author(s):  
Gerald W Buchanan ◽  
Majid F Rastegar ◽  
Glenn PA Yap

Benzo-9-crown-3 ether trimerizes in the presence of FeCl3 and aqueous H2SO4 to produce tris(9-crown-3)triphenylene in 25.4% yield. This compound crystallizes in the monoclinic P21/c space group: a = 13.759(2) Å, b = 13.318(2) Å, c = 13.399(2) Å, β = 96.883(2)°, with Z = 4. The three 9-crown-3 ether units of the trimer possess different geometries and there is substantial deviation from coplanarity in the three aromatic rings. 13C NMR chemical shifts in the solid state are consistent with this lack of symmetry and are discussed in terms of the X-ray crystal-structure data.Key words: crown ether, trimerization, stereochemistry.


1998 ◽  
Vol 51 (8) ◽  
pp. 707 ◽  
Author(s):  
Jack M. Harrowfield ◽  
Raj Pal Sharma ◽  
Todd M. Shand ◽  
Brian W. Skelton ◽  
Allan H. White

Room-temperature, single-crystal X-ray studies are recorded for the variously hydrated Group 1 metal derivatives of 2-nitrophenol (2-npH = C6H5NO3). A provisional determination is reported for Li(2-np).½H2O, set as monoclinic, P21/c, a 3·535(3), b 15·06(1), c 24·42(2) Å, β 91·7(1)°, Z = 8, conventional R on F currently 0·18 for No 875 ‘observed’ (I > 3σ(I)) reflections. Na(2-np).H2O is monoclinic, C2/c, a 34 ·23(2), b 3·624(4), c 35·48(2) Å, β 91·24(4)°, Z = 24, R 0·060 for No 1371. Rb(2-np).½ H2O is monoclinic, C2/c (isomorphous with the previously determined potassium analogue), a 25·269(9), b 5·381(5), c 12·010(3) Å, β 105·35(3)°, Z = 8, R 0·046 for No 1380. Cs(2-np).½H2O is monoclinic, P21/n, a 7·648(3), b 26·19(1), c 8·713(6) Å, β 111·75(2)°, Z = 8, R 0·061 for No 2347. All compounds except the lithium derivative are two-dimensional polymeric sheets in which the aromatic rings project to either side of a core of metal atoms coordinated by a web of 2-nitrophenoxide oxygen atoms in various bridging functionalities. The lithium compound is a novel ‘stair’ polymer with two crystallographically independent lithium atoms at successive independent Li–O crossbars, the oxygen atoms of which are phenoxide-Oof each of the two independent ligands. The lithium atoms are alternately four- and five-coordinate, the fourth coordination site of the first being occupied by the water molecule oxygen atom, while the fourth and fifth sites of the second are occupied by the cis-2-nitro oxygen atoms of the two ligands


2009 ◽  
Vol 344 (13) ◽  
pp. 1734-1744 ◽  
Author(s):  
Tomasz Gubica ◽  
Andrzej Temeriusz ◽  
Katarzyna Paradowska ◽  
Andrzej Ostrowski ◽  
Paulina Klimentowska ◽  
...  

1999 ◽  
Vol 576 ◽  
Author(s):  
Ronit Popovitz-Biro ◽  
Shouwu Guo ◽  
Volker Hensel ◽  
Edna Shavit ◽  
Meir Lahav

ABSTRACTThe preparation of lead sulfide and cadmium sulfide quantum size particles arranged in periodic layers within organic matrices is described. Superlattices of the particles have been generated in crystals or thin films of long chain amphiphilic acids by topotactic gas-solid reactions of the lead or cadmium salts, that pack in layer structures, with H2S gas. X-ray powder diffraction and transmission electron microscopy reveal that the crystalline order of the reactant has been partially retained in the organic-inorganic composite. This approach is demonstrated by examples of organic acids bearing an aromatic ring along the hydrocarbon chain, such as derivatives of phenyl propionic and benzoic acids.


1975 ◽  
Vol 28 (3) ◽  
pp. 525 ◽  
Author(s):  
JD Stevens

Two septanose derivatives of D-glucose, 1,2:3,4-di-O-isopropylidene-α-D-glucoseptanos(e4 a) and 2,3:4,5-di-O-isopropylidene-D-glucoseptanos(e5 a), have been isolated from the mixture of products formed by treating D-glucose with acidified acetone. Acid hydrolysis of (4a) yielded 1,2-O-isopropylidene- α-D-glucoseptanose which has been converted into a mixture of (4a) and a third D-glucoseptanose derivative, 1,2:4,5-di-O-isopropylidene-α-D-glucoseptanose (8a). Methylation of (5a) yielded the two D-glucoseptanoside derivatives, methyl 2,3:4,5-di-O-isopropylidene-α-D-glucoseptanoside and methyl 2,3:4,5-di-O-isopropylidene-β-D-glucoseptanosiwde, which have been selectively hydrolysed to give methyl α (and β-)-D-glucoseptanosides. Conformations of these various septanose compounds are proposed on the basis of n.m.r. parameters and these conformations are compared with those found in the solid state by X-ray analysis.


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