73818-80-1Relevant academic research and scientific papers
Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells
Kumar, Sarvesh,Singh, Brajendra K.,Arya, Pragya,Malhotra, Shashwat,Thimmulappa, Rajesh,Prasad, Ashok K.,Van Der Eycken, Erik,Olsen, Carl E.,Depass, Anthony L.,Biswal, Shyam,Parmar, Virinder S.,Ghosh, Balaram
, p. 5498 - 5511 (2011/12/15)
In the present study, we report the design and synthesis of novel analogs of cinnamates, thiocinnamates and thionocinnamates and evaluated the potencies of these analogs to inhibit TNF-α induced ICAM-1 expression on human endothelial cells. By using whole cell-ELISA, our screening data demonstrated that ethyl 3′,4′,5′-trimethoxythionocinnamate (ETMTC) is the most potent inhibitor of TNF-α induced ICAM-1, VCAM-1 and E-selectin. As functional consequences, ETMTC abrogated TNF-α induced adhesion of neutrophils to the endothelial monolayer. Structure-activity relationship studies revealed the critical role of the chain-length of the alkyl group in the alcohol moiety, number of methoxy groups in the aromatic ring of the cinnamoyl moiety and the presence of the α, β- C-C double bond in the thiocinnamates and thionocinnamates.
Thionation of esters and lactones with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane
Curphey, Thomas J
, p. 371 - 373 (2007/10/03)
The combination of P4S10 and hexamethyldisiloxane converts esters and lactones to thionoesters and thionolactones in yields comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent.
Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane
Curphey, Thomas J.
, p. 6461 - 6473 (2007/10/03)
The combination of P4S10 and hexamethyldisiloxane efficiently converts esters, lactones, amides, lactams, and ketones to their corresponding thiono derivatives. In the presence of elemental sulfur, 3-oxoesters are converted to dithiolethiones by this reagent. Yields are comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent.
Thiono, Selenothiono, and Dithiocarboxylic Ester Complexes from Pentacarbonyl(thiobenzaldehyde)tungsten and ?-Donor Substituted Alkynes and Decomplexation of the Esters
Fischer, Helmut,Treier, Kornelia,Troll, Carsten
, p. 883 - 890 (2007/10/02)
Pentacarbonyltungsten-coordinated thiobenzaldehyde, > (1), reacts with 1-methylthio-1-propyne, 1-ethylseleno-1-propyne, and alkoxyethynes by insertion of the CC into the S=C bond to form in a highly regio- and stereoselective manner the α,β-unsaturated dithio, selenothiono, and thionocarboxylic ester complexes (E)(C=C)1-S=C(XR')C(R)=C(Ph)H>> (3) (R = Me: XR' = SMe (a), SeEt (b); R = H: XR' = OEt (c), O-t-Bu (d)).The analogous reaction of 1 with bis(alkylthio)ethynes affords mixtures of the (E) and (Z)(C=C) isomers of 1-S=C(SR)C(SR)=C(Ph)H>> (6) a), t-Bu (b)>.The Z isomers are the initially formed products.Formation of (Z)-6 is followed by Z -> E isomerization until an equilibrium is obtained.For R = t-Bu isomerization is significantly faster than for R = Me.The dithio and thiono ester ligands can be cleaved intact from the metal by treatment with Br as shown by the examples of 3a, 3c, and 6a.Complex 3c has been characterized by an X-ray structural analysis. - Keywords: Thioaldehyde complexes / Dithioester complexes / Selenothiono ester complexes
Nouvelle methode de synthese de thiazolopyridines
Couture, Axel,Grandclaudon, Pierre,Huguerre, Eric
, p. 1765 - 1770 (2007/10/02)
It has been established that the direct condensation between aromatic and aliphatic thioesters and the variously generated anion of aminochloropyridines represents the best method for the synthesis of thiazolopyridines.The transient thioamides, sometimes isolated, can be easily converted chemically or photochemically into the desired fused heterocycles.
