42893-53-8Relevant 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
experimental part, 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.
Conjugate reduction and reductive aldol cyclization of α,β- unsaturated thioesters catalyzed by (BDP)CuH
Li, Ninglin,Ou, Jun,Miesch, Michel,Chiu, Pauline
supporting information; experimental part, p. 6143 - 6147 (2011/10/08)
A conjugate reduction of α,β-unsaturated thioesters catalyzed by copper hydride using PMHS as stoichiometric reductant has been developed. 1,2-Bis(diphenylphosphino)benzene (BDP) was the most effective ligand for this reduction. Saturated thioesters could be produced in excellent yields when the substituent on the thiol is not sterically-demanding. This protocol was applied to induce the reductive aldol cyclization of keto-enethioates, which could offer β-hydroxythioesters in moderate to good yields.
Synthesis of thioesters by simultaneous activation of carboxylic acids and alcohols using PPh3/NBS with benzyltriethylammonium tetrathiomolybdate as the sulfur transfer reagent
Gopinath, Purushothaman,Vidyarini, Ravindran Sasitha,Chandrasekaran, Srinivasan
experimental part, p. 6043 - 6047 (2010/03/25)
A new and simple route for the synthesis of thioesters starting from carboxylic acids and alcohols is reported by using tetrathiomolybdate as the key sulfur transfer reagent, Triphenylphosphane and N-bromosuccinimide were used for the activation of the ca
Catalytic enantioselective synthesis of vicinal dialkyl arrays
Van Zijl, Anthoni W.,Szymanski, Wiktor,Lopez, Ferrnando,Minnaard, Adriaan J.,Feringa, Ben L.
supporting information; experimental part, p. 6994 - 7002 (2009/05/09)
(Chemical Equation Presented) With a consecutive "asymmetric allylic alkylation (AAA)/cross-metathesis (CM)/conjugate addition (CA)" protocol it is possible to synthesize either stereoisomer of compounds containing a vicinal dialkyl array with excellent stereoselectivity. The versatility of this protocol in natural product synthesis is demonstrated in the preparation of the ant pheromones faranal and lasiol.
New α-Sulfinyl-thioesters, as Precursors to Thioacrylates
Wladislaw, B.,Marzorati, L.,Gruber, J.
, p. 2937 - 2944 (2007/10/02)
Several substituted α-sulfinyl thioacetates, prepared by α-alkylation and α-sulfur oxidation methods, gave by thermal decomposition thioacrylates.
