102260-50-4Relevant academic research and scientific papers
Synthesis and leishmanicidal activity of cinnamic acid esters: Structure-activity relationship
Otero, Elver,Robledo, Sara M.,Diaz, Santiago,Carda, Miguel,Munoz, Diana,Panos, Julian,Velez, Ivan D.,Cardona, Wilson
, p. 1378 - 1386 (2014/03/21)
Several cinnamic acid esters were obtained via Fischer esterification of cinnamic acids derivatives with aliphatic alcohols. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes and cytotoxic activity was evaluated against mammalian U-937 cells. The compounds 11, 15-17, and 23, were active against Leishmania parasite and although toxic for mammalian cells, they still are potential candidates for antileishmanial drug development. A SAR analysis indicates that first, while smaller alkyl chains lead to higher selectivity indices (10, 11 vs. 12-17); second, the degree of oxygenation is essential for activity, primarily in positions 3 and 4 (17 vs. 18-20 and 22); and third, hydroxyl groups increase both activity and cytotoxicity (14 vs. 23). On the other hand, the presence of a double bond in the side chain is crucial for cytotoxicity and leishmanicidal activity (12 vs. 21). However, further studies are required to optimize the structure of the promising molecules and to validate the in vitro activity against Leishmania demonstrated here with in vivo studies.
Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates
Menezes, Jose C.J.M.D.S.,Kamat, Shrivallabh P.,Cavaleiro, Jose A.S.,Gaspar, Alexandra,Garrido, Jorge,Borges, Fernanda
experimental part, p. 773 - 777 (2011/03/19)
Long chain alkyl hydroxycinnamates (8-21) were synthesized from the corresponding half esters of malonic acid (5-7) and benzaldehyde derivatives by Knoevenagel condensation. The total antioxidant capacity of these hydroxycinnamyl esters was evaluated usin
Liquid-Crystalline Solvents as Mechanistic Probes. 20. Crystalline and Smectic B Solvent Control over the Selectivity of Photodimerization of n-Alkyl Cinnamates
Ramesh, Varadaray,Weiss, Richard G.
, p. 2535 - 2539 (2007/10/02)
The photodimerizations of n-octadecyl, n-hexadecyl, and n-tetradecyl esters of trans-cinnamic acid have been investigated in the crystalline, smectic B, and isotropic phases of n-butyl stearate.A strong preference for head-to-tail dimerization is found in the ordered solvent phases.Dipole-dipole-induced interactions between cinnamates and solvent-mediated solute alignments are the factors that combine to control the regioselectivity of photodimerization.The ability of cinnamate esters to be incorporated into the ordered solvent phases is extremely dependent upon the length of the n-alkyl solute chains.However, ease of incorporation has little influence upon regioselectivity.
