84775-31-5Relevant academic research and scientific papers
Antileishmaniai chalcones: Statistical design, synthesis, and three- dimensional quantitative structure-activity relationship analysis
Nielsen, Simon Feldb?k,Christensen, S?ren Br?gger,Cruciani, Gabriele,Kharazmi, Arsalan,Liljefors, Tommy
, p. 4819 - 4832 (1998)
A large number of substituted chalcones have been synthesized and tested for antileishmanial and lymphocyte-suppressing activities. A subset of the chalcones was designed by using statistical methods. 3D-QSAR analyses using 67 (antileishmanial activity) and 63 (lymphocyte-suppressing activity) of the compounds for the training sets and 9 compounds as an external validation set were performed by using the GRID/GOLPE methodology. The Smart Region Definition procedure with subsequent region selection as implemented in GOLPE reduced the number of variables to approximately 1300 yielding 3D-QSAR models of high quality (lymphocyte-suppressing model, R2 = 0.90, Q2 = 0.80; antileishmanial model, R2 = 0.73, Q2 = 0.63). The coefficient plots indicate that steric interactions between the chalcones and the target are of major importance for the potencies of the compounds. A comparison of the coefficient plots for the antileishmanial effect and the lymphocyte- suppressing activity discloses significant differences which should make it possible to design chalcones having a high antileishmanial activity without suppressing the proliferation of lymphocytes.
A Facile General Route to Enantiomeric 1-(4-Hydroxyphenyl)alkanols, and an Improved Synthesis of 4-Vinylphenol
Everhart, E. Thomas,Craig, J. Cymerman
, p. 1701 - 1707 (2007/10/02)
Optically pure 1-(4-hydroxyphenyl)alkanols, the phenolic hydroxy groups of which are protected, have been obtained by an improved resolution procedure.Since subsequent deprotection of these is accompanied by complete elimination to the phenolic styrenes, an efficient synthesis of 4-vinylphenol from the racemic protected alcohols by simultaneous deprotection and elimination at 0 deg C has been developed. The target chiral 1-(4-hydroxyphenyl)alkanols have been prepared by treatment of the O-protected 4-hydroxyphenyl alkyl ketone with the enantiomers of chlorodiisopinocampheylborane at 0 deg C, when asymmetric reduction and simultaneous deprotection gives the enantiomeric diols in >99.7percent e.e. and high chemical yield.
