52483-31-5Relevant academic research and scientific papers
Tailoring Reaction Selectivity by Modulating a Catalytic Diad on a Foldamer Scaffold
Andrews, Mary Katherine,Gellman, Samuel H.,Liu, Xinyu
supporting information, (2022/02/10)
Use of a tunable molecular scaffold to align a reactive diad for bifunctional catalysis can reveal relationships between functional group identity and reactivity that might otherwise be impossible to identify. Here we use an α/β-peptide helix to show that an aligned pair of primary amine groups is uniquely competent to catalyze crossed aldol condensations with an aryl aldehyde as the electrophile. Geometrically similar diads in which one amine group is secondary, or both are secondary, are good catalysts for other types of aldol condensations but not those involving an aryl aldehyde. Catalytic efficacy requires β-amino acid residues that are preorganized for helix formation via cyclic constraint. Conventional peptides (exclusively α-amino acid residues) that display the primary amine diad are poor catalysts, which highlights the critical role of the foldamer scaffold.
Synthesis and biological evaluation of bilobol and adipostatin A
Tanaka, Ayano,Arai, Yasuhiro,Kim, Su-Nam,Ham, Jungyeob,Usuki, Toyonobu
experimental part, p. 290 - 296 (2011/06/19)
Concise total synthesis of bilobol 5-pentadecenylresorcinol (1), isolated from Gingko biloba fruits, has been achieved in 10 steps with 51% overall yield from 3,5-dihydroxybenzoic acid (3). Adipostatin A (2), isolated from the fruits as well as from Streptomyces cyaneus 2299-SV1, has also been synthesized in two steps from methylated bilobol (10). The structure-activity relationship study of synthetic products was described by means of cytotoxic assay against human KB carcinoma cell lines.
Naturally occurring 5-lipoxygenase inhibitors. vii. 1 practical synthesis of ardisiaquinones d, e and f
Fukuyama, Yoshiyasu,Kiriyama, Yuuko,Kodama, Mitsuaki
, p. 1770 - 1775 (2007/10/03)
The convergent synthesis of ardisiaquinones D (1), E (3) and F (4), isolated as 5-lipoxygenase inhibitors from Ardisia sieboldii, has been achieved efficiently by a cross-coupling reaction via an acetylene between two benzene units bearing appropriate fun
5-Alkylresorcinols from Hakea trifurcata that cleave DNA
Lytollis, William,Scannell, Ralph T.,An, Haoyun,Murty,Reddy, K. Sambi,Barr, John R.,Hecht, Sidney M.
, p. 12683 - 12690 (2007/10/03)
A dichloromethane extract of Hakea trifurcata that mediated relaxation of ?X174 replicative form DNA at micromolar concentrations in the presence of Cu2+ was resolved into six active components by bioassay-guided fractionation. Five of the acti
Long Chain Phenols. Part 17. The Synthesis of 5-resorcinol, 'Cardol monoene,' and of 5-resorcinol Dimethyl Ether, 'Cardol diene' Dimethyl Ether
Baylis, Christopher J.,Odle, Stanley W.,Tyman, John H. P.
, p. 132 - 141 (2007/10/02)
Two unsaturated compounds in the 'cardol' series, an important component phenol from Anacardium Occidentale, have been synthesised. 3,5-Dimethoxybenzaldehyde interacted with OH-protected 6-chlorohexan-1-ol in the presence of lithium to give, after acidic treatment, 1-(3,5-dimethoxyphenyl)heptane-1,7-diol which was hydrogenolysed selectively to 7-(3,5-dimethoxyphenyl)heptan-1-ol.Conversion into the bromide and alkylation of lithio-oct-1-yne gave 5-(pentadec-8-ynyl)resorcinol dimethyl ether which was selectively converted into the 8-(Z)-alkene.Dmethylation with lithium iodide gave 5-resorcinol which was identical to 'cardol monoene'.Reaction of 7-(3,5-dimethoxyphenyl)heptyl bromide with lithium derivative of OH-protected propargyl alcohol, gave after acidic treatment 10-(3,5-dimethoxyphenyl)dec-2-yn-1-ol, the bromide of which with pent-1-ynylmagnesium bromide afforded 5-pentadec-8,11-diynylresorcinol dimethyl ether.Selective hydrogenation yielded 5-resorcinol dimethyl ether identical with the dimethyl ether of 'cardol diene.'
