59770-98-8Relevant academic research and scientific papers
Synthesis of α-methylstilbenes using an aqueous Wittig methodology and application toward the development of potent human aromatase inhibitors
Nielsen, Alexander J.,Raez-Villanueva, Sergio,Crankshaw, Denis J.,Holloway, Alison C.,McNulty, James
supporting information, p. 1395 - 1398 (2019/04/03)
The development of aqueous Wittig methodology for the synthesis of α-methylstilbenes using tripropylphosphine-derived phosphonium salts is described. The Wittig olefination reaction was high yielding and allowed isolation of stilbenes by simple filtration and washing with water. The novel phosphonium salts employed were accessed via a highly efficient, regioselective addition of hydrogen bromide to styrenes. Application of the α-methylstilbenes toward the synthesis of a collection of stilbenoid-triazoles is reported and their inhibition of CYP450 19A1 (aromatase) investigated. The overall structure-activity profile provided additional evidence on the aryl halide-ketone bioisostere hypothesis and identified 6c as a potent inhibitor of aromatase in vitro (Ki = 8 nM).
Visible-light-mediated benzylic sp3 C-H bond functionalization to C-Br or C-N bond
Hou, Tianyuan,Lu, Ping,Li, Pixu
supporting information, p. 2273 - 2276 (2016/05/10)
A visible-light-promoted functionalization of unactivated benzylic sp3 C-H bonds was developed. Ethylbenzene derivatives were converted to the corresponding benzyl bromides or afforded benzylamine derivatives in a one-pot manner under visible light photoredox conditions.
MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF
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Paragraph 00330; 00331, (2013/08/28)
Agents for modulating methyl modifying enzymes, compositions and uses thereof are provided herein.
Triphenanthro-Anellated Annulenes with Alkoxy Side Chains - A Novel Class of Discotic Liquid Crystals
Kretzschmann, Holger,Mueller, Klaus,Kolshorn, Heinz,Schollmeyer, Dieter,Meier, Herbert
, p. 1735 - 1746 (2007/10/02)
Two different types 6 and 16 of annulenes condensed with phenanthrene systems were prepared by cyclocondensation reactions (Schemes 2 and 3).The central 18-membered rings do not show a macrocyclic diamagnetic ring current.Conformational analyses and X-ray analyses in the solid state reveal non-planar structures in which aromatic "islands" are connected by (E)-configurated olefinic bridges.The introduction of long alkoxy side chains yields a new class of discotic liquid crystals; either ND or hexagonal columnar phases are generated, which were characterized by DSC, microscopy with polarized light, and small-angle scanning X-ray. - Key Words: Annulenes / Liquid crystals, discotic
Studies in Nucleophilic Substitutions: Part I - Reactions between Phenylmethylcarbinols and Hydrobromic Acid and Structure-Reactivity Analysis
Ramakrishnan, S.,Venkatasubramanian, N.
, p. 60 - 62 (2007/10/02)
The kinetics of the reactions of phenylmethylcarbinol (PMC) and substituted PMCs with hydrobromic acid have been studied in 100percent acetic acid.The reaction rate follows total second order, first order each in and .The effect of substituents in the phenyl ring on the rate of substitution has been studied.The analysis of the rate data in terms of the Hammett equation gives a concave-down type of curve, though the Exner plot is linear.A stepwise mechanism involving the equilibrium formation of the conjugate acid of the alcohol followed by an attack by Br(-) accounts for the observed structure-reactivity pattern.
