Design and synthesis of a novel intercalating isoxazolyl bis‐lexitropsin conjugate

Abstract

9‐Anthracene nitrile oxide directly generated from 9‐anthracenealdoxime and N‐chlorosuccinamide (NCS), reacts with dimethyl acetylenedicarboxylate (DMAD) and affords the corresponding 3‐(9′‐anthra‐cenyl)‐isoxazole‐4,5‐dicarboxylic acid ester (3) with good yield in a very short period. Double activation reaction between (3) and hydrogenated lexitropsin (5) in a 1:2 molar ratio, produced a bis‐lexitropsin product (6) (major product) and mono‐lexitropsin product (7).

Design, synthesis and biological evaluation of a novel class of anticancer agents: Anthracenylisoxazole lexitropsin conjugates

“…The dihedral angle between the tricyclic planar aromatic moiety and the isoxazole from our crystallographic studies of intermediates and analogs, is in the range of 74 – 80° 22, 26–8,44,45. The idealized helical pitch angle for B-DNA was estimated to be ca .…”

“…3-(9′-Anthracenyl) 5-methyl 4-isoxazolecaboxylate 17 , and the corresponding acridine 16 , 22 Anthracenyl ring analogs 18–20 26 27. and final product 33 28 were prepared according to methodology previously reported by our lab.…”

Five‐Membered Heterocycles: 1,2‐Azoles. Part 2. Isoxazoles and Isothiazoles

“…The reaction mechanism involves the nitration of Further examples of the use of 1,3-dipolar cycloaddition of nitrile oxides with alkenes and alkynes for the synthesis of isoxazoles have been published [144][145][146][147][148][149][150][151][152][153][154][155].…”

Preparation and crystal structures of two 3‐anthracenyl isoxazolyl sulfonamides

“…We previously reported a new class of isoxazoles [1][2][3], which were subsequently found to exhibit significant anticancer activity in the National Cancer Institute's 60 cell line screening protocol [4]. Our working hypothesis is based on the fact that the single-stranded G-rich overhang of the human telomere, or other similar oligonucleotide sequences, can adopt a G-quadruplex (G-4) structure, and stabilization of this G-4 by a small molecule ligand inhibits tumor cell proliferation.…”