- Setup of 4-Prenylated Quinolines through Suzuki-Miyaura Coupling for the Synthesis of Aurachins A and B
-
A polyprenyl side chain could be introduced into the heterocyclic quinoline moiety through Suzuki-Miyaura coupling of the corresponding quinoline-N-oxide with a polyprenyl boronic acid. This tool could be utilized for the synthesis of the natural product
- Stief, Laura,Speicher, Andreas
-
supporting information
p. 158 - 164
(2021/10/12)
-
- Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups
-
Described herein is the development of practical routes to 8-aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under RhIII-catalyzed conditions: i) the use of pre-generated chlorocarbamates and ii) a two-step one-pot process that directly employs carbamates. Both approaches are highly convenient for the gram-scale synthesis of 8-aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.
- Gwon, Donghyeon,Hwang, Heejun,Kim, Hye Kyung,Marder, Seth R.,Chang, Sukbok
-
supporting information
p. 17200 - 17204
(2016/01/25)
-
- Desazadesmethyldesferrithiocin analogues as orally effective iron chelators
-
Further structure-activity studies of desferrithiocin analogues are carried out. (S)-Desazadesmethyldesferrithiocin, 2-(2-hydroxyphenyl)-Δ2- thiazoline-4(S)-carboxylic acid, serves as the principal framework in the current paper. Desazadesmethyldesferrithiocin can be structurally altered with facility, and data are already available on its iron-clearing properties and toxicity parameters. Four different kinds of structural modifications of this framework are undertaken: introduction of hydroxy, carboxy, or methoxy groups on the aromatic ring; alteration of the thiazoline ring; increasing the distance between the ligand donor atoms; and benz-fusion of the aromatic rings. The structural modifications described are shown to have a tremendous impact on both the iron clearance and toxicity profiles of the desazadesmethyldesferrithiocin molecule. All of the compounds are assessed in a bile-duct-cannulated rodent model to determine iron clearance efficiency. Ligands which demonstrate an efficiency of greater than 2% are carried forward to the iron-overloaded primate for iron-clearing measurements. Ligands with efficiencies greater than 3% in the primate are then evaluated in a formal toxicity study in rodents. On the basis of the results of the present work, 2-(2,4-dihydroxyphenyl)-Δ2-thiazoline-4(S)-carboxylic acid is a promising candidate for clinical evaluation.
- Bergeron, Raymond J.,Wiegand, Jan,Weimar, William R.,Vinson, J. R. Timothy,Bussenius, J?rg,Yao, Guo Wei,McManis, James S.
-
-
- KINETICS OF N-OXIDATION OF COMPOUNDS OF THE QUINOLINE SERIES AND ISOMERIC BENZOQUINOLINES BY PERBENZOIC ACID IN CHLOROFORM AND AQUEOUS DIOXANE
-
The kinetics of the N-oxidation with perbenzoic acid of 15 derivatives of quinoline and benzoquinoline in chloroform and 19 compounds in 50percent aqueous dioxane at 20, 25, 30, and 35 deg C were subjected to a comparative study.The rate constants, parameters of Arrhenius equation, and the activation energies for the N-oxidation of the indicated monoazines were determined.A scale of the reactivities of derivatives of the quinoline series and benzoquinolines was calculated within the framework of general perturbation theory.
- Lokhov, R. E.
-
-