Synthesis and Structure of Fluorescent Chelate Boron Complexes of 4-Anilinomethylidene-1-benzazepine-2,5-dione Ligands

Abstract

As analogues to the paullone kinase inhibitor family, boron chelate complexes of 4-anilinomethylidene-1-benzazepine-2,5-diones were prepared by reacting the ligands with boron trifluoride etherate or triphenylborane. The structures of the novel heterocyclic ring systems were established by X-ray structure analysis of two representative derivatives. The stability of the compounds in dimethylsulfoxide solution is dependent on the electronic properties of the aryl ring substituents. The fluorescent properties of the molecules are suitable for imaging the intracellular compound distribution by confocal laser microscopy.

Recent Advances in the Synthesis of Borinic Acid Derivatives

“…Because of this particular mechanism, most of the examples describe the use of triarylboranes bearing three identical aryl groups in order to prevent any mixture of different diarylborinates. As shown in Scheme 52 , a large variety of ligands on the organoborinates have been employed and can be sorted into three main categories: N,O -ligands [ 101 , 102 , 103 , 104 , 105 , 106 , 107 , 108 , 109 , 110 , 111 , 112 , 113 , 114 , 115 , 116 , 117 , 118 , 119 , 120 , 121 , 122 , 123 , 124 , 125 , 126 , 127 , 128 , 129 , 130 , 131 , 132 , 133 , 134 , 135 , 136 ], N , N -ligands [ 110 , 137 , 138 , 139 , 140 , 141 , 142 , 143 , 144 , 145 , 146 ...…”