Primofiore Giampaolo, Da Settimo Federico, Taliani Sabrina, Marini Anna Maria, Simorini Francesca, Novellino Ettore, Greco Giovanni, Trincavelli Letizia, Martini Claudia
Dipartimento di Scienze Farmaceutiche, Università di Pisa, Pisa, Italy.
Arch Pharm (Weinheim). 2003 Sep;336(9):413-21. doi: 10.1002/ardp.200300788.
A series of 3-benzylamino-and 3-arylalkylaminocarbonyl [1, 2, 4]triazino [4, 3-a]benzimidazoles 1-12 were synthesized and biologically assayed as geometrically constrained analogues of N-benzylindolylglyoxylylamides II, which are high affinity ligands at the benzodiazepine receptor (BzR). The intermediate 3-ethoxycarbonyl [1, 2, 4]triazino [4, 3-a]benzimidazol-4(10H)-one 14 and its N(10)-methyl analogue 15 closely related to 3-alkoxycarbonyl-beta-carbolines I were also investigated. The title compounds exhibited a lower affinity compared with the corresponding indolylglyoxylylamide derivatives II. Attempts were made to rationalize these results taking into account the possible tautomeric equilibria involving these ligands.
合成了一系列3-苄基氨基和3-芳基烷基氨基羰基[1,2,4]三嗪并[4,3-a]苯并咪唑1-12，并作为N-苄基吲哚基乙醛酰胺II的几何受限类似物进行了生物测定，N-苄基吲哚基乙醛酰胺II是苯二氮䓬受体（BzR）的高亲和力配体。还研究了与3-烷氧基羰基-β-咔啉I密切相关的中间体3-乙氧基羰基[1,2,4]三嗪并[4,3-a]苯并咪唑-4(10H)-酮14及其N(10)-甲基类似物15。与相应的吲哚基乙醛酰胺衍生物II相比，标题化合物表现出较低的亲和力。考虑到涉及这些配体的可能互变异构平衡，尝试对这些结果进行合理解释。
