PDF(Pubmed)
Abstract：
By reducing the 2-nitrophenylhydrazone of cyclohexanone with sodium dithionite, an unexpected yellow compound was obtained instead of the corresponding colorless amino derivative. Many years later, the structure of this compound, namely, cyclohexane-3-spiro-3,4-dihydro-1,2,4-benzotriazine, was demonstrated. From that time, the reduction of 2-nitrophenylhydrazones of different kinds of ketones, followed by air oxidation of the initially formed amino compounds, has represented a general way to synthesize a variety of 3,3-disubstituted 3,4-dihydro-1,2,4-benzotriazines. Many derivatives have been obtained so far by a single research group, and most of them have demonstrated interesting pharmacological activities, mainly antihypertensive, anti-inflammatory, and diuretic effects and other activities with lower diffusion. Moreover, 3,3-disubstituted 3,4-dihydro-1,2,4-benzotriazines represent a novel class of ligands for sigma receptors, with nanomolar affinity to the σ1 subtype. This property might promote the development of agents for cardiovascular, neurodegenerative, and proliferative pathologies. The present commentary, by collecting compounds and biological results obtained so far, intends to celebrate the centennial of the discovery of the first member of this class of compounds and to promote further investigation in the field.
摘要：
通过用连二亚硫酸钠还原环己酮的2-硝基苯腙，得到意想不到的黄色化合物代替相应的无色氨基衍生物。许多年后,这种化合物的结构，即,环己烷-3-螺-3,4-二氢-1,2,4-苯并三嗪，被证明了。从那时起,还原不同种类的酮的2-硝基苯基腙，然后是最初形成的氨基化合物的空气氧化，代表了合成多种3,3-二取代的3,4-二氢-1,2,4-苯并三嗪的一般方法。到目前为止，一个研究小组已经获得了许多衍生物，它们中的大多数已经表现出有趣的药理活性，主要是抗高血压药,抗炎,和利尿作用和其他活动与较低的扩散。此外，3,3-二取代的3,4-二氢-1,2,4-苯并三嗪代表了σ受体的一类新型配体，与σ1亚型具有纳摩尔亲和力。这种特性可能会促进心血管疾病药物的发展，神经退行性疾病，和增殖性病理。本评注,通过收集迄今为止获得的化合物和生物学结果，打算庆祝发现此类化合物的第一个成员一百周年，并促进该领域的进一步研究。
