郭婷, 吕亚琼, 叶丽萍, 王楠, 刘建平. 对称的吡嗪双甾体的简便合成方法[J]. 云南大学学报(自然科学版), 2016, 38(6): 940-946. doi: 10.7540/j.ynu.20160292
引用本文: 郭婷, 吕亚琼, 叶丽萍, 王楠, 刘建平. 对称的吡嗪双甾体的简便合成方法[J]. 云南大学学报(自然科学版), 2016, 38(6): 940-946. doi: 10.7540/j.ynu.20160292
GUO Ting, LYU Ya-qiong, YE Li-ping, WANG Nan, LIU Jian-ping. The simple synthesis of symmetric bis-steroidal pyrazines[J]. Journal of Yunnan University: Natural Sciences Edition, 2016, 38(6): 940-946. DOI: 10.7540/j.ynu.20160292
Citation: GUO Ting, LYU Ya-qiong, YE Li-ping, WANG Nan, LIU Jian-ping. The simple synthesis of symmetric bis-steroidal pyrazines[J]. Journal of Yunnan University: Natural Sciences Edition, 2016, 38(6): 940-946. DOI: 10.7540/j.ynu.20160292

对称的吡嗪双甾体的简便合成方法

The simple synthesis of symmetric bis-steroidal pyrazines

  • 摘要: 吡嗪双甾体是一类结构复杂的甾体-生物碱杂化体,它们不仅具有独特的化学结构,而且表现出极其显著的抗肿瘤活性.由于此类化合物的天然来源极其有限,所以吡嗪双甾体的应用有待于化学方法合成来实现.该文以甾体类化合物番麻皂甙元(hecogenin)、胆甾醇(cholesterol)、麦角甾醇(ergosterol)、豆甾醇(stigmasterol)等为原料,经羟基氧化及Rubottom氧化得到α-羟基酮甾体衍生物,将所得α-羟基酮与醋酸胺作用,一步合成得到对称的吡嗪双甾体类化合物.利用这种方法制备得到了10个对称的吡嗪双甾体类化合物,其中7个吡嗪双甾体未见报道(化合物7,14,25,26,28,29及35).与文献报道的方法相比,该研究工作简化了对称的吡嗪双甾体类似物的合成方法,为此类化合物的合成及进一步的活性研究打下了基础.

     

    Abstract: Pyrazino-bis-steroids are a group of complex steroid-alkaloid hybrids.These compounds not only possess the unique structural characteristics,but also show potent antitumor biological activities.They are difficult to obtain from the natural source and it has limited their bioactive studies.In this paper,a facile while flexible method towards the symmetric synthesis of the pyrazino-bis-steroids was developed using steroids such as hecogenin,choesterol,ergosterol,srigmaterol as basic materials.Pyrazino-bis-steroids were achieved in only one step by reacting of the key intermediate, 2-hydroxy-or 4-hydroxy-3-one steroid derivatives with ammonium acetate.Ten pyrazino-bis-steroids compounds were synthesized and seven of which were reported first time by our methodology.More symmetric pyrazino-bis-steroids should be easily synthesized for further studies easily with our methodology compared with the literature methods.

     

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