(25R)-3α-azido-5α-spirostan-12-one | 1337908-46-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (25R)-3α-azido-5α-spirostan-12-one
• 英文别名: 3α-hecogenyl azide；(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16R,18S)-16-azido-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10-one
• CAS: 1337908-46-9
• 化学式: C₂₇H₄₁N₃O₃
• 分子量: 455.641
• InChiKey: IYFISJIOMZILIY-OZTLDDSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (25R)-3α-azido-5α-spirostan-12-one 在 水 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 74.0h， 生成
  参考文献：
  名称：

  Multicomponent Ligation of Steroids: Creating Diversity at the Linkage Moiety of Bis-spirostanic Conjugates by Ugi Reactions

  摘要：

  The diversity-oriented synthesis of novel bisspirostanic conjugates utilizing two different Up four-component reactions (Ugi-4CR) is described. Spirostanic steroids were functionalized with Ugi-reactive groups, that is, amines, isocyanides, and carboxylic acids, and next were subjected to multicomponent ligation approaches leading to bis-steroidal conjugates featuring pseudo-peptidic and hetero-cyclic linkage moieties. Both the classic Ugi-4CR and its hydrazoic acid variant were implemented, proving good efficiency for the ligation of isocyanosteroids to spirostanic acids and equatorial amines. Axially oriented amines showed poorer results, although model studies proved that chemical efficiency could be significantly improved while increasing reaction times. Overall, the method comprises the rapid generation of molecular diversity at the bis-steroid linkage moiety and, consequently, shows promise toward the production of combinatorial libraries of bis-spirostanes for biological screening.

  DOI：

  10.1021/co400028e
• 作为产物：
  描述：

  海柯吉宁 在 吡啶 、 sodium azide 作用下， 生成 (25R)-3α-azido-5α-spirostan-12-one
  参考文献：
  名称：

  Multicomponent Ligation of Steroids: Creating Diversity at the Linkage Moiety of Bis-spirostanic Conjugates by Ugi Reactions

  摘要：

  The diversity-oriented synthesis of novel bisspirostanic conjugates utilizing two different Up four-component reactions (Ugi-4CR) is described. Spirostanic steroids were functionalized with Ugi-reactive groups, that is, amines, isocyanides, and carboxylic acids, and next were subjected to multicomponent ligation approaches leading to bis-steroidal conjugates featuring pseudo-peptidic and hetero-cyclic linkage moieties. Both the classic Ugi-4CR and its hydrazoic acid variant were implemented, proving good efficiency for the ligation of isocyanosteroids to spirostanic acids and equatorial amines. Axially oriented amines showed poorer results, although model studies proved that chemical efficiency could be significantly improved while increasing reaction times. Overall, the method comprises the rapid generation of molecular diversity at the bis-steroid linkage moiety and, consequently, shows promise toward the production of combinatorial libraries of bis-spirostanes for biological screening.

  DOI：

  10.1021/co400028e

文献信息

• ‘Click’ synthesis of triazole-based spirostan saponin analogs
  作者：Karell Pérez-Labrada、Ignacio Brouard、Cercis Morera、Francisco Estévez、Jaime Bermejo、Daniel G. Rivera

  DOI：10.1016/j.tet.2011.08.003

  日期：2011.10

  great efficiency for the ligation of two bulky building blocks (e.g., chacotriose derivatives and spirostanes bearing axial azides), which enabled the rapid creation of a small library of triazole-based analogs for cytotoxicity evaluation. A molecular modeling study was performed to understand the conformational and electronic differences between a natural saponin and its triazole-based analogs.

  描述了螺环皂苷的新型类似物，其中糖苷键已被三唑键取代。为此，基于Cu I的直接寡糖-类固醇结合方法催化的叠氮化物-炔烃1,3-偶极环加成反应得以实现，从而导致皂苷类似物的各种组合具有三糖部分，人工连接和类固醇骨架功能化的变化。这种“点击”过程证明了用于连接两个笨重的构建基块（例如带有轴向叠氮化物的查三糖衍生物和螺环烷烃）的高效连接，从而能够快速创建一个小的三唑类类似物文库来进行细胞毒性评估。进行了分子建模研究，以了解天然皂苷及其基于三唑的类似物之间的构象和电子差异。