Δ^14,15-14-dehydrobufalin | 7439-77-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: Δ^14,15-14-dehydrobufalin
• 英文别名: Δ^14,15-anhydrobufalin；Δ¹⁴-bufalin；3β-hydroxy-5β-bufa-14,20,22-trienolide；3β-Hydroxy-5β-bufa-14,20,22-trienolid；5-[(3S,5R,8R,9S,10S,13R,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
• CAS: 7439-77-2
• 化学式: C₂₄H₃₂O₃
• 分子量: 368.516
• InChiKey: LPARRDGBTTTYTR-RXXPFFJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Δ^14,15-14-dehydrobufalin 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以75 mg的产率得到3β-hydroxy-5β-bufa-8,14,20,22-tetraenolide
  参考文献：
  名称：

  Bufadienolides. 32. Selenium dioxide dehydrogenation of 14-dehydrobufalin

  摘要：

  DOI：

  10.1021/jo00347a026
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 Δ^14,15-14-dehydrobufalin
  参考文献：
  名称：

  Kuwada, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1939, vol. 60, p. 335,337

  摘要：

  DOI：

文献信息

• Bufospirostenin A and Bufogargarizin C, Steroids with Rearranged Skeletons from the Toad <i>Bufo bufo gargarizans</i>
  作者：Hai-Yan Tian、Li-Jun Ruan、Tong Yu、Qing-Fei Zheng、Nan-Hao Chen、Rui-Bo Wu、Xiao-Qi Zhang、Lei Wang、Ren-Wang Jiang、Wen-Cai Ye

  DOI：10.1021/acs.jnatprod.6b01018

  日期：2017.4.28

  Bufospirostenin A (1) and bufogargarizin C (2), two novel steroids with rearranged A/B rings, were isolated from the toad Bufo bufo gargarizans. Compound 1 represents the first spirostanol found in animals. Compound 2 is an unusual bufadienolide with a cycloheptatriene B ring. Their structures were elucidated by spectroscopic analysis, single crystal X-ray diffraction analysis, and computational calculations

  从蟾蜍蟾蜍蟾蜍中分离到两种具有重新排列的A / B环的新型类固醇Bufospirostenin A（1）和bufogargarizin C（2）。化合物1代表在动物中发现的第一种螺固醇。化合物2是具有环庚三烯B环的不寻常的丁二烯内酯。通过光谱分析，单晶X射线衍射分析和计算计算阐明了它们的结构。
• A bufadienolide derived androgen receptor antagonist with inhibitory activities against prostate cancer cells
  作者：Hai-Yan Tian、Xiao-Feng Yuan、Lu Jin、Juan Li、Cheng Luo、Wen-Cai Ye、Ren-Wang Jiang

  DOI：10.1016/j.cbi.2013.10.020

  日期：2014.1

  Molecular docking studies have shown that Delta(8,14)-anhydrobufalin (1) exhibited more potent binding affinity on androgen receptor (AR) than.Delta(14,15)-anhydrobufalin (2) and bufalin (3). To validate the docking results, compounds 1 and 2 were synthesized. The AR competitive binding assay indicated that the IC50 values of 1-3 were 1.9, >50 and >50 mu M (relative binding affinity), respectively, which confirmed that our theoretical binding mode was reliable and predictable. Furthermore, compound 1 was found to show more potent inhibitory activity against the androgen dependent LNCaP cancer cells than the androgen independent PO cancer cells, but exhibited less inhibition on the Na+/K+ ATPase as compared with the parent compound 3. To the best of our knowledge, compound 1 represented the first AR antagonist derived from bufadienolide discovered through a series of combined approaches of molecular docking and actual experimental validation. (C) 2013 Elsevier Ireland Ltd. All rights reserved.
• Kotake; Kuwada, Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1939, vol. 36, p. 106,108
  作者：Kotake、Kuwada

  DOI：——

  日期：——