3β-acetoxy-5α-bromo-6β,19-epoxycholestan-24-one | 608538-49-4

• 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: 3β-acetoxy-5α-bromo-6β,19-epoxycholestan-24-one
• 英文别名: 5α-bromo-3β-acetoxyl-6,19-epoxy-cholest-24-one；[(1R,2S,5R,6R,9S,10S,12R,13R,15S)-13-bromo-5-methyl-6-[(2R)-6-methyl-5-oxoheptan-2-yl]-19-oxapentacyclo[10.5.2.01,13.02,10.05,9]nonadecan-15-yl] acetate
• CAS: 608538-49-4
• 化学式: C₂₉H₄₅BrO₄
• 分子量: 537.578
• InChiKey: YVGOIQGMXUWRSD-DZQMWMKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-5α-bromo-6β,19-epoxycholestan-24-one 在 甲酸 、 双氧水 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 17.25h， 生成 3β,5β,6α,19-tetrahydroxycholestan-24-one
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (IV): synthesis of 24-methylene-cholesta-3β,5α,6β,19-tetrol, a cytotoxic natural hydroxylated sterol

  摘要：

  The cytotoxic, polyhydroxylated sterol 24-methylene-cholesta-3beta,5alpha,6beta,19-tetrol (1), previously isolated from the soft corals Nephthea albida and N. tiexieral verseveldt, was synthesized using stigmasterol as the starting material by 10 steps in 9% overall yield. The spectral data and physical constants of 1 were identical with those of the natural product. This is the first report of the synthesis of 1. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.04.002
• 作为产物：
  描述：

  3β-acetoxy-cholest-5-en-24-one 在 高氯酸 、 碘 、 lead(IV) tetraacetate 、 calcium carbonate 作用下， 以 1,4-二氧六环 、 环己烷 、 水 、 苯 为溶剂， 反应 8.5h， 生成 3β-acetoxy-5α-bromo-6β,19-epoxycholestan-24-one
  参考文献：
  名称：

  Design and synthesis of polyhydroxy steroids as selective inhibitors against AKR1B10 and molecular docking

  摘要：

  AKR1B10 is a member of the human aldo-keto reductase superfamily which is highly expressed in several types of cancers, and has been regarded as a promising cancer therapeutic target. In this paper, a series of polyhydroxy steroids were designed and synthesized to selectively inhibit AKR1B10 activity. The most selective compound, novel compound 6, has an IC50 of 0.83 +/- 0.07 mu M and a selectivity of more than 120-fold for AKR1B10/AKR1B1. Structure-activity relation analyses indicate that hydroxyl at C-19 can significantly improve the selective inhibition of AKR1B10. The binding mode of AKR1B10 and its inhibitors were studied. (C) 2016 Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2016.03.004