| 1186004-58-9

• 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
• CAS: 1186004-58-9
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: QJKLVEQTQSMXOE-UPSATNDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (20R)-pregna-5,7-diene-3β,17α,20-triol 以 甲醇 为溶剂， 反应 14.0h， 生成 (3S,9R,10S,13S,14S,17R)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-1,2,3,4,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-diol 、 、 (1R,3aS,7aS)-1-[(1R)-1-hydroxyethyl]-4-[(E)-2-[(5S)-5-hydroxy-2-methylcyclohexen-1-yl]ethenyl]-7a-methyl-3,3a,6,7-tetrahydro-2H-inden-1-ol 、 、 (1R,3aS,4E,7aS)-1-[(1R)-1-hydroxyethyl]-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydroinden-1-ol
  参考文献：
  名称：

  Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3β, 17α, 20-triol and their bioactivity in melanoma cells

  摘要：

  Pregna-5,7-dienes and their hydroxylated derivatives can be formed in vivo when there is a deficiency in 7-dehydrocholesterol (7-DHC) A-reductase function, e.g.. Smith-Lemli-Opitz syndrome (SLOS). Ultraviolet B (UVB) radiation induces photoconversion of 7-DHC to vitamin D-3, lumisterol(3) and tachysterol(3). Two. epimers (20R and 20S) of pregna-5,7-diene-3 beta,17 alpha,20-triol (4R and 4S, respectively) were synthesized and their UVB photo-conversion products identified as corresponding 9,10-secosteroids with vitamin D-like and tachysterol-like structures, and 5,7-dienes with inverted configuration at C-9 and C-10 (lumisterol-like). The number and character of the products and the dynamics of the process were dependent on the UVB dose. At high UVB doses, the formation of multiple oxidized derivatives of the primary products, and the formation of 5,7,9(11)-triene, were observed. The production of vitamin D-like, tachysterol-like and lumisterol-like derivatives was also observed in human skin treated with 4R and 4S, and subjected to UV irradiation, as shown by RP-HPLC. Newly synthesized compounds inhibited melanoma growth in dose dependent manner, and some of them showed equal or higher potency than 1,25(OH)(2)D-3. In summary, we have characterized for the first time the products of UV induced conversion of pregna-5,7-diene-3 beta,17 alpha,20-triols and documented that the newly synthesized compounds have antiproliferative properties against melanoma cells. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.10.017