D-homo-5α-androstan-3-one | 39851-65-5

• 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: D-homo-5α-androstan-3-one
• 英文别名: D-homo-5α-androstanone-(3)；D-Homo-5α-androstanon-(3)；D-Homo-5α-androstan-3-on
• CAS: 39851-65-5
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: GTSAEIMAUOBPIC-ZXIXUEFNSA-N

物化性质

• 熔点：
  168.5-170 °C
• 沸点：
  382.9±10.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  D-homo-5α-androstan-3-one 在 sodium tetrahydroborate 作用下， 生成 (4aS)-4ar.6ac-dimethyl-(4btH.10atH.10bcH.12atH)-octadecahydro-chrysenol-(2t)
  参考文献：
  名称：

  D-homoandrostanes. I. Preparation and properties of D-homo-5.alpha.-androstan-1-,-2-,-3-, and -4-ones

  摘要：

  DOI：

  10.1021/jo00924a022
• 作为产物：
  描述：

  表雄酮 在 chromium(VI) oxide 、 硫酸 作用下， 生成 D-homo-5α-androstan-3-one
  参考文献：
  名称：

  D-homoandrostanes. I. Preparation and properties of D-homo-5.alpha.-androstan-1-,-2-,-3-, and -4-ones

  摘要：

  DOI：

  10.1021/jo00924a022

文献信息

• Mass spectrometry in structural and stereochemical problems. CCXI. Effect of structural variations on the electron impact-induced fragmentations of steroid hydrocarbons
  作者：George Eadon、S. Popov、Carl Djerassi

  DOI：10.1021/ja00759a040

  日期：1972.2
• D-Alpha-Tocopheryl Succinate (Vitamin E) Enhances Radiation-Induced Chromosomal Damage Levels in Human Cancer Cells, but Reduces it in Normal Cells
  作者：Bipin Kumar、Mitra N. Jha、William C. Cole、Joel S. Bedford、Kedar N. Prasad

  DOI：10.1080/07315724.2002.10719232

  日期：2002.8

  Objective: The purpose of this study was to measure and compare the effect of d-alpha-tocopheryl succuiate (alpha-TS) in modifying radiation-induced chromosomal damage in human normal cells and cancer cells in culture.Methods: Three human normal fibroblast cell lines (GM2149, AG1522 and HF19) and three human cancer cell lines, cervical cancer (HeLa) and ovarian carcinoma cells (OVG1 and SKOV3) were treated with alpha-TS (37.6 AM) 20 hours before 100 cGy gamma-irradiation. After 30 minutes of irradiation, colcemid was added and cells were fixed. One hundred randomly selected metaphase cells were scored for the presence of chromatid gaps and breaks. To study the cellular accumulation of alpha-TS, cells were incubated in the presence of alpha-TS (18.8 and 37.6 AM) for 24 hours, and alpha-TS was extracted with hexane using alpha-tocopheryl acetate as an internal standard. The levels of alpha-TS were determined by HPLC.Results: Results showed that alpha-TS induced chromosomal damage in both human cervical cancer cells and ovarian cancer cells, but not in human normal fibroblasts in culture. In addition, alpha-TS enhanced the level of radiation-induced chromosomal damage in cancer cells, but it protected normal cells against such damage. Both cancer cells and normal cells accumulated similar levels of alpha-TS, suggesting that increased sensitivity of cancer cells to alpha-TS is acquired during transformation.Conclusion: The use of alpha-TS during radiation therapy may improve the efficacy of radiation therapy by enhancing tumor response and decreasing some of the toxicities on normal cells.