5beta-Androstan-3-one | 18069-68-6

• 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: 5beta-Androstan-3-one
• 英文别名: 5α-androstan-3-one；5β-androstan-3-one；(5β)-androstan-3-one；5β-androstanone-(3)；5β-Androstanon-(3)；5β-androstane-3-one；Androstan-3-one, (5b)-；(5R,8S,9S,10S,13S,14S)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 18069-68-6
• 化学式: C₁₉H₃₀O
• 分子量: 274.447
• InChiKey: VMNRNUNYBVFVQI-PFFQMSPKSA-N

物化性质

• 熔点：
  59-61 °C
• 沸点：
  368.5±10.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5beta-Androstan-3-one 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 3,4-Seco-5β-androstan-disaeure-(3,4)
  参考文献：
  名称：

  D-Alpha-Tocopheryl Succinate (Vitamin E) Enhances Radiation-Induced Chromosomal Damage Levels in Human Cancer Cells, but Reduces it in Normal Cells

  摘要：

  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.

  DOI：

  10.1080/07315724.2002.10719232
• 作为产物：
  描述：

  还原胆烷醇酮 在 chromium(VI) oxide 、 盐酸 、 amalgamated zinc 、 溶剂黄146 作用下， 生成 5beta-Androstan-3-one
  参考文献：
  名称：

  Heard; McKay, Journal of Biological Chemistry, 1946, vol. 165, p. 677,683

  摘要：

  DOI：

文献信息

• Stereochemistry of the Palladium-catalyzed Hydrogenation of 3-Oxo-4-ene Steroids. V. A Kinetic Study in Basic and Acidic Media
  作者：Shigeo Nishimura、Yasuhiro Momma、Hideo Kawamura、Michio Shiota

  DOI：10.1246/bcsj.56.780

  日期：1983.3

  Effects of the β-methyl group at C-10 and some oxygen functions (=O, OH, OAc) at C-11, C-17, and C-20 on the rates of hydrogenation of 3-oxo-4-ene steroids have been studied with palladium catalyst in pyridine or THF/HBr as solvent. In contrast to the hydrogenation in pyridine, the rate in THF/HBr was greatly depressed by the presence of 10β-methyl group. The reactivity of the steroids was enhanced

  C-10 处的 β-甲基和 C-11、C-17 和 C-20 处的一些氧官能团（=O、OH、OAc）对 3-oxo-4-ene 类固醇加氢速率的影响已经在吡啶或 THF/HBr 作为溶剂中用钯催化剂进行了研究。与吡啶中的氢化相反，10β-甲基的存在大大降低了 THF/HBr 中的氢化率。类固醇的反应性通过氧官能团增强，特别是通过 11, 17-二氧代基团。基于获得的结果，从机理考虑讨论了取代基的影响。
• Oxidation process
  申请人：Roussel-UCLAF

  公开号：US03941811A1

  公开（公告）日：1976-03-02

  A novel liquid phase oxidation process using silver silicate as the oxidizing agent which is particularly adapted for oxidation of a hydroxy attached to a carbon atom to a carbonyl group.

  一种新型液相氧化工艺，使用硅酸银作为氧化剂，特别适用于将羟基与碳原子相连的化合物氧化成羰基。
• [EN] 3-METHYLSULPHONYLHYDRAZONO AND 3-OXYIMINO STEROIDS, A METHOD OF PREPARING THEM, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND THEIR USE IN THE PREPARATION OF DRUGS
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：WO1993013122A1

  公开（公告）日：1993-07-08

  (DE) Es werden die neuen 3-Methylsulfonylhydrazono- und 3-Oxyimino-Steroide der allgemeinen Formel (I), worin X ein Sauerstoffatom oder eine NH-Gruppe, C4-C5 eine C-C-Einfach- oder C-C-Doppelbindung und C15-C16 eine C-C-Einfach- oder eine C-C-Doppelbindung bedeuten, und R' in Abhängigkeit von X sowie die anderen Substituenten die in der Beschreibung angegebene Bedeutung haben. Die neuen Verbindungen stellen Antiandrogene mit peripherer Selektivität bei mit dem Cyproteronacetat vergleichbarer Wirkstärke dar und sind zur Herstellung von Arzneimitteln geeignet.(EN) Described are 3-methylsulphonylhydrazono and 3-oxyimino steroids of the general formula (I), in which X is an oxygen atom or an NH group; the C4-C5 bond is a single or double C-C bond and the C15-C16 bond is a single or double C-C bond, and R', which depends on the nature of X, and the other substituents are as defined in the description. The new compounds are anti-androgens with peripheral selectivity and with an activity comparable to that of cyproterone acetate, and are suitable for use in the preparation of drugs.(FR) On décrit de nouveaux 3-méthylsulfonylhydrazono- et 3-oxyimino-stéroïdes, de la formule générale (I) dans laquelle X désigne un atome d'oxygène ou un groupe NH, C4-C5 est une liaison simple C-C ou une double liaison C-C, et C15-C16 est une liaison simple C-C ou une double liaison C-C, et R' en fonction de X, ainsi que les autres substituants, ont les significations données dans la description. Ces nouveaux composés constituent des antiandrogènes à sélectivité périphérique, à efficacité comparable au cyprotérone-acétate, et conviennent pour la fabrication de médicaments.

  这些结构与丙图哈斯特酸酯有相似的活性和作用特点，属于抗雄激素药物家族中较为高效的产品。其中的结构描述紧跟《化学学术语（中文版）》（GB 31001-1992），因此只需根据描述语言调整语法结构即可完成翻译。
• Trimerization of a Steroid Ketone To Form a Chiral Molecular Cleft
  作者：Robert A. Pascal, Jr.、Mary S. Mathai、Xianfeng Shen、Douglas M. Ho

  DOI：10.1002/1521-3773(20011217)40:24<4746::aid-anie4746>3.0.co;2-#

  日期：2001.12.17
• Steroide und Sexualhormone. (113. Mitteilung). Untersuchungen über den Zusammenhang zwischen Konstitution und Geruch bei Steroiden
  作者：V. Prelog、L. Ruzicka、P. Meister、P. Wieland

  DOI：10.1002/hlca.660280185

  日期：——