3β-hydroxy-16-(hydroxymethylene)-5α-androstan-17-one | 6174-76-1

• 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-hydroxy-16-(hydroxymethylene)-5α-androstan-17-one
• 英文别名: 3β-hydroxy-16-hydroxymethylidene-5α-androstan-17-one；16-hydroxymethylene-5α-androstan-3β-ol-17-one；3β-hydroxy-16-(hydroxymethylen-(ξ))-5α-androstanone-(17)；3β-Hydroxy-16-(hydroxymethylen-(ξ))-5α-androstanon-(17)；3β-Hydroxy-16-hydroxymethylen-5α-androstan-17-on；(3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-16-(hydroxymethylidene)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 6174-76-1
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: LIURKLQQPKKGSQ-DCHBRCABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-16-(hydroxymethylene)-5α-androstan-17-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (3S,5S,8R,9S,10S,13S,14S,17R)-16,16-Bis-hydroxymethyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  A Convenient Method for the Preparation of 16,16-Bis[hydroxymethyl]-17-hydroxy-steroids and 16,16-Bis[hydroxymethyl]-17-oxo-steroids

  摘要：

  DOI：

  10.1055/s-1985-31152
• 作为产物：
  描述：

  表雄酮 、 甲酸乙酯 在 sodium methylate 、 苯 作用下， 生成 3β-hydroxy-16-(hydroxymethylene)-5α-androstan-17-one
  参考文献：
  名称：

  类固醇和性激素。第153部分。关于一些苯并-过氢-环戊烯-菲衍生物

  摘要：

  通过使丙酮二羧酸酯与甾族酮的α-氧基-亚甲基衍生物缩合并使所得的酚-o，o'-二羧酸脱羧，产生了一些酚，其中在甾族结构上连接了额外的苯环。

  DOI：

  10.1002/hlca.19480310515

文献信息

• Modified steroid hormones—XLVII
  作者：J.M. Allison、D. Burn、F.K. Butcher、M.T. Davies、V. Petrow

  DOI：10.1016/0040-4020(67)85106-8

  日期：1967.1

  A route to pentacyclic steroid derivatives has been developed involving the condensation of steroidal 16-hydroxymethylene-17-ketones with methyl vinyl ketone. The stereochemistry of the products has been investigated.

  已经开发出一种五环类固醇衍生物的方法，该方法涉及将类固醇16-羟基亚甲基-17-酮与甲基乙烯基酮缩合。已经研究了产物的立体化学。
• Interaction of 16-hydroxymethylidene derivatives of androstane and estrone with thiohydrazides of oxamic acids
  作者：I. V. Zavarzin、Ya. S. Antonov、E. I. Chernoburova、M. A. Shchetinina、N. G. Kolotyrkina、A. S. Shashkov

  DOI：10.1007/s11172-013-0379-4

  日期：2013.12

  Reaction of thiohydrazides of oxamic acids with 16-hydroxymethylidene derivatives of androstane and estrone involves the hydroxymethylidene group and leads to thiohydrazones, which undergo heterocyclization to give 16-(1,3,4-thiadiazol-2-yl)-substituted steroids.

  氧草酸硫缩醛与雄甾烷和雌酮的16-羟甲叉衍生物的反应涉及羟甲叉基团，并生成硫缩醛，后者经过杂环化反应生成16-(1,3,4-噻二唑-2-基)-取代的甾体化合物。
• Synthesis and antitumor evaluation of novel hybrids of phenylsulfonylfuroxan and epiandrosterone/dehydroepiandrosterone derivatives
  作者：Yaoqing Huang、Mingming Liu、Lanfang Meng、Pan Feng、Yalan Guo、Minghua Ying、Xiuyan Zhu、Ying Chen

  DOI：10.1016/j.steroids.2015.05.003

  日期：2015.9

  Thirteen novel furoxan-based nitric oxide (NO) releasing hybrids (14a-e, 15a-e, 17b-d) of 16,17-pyrazo-annulated steroidal derivatives were synthesized and evaluated against the MDA-MB-231, HCC1806, SKOV-3, DU145, and HUVEC cell lines for their in vitro anti-proliferative activity. Most of the compounds displayed potent anti-proliferative effects. Among them, 17c exhibited the best activity with IC50 values of 20-1.4 nM against four cell lines (MDA-MB-231, SKOV-3, DU145, and HUVEC), and 1.03 mu M against a tamoxifen resistant breast cancer cell line (HCC1806). Furthermore, five compounds (14a, 15a, 17b-d) were selected to screen for VEGF inhibitory activity. Compounds 15a, 17b,c showed obviously better activity than 2-Methoxyestradiol (2-ME) on reducing levels of VEGF secreted by MDA-MB-231 cell line. In a Capillary-like Tube Formation Assay, compounds 17b,c exhibited a significant suppression of the tubule formation in the concentration of 1.75 nM and 58 nM, respectively. The preliminary SAR showed that steroidal scaffolds with a linker in 3-position were favorable moieties to evidently increase the bioactivities of these hybrids. Overall, these results implied that 17c merited to be further investigated as a promising anti-cancer candidate. (C) 2015 Elsevier Inc. All rights reserved.
• A Convenient Method for the Formation of 16-Methylene-17-ketosteroids
  作者：Gyula Schneider、Irén Vincze、László Hackler、György Dombi

  DOI：10.1055/s-1983-30466

  日期：——
• Pinhey, John T.; Rowe, Bruce A., Australian Journal of Chemistry, 1983, vol. 36, # 4, p. 789 - 794
  作者：Pinhey, John T.、Rowe, Bruce A.

  DOI：——

  日期：——