3β-acetoxy-16-cyano-17-benzyl-16,17-seco-5-androsten-17-one | 639793-24-1

• 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-acetoxy-16-cyano-17-benzyl-16,17-seco-5-androsten-17-one
• 英文别名: [(2S,4aR,4bS,7S,8S,8aR)-8-(cyanomethyl)-4a,7-dimethyl-7-(2-phenylacetyl)-1,2,3,4,4b,5,6,8,8a,9-decahydrophenanthren-2-yl] acetate
• CAS: 639793-24-1
• 化学式: C₂₈H₃₅NO₃
• 分子量: 433.591
• InChiKey: ZQRMVPHZSBYONQ-HCQMQIOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-16-cyano-17-benzyl-16,17-seco-5-androsten-17-one 在 氢氧化钾 作用下， 以 甲醇 、 乙二醇 为溶剂， 反应 1.0h， 生成 3β-hydroxy-D-homo-16-amino-17-phenyl-5,16-androstadien-17a-one
  参考文献：
  名称：

  Synthesis, X-ray crystal structures and biological activity of 16-amino-17-substituted-D-homo steroid derivatives

  摘要：

  Homo derivatives in the androstane and estrane series, 12-19, were synthesized by a fragmentation-cyclization reaction of 16-oximino-17-hydroxy-17-substituted derivatives 3-9, or by cyclization of the corresponding D-seco derivatives 20-26. The structures were confirmed by X-ray analysis of compounds 12 and 16. Preliminary assessment of inhibitory effects of D-homo derivatives from androstane series towards aromatase, 3beta-hydroxysteroid dehydrogenase (3beta-HSD), 17alpha-hydroxylase/C17-20 lyase (P450c17) and 17beta-HSD indicated much lower inhibitory potential compared to previously tested activity of another type of D-modified steroids, namely D-seco derivatives. Also, assessment of potential antiestrogenic activity of derivatives from estrane series showed absence of such an activity. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(03)00097-7
• 作为产物：
  描述：

  3β-hydroxy-16-oximino-5-androsten-17-one 在 lithium 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.0h， 生成 3β-acetoxy-16-cyano-17-benzyl-16,17-seco-5-androsten-17-one
  参考文献：
  名称：

  Synthesis, X-ray crystal structures and biological activity of 16-amino-17-substituted-D-homo steroid derivatives

  摘要：

  Homo derivatives in the androstane and estrane series, 12-19, were synthesized by a fragmentation-cyclization reaction of 16-oximino-17-hydroxy-17-substituted derivatives 3-9, or by cyclization of the corresponding D-seco derivatives 20-26. The structures were confirmed by X-ray analysis of compounds 12 and 16. Preliminary assessment of inhibitory effects of D-homo derivatives from androstane series towards aromatase, 3beta-hydroxysteroid dehydrogenase (3beta-HSD), 17alpha-hydroxylase/C17-20 lyase (P450c17) and 17beta-HSD indicated much lower inhibitory potential compared to previously tested activity of another type of D-modified steroids, namely D-seco derivatives. Also, assessment of potential antiestrogenic activity of derivatives from estrane series showed absence of such an activity. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(03)00097-7

文献信息

• Synthesis and Biological Activity of Some 17a-Substituted Homolactones of Androst-5-ene Derivatives
  作者：Katarina M. Penov Gaši、Srdjan Z. Stojanović、Marija N. Sakač、Evgenija A. Djurendić、János J. Csanádi、Dora Molnar-Gabor、Dušan Lazar、Radmila M. Kovačević

  DOI：10.1135/cccc20051387

  日期：——

  Some new 17a-homolactones were prepared from 3β-hydroxy-16-(hydroxyimino)androst-5-en-17-one (1) as a starting compound, which was transformed first to the corresponding 17α-phenyl and 17α-benzyl derivatives 2 and 3. The structure of compound 3 was confirmed by X-ray structure analysis. Beckmann fragmentation of compounds 2 and 3 yielded 16,17-seco-cyano ketones 4-7, whose reduction with NaBH₄ gave 16,17-seco-cyano alcohols 8-11, whereby the structure of compound 7 was established by X-ray structural analysis. Compounds 8-11 served as the starting compounds for obtaining lactones 12 and 13 in a reaction with potassium hydroxide in ethylene glycol. One-pot procedures were also developed for preparing 17a-homolactones 12, 13 and 16 from the hydroxyimino alcohols 2, 3 and 14. Compounds 12 and 13 showed an inhibitory activity against the enzyme aromatase (63 and 59%, respectively).

  一些新的17a-同型内酯是从3β-羟基-16-(羟肟)雄烯-5-烯-17-酮（1）作为起始化合物制备的，首先转化为相应的17α-苯基和17α-苄基衍生物2和3。化合物3的结构经X射线结构分析确认。化合物2和3的贝克曼分解产生16,17-戊二酮4-7，它们与NaBH4还原后得到16,17-戊二醇8-11，其中化合物7的结构通过X射线结构分析确定。化合物8-11作为起始化合物，通过与乙二醇中的氢氧化钾反应获得内酯12和13。还开发了一锅法制备17a-同型内酯12、13和16，其起始物为羟肝醇2、3和14。化合物12和13显示对芳香化酶的抑制活性分别为63%和59%。