3-ethoxy-16,17-seco-3,5-androstadiene-16,17-dinitrile | 1382358-16-8

• 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: 3-ethoxy-16,17-seco-3,5-androstadiene-16,17-dinitrile
• CAS: 1382358-16-8
• 化学式: C₂₁H₂₈N₂O
• 分子量: 324.466
• InChiKey: IGHCBIKIJIVKSI-FCMAGTKHSA-N

反应信息

• 作为反应物：
  描述：

  3-ethoxy-16,17-seco-3,5-androstadiene-16,17-dinitrile 在 丙酮 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 为溶剂， 以47%的产率得到3-oxo-16,17-seco-4,6-androstadiene-16,17-dinitrile
  参考文献：
  名称：

  Steroidal carbonitriles as potential aromatase inhibitors

  摘要：

  Estrogens, responsible for the growth of hormone-dependant breast cancer are biosynthesized from androgens involving aromatase enzyme in the last rate limiting step. Inhibition of aromatase is an efficient approach for the prevention and treatment of breast cancer. Novel 4-phenylthia derivatives (2, 3 and 7) have been synthesized as aromatase inhibitors. The synthesized compounds (2,3 and 7) exhibited noticeable enzyme inhibiting activity. Kinetics study of these compounds (2, 3, and 7) showed negligible inhibition of the enzyme under conditions conducive for irreversible inhibition of the enzyme. Introduction of unsaturation at C-4, C-1 & 4 or C-4 & 6 (compounds 5, 9 and 11) was observed to not be an effective strategy for entrancing aromatase inhibiting activity in 17-oxo-16 beta-carbonitrile derivatives. The D-seco derivatives (13-15 and 17) having unsaturation at C-4, C-1 & 4 or C-4 & 6 along with carbonitrile function in ring-D showed complete loss of aromatase inhibiting activity. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.04.010
• 作为产物：
  描述：

  3β-hydroxy-16,17-secoandrost-5-ene-16,17a-dinitrile 在 aluminum isopropoxide 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 环己酮 、 甲苯 为溶剂， 反应 2.0h， 生成 3-ethoxy-16,17-seco-3,5-androstadiene-16,17-dinitrile
  参考文献：
  名称：

  Steroidal carbonitriles as potential aromatase inhibitors

  摘要：

  Estrogens, responsible for the growth of hormone-dependant breast cancer are biosynthesized from androgens involving aromatase enzyme in the last rate limiting step. Inhibition of aromatase is an efficient approach for the prevention and treatment of breast cancer. Novel 4-phenylthia derivatives (2, 3 and 7) have been synthesized as aromatase inhibitors. The synthesized compounds (2,3 and 7) exhibited noticeable enzyme inhibiting activity. Kinetics study of these compounds (2, 3, and 7) showed negligible inhibition of the enzyme under conditions conducive for irreversible inhibition of the enzyme. Introduction of unsaturation at C-4, C-1 & 4 or C-4 & 6 (compounds 5, 9 and 11) was observed to not be an effective strategy for entrancing aromatase inhibiting activity in 17-oxo-16 beta-carbonitrile derivatives. The D-seco derivatives (13-15 and 17) having unsaturation at C-4, C-1 & 4 or C-4 & 6 along with carbonitrile function in ring-D showed complete loss of aromatase inhibiting activity. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.04.010