13-(1,3-dioxolan-2-yl)-3β-hydroxy-16,17-seco-17-norandrost-4-ene-16-nitrile | 1204831-93-5

• 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: 13-(1,3-dioxolan-2-yl)-3β-hydroxy-16,17-seco-17-norandrost-4-ene-16-nitrile
• 英文别名: 2-[(1S,2S,4aS,4bR,7S,10aR)-2-(1,3-dioxolan-2-yl)-7-hydroxy-2,4b-dimethyl-1,3,4,4a,5,6,7,9,10,10a-decahydrophenanthren-1-yl]acetonitrile
• CAS: 1204831-93-5
• 化学式: C₂₁H₃₁NO₃
• 分子量: 345.482
• InChiKey: QZRINDGJRHYPHY-QWSDNZPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  13-(1,3-dioxolan-2-yl)-3β-hydroxy-16,17-seco-17-norandrost-4-ene-16-nitrile 、 乙酸酐 在 吡啶 作用下， 反应 19.0h， 以85%的产率得到3β-acetoxy-13-(1,3-dioxolan-2-yl)-16,17-seco-17-norandrost-4-ene-16-nitrile
  参考文献：
  名称：

  Synthesis and antitumor activity of new d-seco and d-homo androstane derivatives

  摘要：

  Starting from 30-hydroxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), the new 16,17-secoandrostane derivatives 4-9 were synthesized. On the other hand, 3 beta-hydroxy-17-oxa-D-homoandrost-5-ene-16-one (10) yielded the new D-horno derivatives 12, 13 and 15. In vitro antiproliferative activity of selected compounds against three tumor cell lines (human breast ade- nocarcinoma ER+, MCF-7, human breast adenocarcinoma ER-, MDA-MB-231, prostate cancer AR-, PC-3, and normal fetal lung fibroblasts, MRC-5) was evaluated. Compounds 3 and 12 showed strong antiproliferative activity against PC-3 cells, the IC50 values being 2 mu M and 0.55 mu M, respectively. Compounds 6 (10 mu M) and 14 (9 mu M) showed moderate activity against MDA-MB-231 cells. The synthesized compounds 1-3, 5-8, 10 and 12-15 were not toxic to normal fetal lung fibroblasts cells, MRC-5. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.07.007
• 作为产物：
  描述：

  13-(1,3-dioxolan-2-yl)-3-oxo-16,17-seco-17-norandrost-4-ene-16-nitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以31%的产率得到13-(1,3-dioxolan-2-yl)-3α-hydroxy-16,17-seco-17-norandrost-4-ene-16-nitrile
  参考文献：
  名称：

  Synthesis and antitumor activity of new d-seco and d-homo androstane derivatives

  摘要：

  Starting from 30-hydroxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), the new 16,17-secoandrostane derivatives 4-9 were synthesized. On the other hand, 3 beta-hydroxy-17-oxa-D-homoandrost-5-ene-16-one (10) yielded the new D-horno derivatives 12, 13 and 15. In vitro antiproliferative activity of selected compounds against three tumor cell lines (human breast ade- nocarcinoma ER+, MCF-7, human breast adenocarcinoma ER-, MDA-MB-231, prostate cancer AR-, PC-3, and normal fetal lung fibroblasts, MRC-5) was evaluated. Compounds 3 and 12 showed strong antiproliferative activity against PC-3 cells, the IC50 values being 2 mu M and 0.55 mu M, respectively. Compounds 6 (10 mu M) and 14 (9 mu M) showed moderate activity against MDA-MB-231 cells. The synthesized compounds 1-3, 5-8, 10 and 12-15 were not toxic to normal fetal lung fibroblasts cells, MRC-5. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.07.007

文献信息

• Synthesis and antitumor activity of new d-seco and d-homo androstane derivatives
  作者：Evgenija A. Djurendić、Marina P. Zaviš、Marija N. Sakač、Janoš J. Čanadi、Vesna V. Kojić、Gordana M. Bogdanović、Katarina M. Penov Gaši

  DOI：10.1016/j.steroids.2009.07.007

  日期：2009.11

  Starting from 30-hydroxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), the new 16,17-secoandrostane derivatives 4-9 were synthesized. On the other hand, 3 beta-hydroxy-17-oxa-D-homoandrost-5-ene-16-one (10) yielded the new D-horno derivatives 12, 13 and 15. In vitro antiproliferative activity of selected compounds against three tumor cell lines (human breast ade- nocarcinoma ER+, MCF-7, human breast adenocarcinoma ER-, MDA-MB-231, prostate cancer AR-, PC-3, and normal fetal lung fibroblasts, MRC-5) was evaluated. Compounds 3 and 12 showed strong antiproliferative activity against PC-3 cells, the IC50 values being 2 mu M and 0.55 mu M, respectively. Compounds 6 (10 mu M) and 14 (9 mu M) showed moderate activity against MDA-MB-231 cells. The synthesized compounds 1-3, 5-8, 10 and 12-15 were not toxic to normal fetal lung fibroblasts cells, MRC-5. (C) 2009 Elsevier Inc. All rights reserved.