2'-(1,1-dimethylethyl)-2'H-androst-16-eno[17,16-c]pyrazole-3β-ol | 1312597-42-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2'-(1,1-dimethylethyl)-2'H-androst-16-eno[17,16-c]pyrazole-3β-ol
• CAS: 1312597-42-4
• 化学式: C₂₄H₃₈N₂O
• 分子量: 370.579
• InChiKey: CVUJBALKUQRGCB-CFYKOPIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  27.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.05
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2'-(1,1-dimethylethyl)-2'H-androst-16-eno[17,16-c]pyrazole-3β-ol 、 呋咱氮氧化物供体 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以13%的产率得到3β-{[5-oxido-4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]oxy}-2'H-2'-(1,1-dimethylethyl)-androst-16-eno[17,16-c]pyrazole
  参考文献：
  名称：

  Synthesis and antitumor evaluation of novel hybrids of phenylsulfonylfuroxan and epiandrosterone/dehydroepiandrosterone derivatives

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2015.05.003
• 作为产物：
  描述：

  表雄酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 2'-(1,1-dimethylethyl)-2'H-androst-16-eno[17,16-c]pyrazole-3β-ol
  参考文献：
  名称：

  Synthesis and VEGF inhibitory activity of 16,17-pyrazo-annulated steroids

  摘要：

  Eight 16,17-pyrazo-annulated steroidal derivatives were synthesized and evaluated in vitro vascular endothelial growth factor (VEGF) inhibitory activity with 2-methoxyestradiol (2-ME) as the reference compound. Most of the compounds showed potent VEGF inhibitory activity with EC50 values of micromolar or submicromolar range. Among them, the compounds 3 and 8 exhibited similar EC50 values and obviously better TI values compared with 2-ME. (C) 2010 Ying Chen. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.12.043