醋酸妊娠双烯醇酮酯杂质M | 14279-42-6

• 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
• 中文名称: 醋酸妊娠双烯醇酮酯杂质M
• 英文名称: 3β-acetoxy-5α,6α-epoxypregn-16-ene-20-one
• 英文别名: 3β-acetoxy-5α,6α-epoxy-16-pregnen-20-one；3β-acetoxy-5α,6α-epoxypregn-16-en-20-one；3β-acetoxy-5,6-epoxy-16-pregnen-20-one；5,6α-Epoxy-16-dehydro-pregnenolon-acetat；[(1S,2R,5S,7R,9S,11S,12S,16S)-15-acetyl-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-14-en-5-yl] acetate
• CAS: 14279-42-6
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: UYNAMKNNUDDKNG-ZFNWETCLSA-N

物化性质

• 熔点：
  196-197.5 °C
• 沸点：
  481.5±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  醋酸妊娠双烯醇酮酯杂质M 在 chromium(VI) oxide 、 盐酸 、 硫酸 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 6α,16α-Dimethyl-17α-hydroxy-progesteron-acetat
  参考文献：
  名称：

  6,16-二甲基化的甾体。二。6,16α-二甲基-17α-羟基羟孕酮的合成研究。

  摘要：

  DOI：

  10.1021/jm00334a031
• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 silica gel 、 间氯过氧苯甲酸 作用下， 反应 1.5h， 以91.75%的产率得到醋酸妊娠双烯醇酮酯杂质M
  参考文献：
  名称：

  Ghosh, Pranab; Subba, Raju, Journal of the Indian Chemical Society, 2012, vol. 89, # 12, p. 1733 - 1735

  摘要：

  DOI：

文献信息

• Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate
  作者：João F.S. Carvalho、M. Manuel Cruz Silva、M. Luisa Sá e Melo

  DOI：10.1016/j.tet.2009.01.100

  日期：2009.4

  Fast generation of epoxides from the corresponding homoallylic and allylic steroidal olefins was developed by using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) as oxidant suspended in acetonitrile (CH3CN) at reflux temperature. The protocol involves the use of a safe readily available oxidant along with an easy work-up, which renders the process very efficient. Selective 4,5- and 5,6-epoxidations

  通过在回流温度下使用悬浮在乙腈（CH 3 CN）中的双（双过氧邻苯二甲酸酯）六水合镁（MMPP）作为氧化剂，可以从相应的均烯丙基和烯丙基甾体烯烃快速生成环氧化物。该方案涉及使用安全易得的氧化剂以及易于后处理的方法，这使该过程非常有效。据报道类固醇的选择性4，5-和5，6-环氧化。其中，Δ的高立体选择性环氧化5 -B去甲胆甾烷达到了。而且，该方法对5，6-位是化学选择性的，可用于环A烯酮的环氧化。
• Synthesis and cytotoxic effect on cancer cell lines and macrophages of novel progesterone derivatives having an ester or a carbamate function at C-3 and C-17
  作者：Alejandra Chávez-Riveros、Mariana Garrido、María Teresa Ramírez Apan、Armando Zambrano、Mario Díaz、Eugene Bratoeff

  DOI：10.1016/j.ejmech.2014.06.008

  日期：2014.7

  In this study we report the cytotoxic effect on human cancer cells of two series of novel progesterone derivatives; the first containing an aromatic ester (8a-e) or a carbamate functions both linked to C-3 (9a -e) on the pregn-4,16-diene-6,20-dione skeleton. In the second series, both functional groups (ester and carbamate) are bound to C-17 on the pregn-4,6-diene-3,20-dione scaffold (13a-e and 14a-e). The panel cancer cell lines used in this study were the following: PC-3 (human prostate cancer cell line), MCF-7 (human breast cancer cell line), HCT-15 (human colon cancer cell line) and J774 (noncancerous murine macrophages) for comparison.The results from this study showed that steroid 14a, having a carbamate function at C-17, was the most potent against PC-3 cell line (96.6%) while 8c and 8e showed much higher cytotoxic activity (100%) for MCF-7 cell line. Finally, compounds 8c and 14a displayed selective properties towards tumor cell lines than noncancerous murine macrophages. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Uyanik, Cavit; Malay, Aslihan; Hanson, James R., Journal of Chemical Research, 2006, # 7, p. 417 - 419
  作者：Uyanik, Cavit、Malay, Aslihan、Hanson, James R.、Hitchcock, Peter B.、Tiryakioglu, Serpil

  DOI：——

  日期：——
• Effect of new hybrids based on 5,16-pregnadiene scaffold linked to an anti-inflammatory drug on the growth of a human astrocytoma cell line (U373)
  作者：Mariana Garrido、Aliesha González-Arenas、Ignacio Camacho-Arroyo、Marisa Cabeza、Belén Alcaraz、Eugene Bratoeff

  DOI：10.1016/j.ejmech.2015.01.048

  日期：2015.3

  In spite of the fact that anaplastic astrocytoma is an uncommon disease, very often the pathology of this disease is associated with lethal effects due to the late diagnosis and unspecific treatments. This paper reports the synthesis and the biological effect on the growth of U373 cell line (human anaplastic astrocytoma) of new hybrid compounds based on 5,16-pregnadiene scaffold linked to an anti-inflammatory drug (6a-e). Moreover, we also determined the cell growth effect of five non-steroidal anti-inflammatory drugs (naproxen, ibuprofen, ketoprofen, indomethacin and sulindac) as well as the free steroidal alcohol 5. The results from this study indicated that sulindac as well as compound 5 decreased the number of U373 cells at different concentrations. However, when an anti-inflammatory drug was bound to the steroidal structure (5), the resulting compounds (6a-e) showed an enhanced biological effect with exception of hybrid 6c. Furthermore, derivative 6e (sulindac hybrid) did not allow cell growth during six days of experiment at a concentration of 10 mu M. The overall data indicated that these molecules showed an anti-proliferative activity on anaplastic astrocytoma cell line. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Oxidation of natural targets by dioxiranes. Oxyfunctionalization of steroids
  作者：Paolo Bovicelli、Paolo Lupattelli、Enrico Mincione、Teresa Prencipe、Ruggero Curci

  DOI：10.1021/jo00033a053

  日期：1992.3