13β-ethyl-18,19-dinor-17α-pregna-1,3,5(10)-trien-20-yne-3,17β-diol | 14012-72-7

• 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: 13β-ethyl-18,19-dinor-17α-pregna-1,3,5(10)-trien-20-yne-3,17β-diol
• 英文别名: 18-methyl-17α-ethynylestra-1,3,5(10)trien-3,17β-diol；17α-Aethinyl-13β-aethyl-gona-1,3,5(10)-trien-3,17-diol；18-Methylethinylestradiol；(8R,9S,13S,14S,17R)-13-ethyl-17-ethynyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 14012-72-7
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: VDKWHNVDYOVIIX-MJCUULBUSA-N

物化性质

• 沸点：
  468.8±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  levonorgestrel 在 lithium bromide 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以60%的产率得到13β-ethyl-18,19-dinor-17α-pregna-1,3,5(10)-trien-20-yne-3,17β-diol
  参考文献：
  名称：

  (17α,20E/Z)-iodovinyl- and 16α-iodo-18-homoestradiol derivatives: synthesis and evaluation for estrogen receptor imaging

  摘要：

  Three new I-125-radioiodinated estrogens featuring a 13 beta-ethyl instead of the natural 13-methyl group, i.e. 18-homoestradiols, were synthesized and evaluated as potential estrogen receptor imaging agents. The 16 alpha-iodo-18-methylestradiol and the I-125-labeled analog were synthesized from the corresponding 16 beta-bromo analog by the halogen-exchange method. The cis-bromohydrin precursor was obtained by bromination of an estrone enolacetate, followed by epimerization and reduction. The isomeric (17 alpha,20E/Z)-iodovinyl-18-methylestradiols were prepared via the vinyltin intermediates. Treatment of 18-methyl-17 alpha-ethynylestradiol with tri-n-butyltin hydride, in the presence of azobisisobutyronitrile as catalyst and heating at 90-100 degrees C afforded the (17 alpha,20E)-tri-n-butylstannyl isomer as the major product. Changing the catalyst for triethyl borane, at room temperature, mainly gave the 20Z-isomer. The nea I-125-labeled analogs were obtained from their corresponding tin intermediates upon treatment with [I-125]NaI in the presence of H2O2. The 16 alpha-[I-125]iodo- and isomeric (17 alpha,20E/Z)-[I-125]iodovinyl-18-methylestradiols were evaluated for estrogen receptor-mediated uterine uptake in immature female rats. Homologation of the C13-methyl group did improve the uterine uptake of the iodovinyl derivatives, but also increased blood retention, resulting in lower target uptake ratios. In the case of the 16 alpha-iodo analog uterine retention decreased upon C13-homologation. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00084-7

文献信息

• Rufer; Schröder; Gibian, Justus Liebigs Annalen der Chemie, 1971, vol. 752, p. 1 - 13
  作者：Rufer、Schröder、Gibian

  DOI：——

  日期：——
• Preparative chemical methods for aromatization of 19-nor-Δ4-3-oxosteroids
  作者：Pemmaraju N. Rao、James W. Cessac、Hyun K. Kim

  DOI：10.1016/0039-128x(94)90017-5

  日期：1994.11

  Two preparative chemical methods for aromatization of 19-nor-Delta(4)-3-oxosteroids are described. The first method consists of an oxidative aromatization of 19-nor-Delta(4)-3-oxosteroids with iodine-eerie ammonium nitrate in methanol to give a mixture of 3-methoxy ring-A aromatized derivatives consisting of the desired product, the Delta(9,11) derivative, the 6-oxo derivative as well as some ring-A iodinated material. Conversion of this material to a mixture of the 3-methoxy ring-A aromatized derivative and its 6-oxo derivative was achieved by catalytic hydrogenation. Finally, reduction of the 6-oxo function with triethylsilane in trifluoroacetic acid gave the 3-methoxy-17-trifluoroacetate ring-A aromatized derivative as a single product. In the second method, reaction of 19-nor-Delta(4)-3-oxosteroids with copper(II) bromide in acetonitrile at room temperature resulted in aromatic steroids in a single step in excellent yields. The second method was used in the first practical chemical synthesis of a 6-dehydroestrogen from a 19-nor-Delta(4,6)-3-oxosteroid.
• Methods and Compositions Facilitating Entry of Compounds Into Cells
  申请人：Arya Dev Priya

  公开号：US20080226605A1

  公开（公告）日：2008-09-18

  Disclosed are methods and compositions for facilitating entry of compounds to cells. In some forms, the compositions comprise one or more aminoglycosides and one or more lipids. The disclosed compositions can also comprise one or more compounds or compositions. It was discovered that the disclosed compositions increase the efficiency of delivery of compounds into cells. The disclosed compositions and methods increase both delivery into cells and the activity of compounds once delivered into cells. For example, the disclosed methods and compositions can be used to deliver nucleic acids to cells and to thereby increase the activity of such nucleic acids delivered to cells. The disclosed compositions can be used to deliver compounds and compositions to cells in vitro, ex vivo and in vivo. Delivery can be, for example, non-specific, non-directed, non-targeted, specific, directed or targeted.
• (17α,20E/Z)-iodovinyl- and 16α-iodo-18-homoestradiol derivatives: synthesis and evaluation for estrogen receptor imaging
  作者：Hasrat Ali、Jacques Rousseau、Julie Lafrenière、Johan E van Lier

  DOI：10.1016/s0039-128x(99)00084-7

  日期：2000.2

  Three new I-125-radioiodinated estrogens featuring a 13 beta-ethyl instead of the natural 13-methyl group, i.e. 18-homoestradiols, were synthesized and evaluated as potential estrogen receptor imaging agents. The 16 alpha-iodo-18-methylestradiol and the I-125-labeled analog were synthesized from the corresponding 16 beta-bromo analog by the halogen-exchange method. The cis-bromohydrin precursor was obtained by bromination of an estrone enolacetate, followed by epimerization and reduction. The isomeric (17 alpha,20E/Z)-iodovinyl-18-methylestradiols were prepared via the vinyltin intermediates. Treatment of 18-methyl-17 alpha-ethynylestradiol with tri-n-butyltin hydride, in the presence of azobisisobutyronitrile as catalyst and heating at 90-100 degrees C afforded the (17 alpha,20E)-tri-n-butylstannyl isomer as the major product. Changing the catalyst for triethyl borane, at room temperature, mainly gave the 20Z-isomer. The nea I-125-labeled analogs were obtained from their corresponding tin intermediates upon treatment with [I-125]NaI in the presence of H2O2. The 16 alpha-[I-125]iodo- and isomeric (17 alpha,20E/Z)-[I-125]iodovinyl-18-methylestradiols were evaluated for estrogen receptor-mediated uterine uptake in immature female rats. Homologation of the C13-methyl group did improve the uterine uptake of the iodovinyl derivatives, but also increased blood retention, resulting in lower target uptake ratios. In the case of the 16 alpha-iodo analog uterine retention decreased upon C13-homologation. (C) 2000 Elsevier Science Inc. All rights reserved.