6α-n-pentylandrost-4-ene-3,17-dione | 59251-70-6

• 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
• 英文名称: 6α-n-pentylandrost-4-ene-3,17-dione
• 英文别名: 6alpha-Pentyl-4-androstene-3,17-dione；(6S,8R,9S,10R,13S,14S)-10,13-dimethyl-6-pentyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 59251-70-6
• 化学式: C₂₄H₃₆O₂
• 分子量: 356.549
• InChiKey: VIEGBWJBDLNCHK-QEDSVCCZSA-N

物化性质

• 沸点：
  486.5±45.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6α-n-pentylandrost-4-ene-3,17-dione 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 生成 methyl 3-[(3S,3aS,5aS,6R,8S,9aS,9bS)-3-hydroxy-3a,6-dimethyl-7-oxo-8-pentyl-1,2,3,4,5,5a,8,9,9a,9b-decahydrocyclopenta[a]naphthalen-6-yl]propanoate
  参考文献：
  名称：

  Secoandrostansäurenal对映体前列腺素类似物-II：6-戊基-4-nor-3,5-seco-androstan-3-säuren

  摘要：

  描述了对映体四氢-PGA 1类似物48的合成。另外homoacid 50，其pentanor类似物39及其差向异构体51，所述6-脱氧化合物13和16以及内酯类14，53，56和68制备为密切相关的化合物48。简单的雄烷烷衍生物用作合成的起始材料。关键中间体是4、32和63。

  DOI：

  10.1016/0040-4020(75)80159-1
• 作为产物：
  描述：

  3β,17β-diacetoxy-5,6α-epoxy-5α-androstane 在 chromium(VI) oxide 、 甲醇 、 sodium hydroxide 、 硫酸 作用下， 生成 6α-n-pentylandrost-4-ene-3,17-dione
  参考文献：
  名称：

  Secoandrostansäurenal对映体前列腺素类似物-II：6-戊基-4-nor-3,5-seco-androstan-3-säuren

  摘要：

  描述了对映体四氢-PGA 1类似物48的合成。另外homoacid 50，其pentanor类似物39及其差向异构体51，所述6-脱氧化合物13和16以及内酯类14，53，56和68制备为密切相关的化合物48。简单的雄烷烷衍生物用作合成的起始材料。关键中间体是4、32和63。

  DOI：

  10.1016/0040-4020(75)80159-1

文献信息

• Time-Dependent Inactivation of Aromatase by 6-Alkylandrosta-1,4-diene-3,17-diones. Effects of Length and Configuration of the 6-Alkyl Group
  作者：Mitsuteru Numazawa、Mariko Oshibe、Satoshi Yamaguchi、Mii Tachibana

  DOI：10.1021/jm950720u

  日期：1996.1.1

  structure-activity relationship of varying the 6-n-alkyl substituents (C-1--C-7) to the time-dependent inactivation activity. All of the inhibitors synthesized were powerful to good competitive inhibitors of aromatase, with apparent Ki's ranging from 4.7 to 54 nM. The 6beta-ethyl (4b) and 6beta-n-pentyl (4e) compounds were the most potent among them (Ki = 4.7 and 5.0 nM for 4b and 4e, respectively).

  合成了一系列6α-和6β-烷基雄甾烯-1,4-二烯-3,17-二酮（3和4），并作为人类胎盘微粒体中芳香化酶的时间依赖性灭活剂进行了评估，以了解其结构活性关系。将6-正烷基取代基（C-1--C-7）改变为随时间变化的灭活活性。合成的所有抑制剂均是芳香酶的良好竞争抑制剂，其表观Ki范围为4.7至54 nM。6beta-乙基（4b）和6beta-n-戊基（4e）化合物是其中最有效的化合物（4b和4e的Ki分别为4.7和5.0 nM）。在一系列的6-α-烷基甾族化合物中，在6-位具有C-1--C-4的抑制剂3a-d以及6个α-正庚基（3g）化合物没有。相反，在6β-烷基甾族化合物系列中，只有甲基类似物4a会以时间依赖性方式使芳香化酶失活，而在C-6beta处具有两个以上碳原子的其他烷基类固醇则没有。底物雄烯二酮可防止失活，并且在每种情况下均未观察到L-半胱氨酸对失活的显着影响。这些结果以及使用P
• Numazawa, Mitsuteru; Oshibe, Mariko, Steroids, 1995, vol. 60, # 8, p. 576 - 581
  作者：Numazawa, Mitsuteru、Oshibe, Mariko

  DOI：——

  日期：——
• 6-Alkylandrosta-4,6-diene-3,17-diones and their 1,4,6-triene analogs as aromatase inhibitors
  作者：Mitsuteru Numazawa、Mariko Oshibe、Satoshi Yamaguchi

  DOI：10.1016/s0039-128x(97)86814-6

  日期：1997.8

  Two series of 6-alkylandrosta-4,6-diene-3,17-diones (5) and their 1,4,6-triene analogs 6 were synthesized as aromatase inhibitors to gain insight into the structure-activity relationship between varying the 6-n-alkyl substituents (C-1-C-7) and inhibitory activity. All of the steroids synthesized were extremely powerful competitive inhibitors of aromatase in human placental microsomes, with apparent K-i values for the 6-alkyl-4,6-diene steroids 5 ranging from 17 to 36 nM and with those for the 1,4,6-triene steroids 6 ranging from 2.5 to 58 nM. The 6-ethyl-1,4,6-triene compound 6b (K-i = 2.5 nM) was the most potent inhibitor among them. The 6-alkyl-1,4,6-triene steroids 6, except for the 6-methyl analog 6a, had higher affinity for aromatase than the natural substrate androstenedione (K-m = 24 nM), and their inhibitory activities were more potent than the corresponding 4,6-diene steroids 5. In a series of the 4,6-diene steroids 5, compounds 5c-f with the n-alkyl chain substituents (C-3 to C-6) also had slightly higher affinity than androstenedione for aromatase. All of the 1,4,6-triene steroids 6 inactivated aromatase in a time-dependent manner, with k(inact) values ranging from 0.021 to 0.074 min(-1); in contrast, the 4,6-diene analogs 5 did not. The inactivation was prevented by androstenedione, and no significant effect of L-cysteine on the inactivation was observed in each case. These results indicate that the length of the n-alkyl substituent at C-6 of androsta-1,4,6-triene-3,17-dione (6h), rather than its 4,6-diene analog 5h, plays a critical role in tight binding to the active site of aromatase. No significant correlation was observed between affinity for the enzyme and the inactivation ability of the 6-alkyl-1,4,6-trienes. (C) 1997 by Elsevier Science Inc.
• Secoandrostansäuren als enantiomere prostaglandin-analoga—II
  作者：M. Baumgarth、K. Irmscher

  DOI：10.1016/0040-4020(75)80159-1

  日期：1975.1

  A synthesis of the enantiomeric tetrahydro-PGA1 analogue 48 is described. In addition the homoacid 50, its pentanor analogue 39 and its epimer 51, the 6-deoxy compounds 13 and 16 as well as the lactones 14, 53, 56 and 68 were prepared as compounds closely related to 48. Simple androstane derivatives served as starting materials for the syntheses. Key intermediates were 4, 32 and 63.

  描述了对映体四氢-PGA 1类似物48的合成。另外homoacid 50，其pentanor类似物39及其差向异构体51，所述6-脱氧化合物13和16以及内酯类14，53，56和68制备为密切相关的化合物48。简单的雄烷烷衍生物用作合成的起始材料。关键中间体是4、32和63。