(1S,4S,7aS)-1-cetyl-7a-methyloctahydro-1H-inden-4-yl acetate | 154314-43-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,4S,7aS)-1-cetyl-7a-methyloctahydro-1H-inden-4-yl acetate
• 英文别名: [(1S,3aR,4S,7aS)-1-acetyl-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] acetate
• CAS: 154314-43-9
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: VWMKUBRHWMCHSS-ZOBORPQBSA-N

物化性质

• 熔点：
  <20 °C
• 沸点：
  314.2±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4S,7aS)-1-cetyl-7a-methyloctahydro-1H-inden-4-yl acetate 在 sodium hydroxide 、 重铬酸吡啶 、 三氟甲磺酸三甲基硅酯 、 苯基锂 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  概念上新的激素1alpha，25-dihydroxyvitamin D（3）的20-epi-22-oxa砜类似物：合成和生物学评估。

  摘要：

  制备了具有天然1alpha，3beta-羟基基团但缺乏天然激素1alpha，25-dihydroxyvitamin D（3）（25）的25-羟基基团的新C，D环侧链改性砜4a和特点。新颖的合成功能包括：（1）在伯-仲双甲硅烷基醚中间体中仅对伯甲硅烷基醚进行化学选择氧化，以及（2）平滑还原醚化而不受相邻磺酰基的干扰。砜4a，但不是它的1beta，3alpha-非对映异构体4b，在体外具有强大的抗增殖和转录活性，但在体内则是非消钙的。尽管砜4a的设计类似于Leo Pharmaceutical Co.的KH-1060（3），但被分解代谢酶识别，

  DOI：

  10.1021/jm000215j
• 作为产物：
  描述：

  <1R-<1α(S^*),3aβ,4α,7aα>>-4-acetoxyoctahydro-α,7a-dimethyl-1H-indene-1-acetaldehyde 在 aluminum oxide 、 potassium permanganate 、 对甲苯磺酸 作用下， 以 丙酮 、 苯 为溶剂， 反应 2.0h， 生成 (1S,4S,7aS)-1-cetyl-7a-methyloctahydro-1H-inden-4-yl acetate
  参考文献：
  名称：

  Total synthesis of biologically active 20S-hydroxyvitamin D3

  摘要：

  A total synthetic strategy of 20S-hydroxyvitamin D3 [20S-(OH)D3] involving modified synthesis of key intermediates 7 and 12, Grignard reaction to stereoselectively generate 20S-OH and Wittig-Horner coupling to establish D3 framework, was completed in 16 steps with an overall yield of 0.4%. The synthetic 20S-(OH)D3 activated vitamin D receptor (VDR) and initiated the expression of downstream genes. In addition, 20S-(OH)D3 showed similar inhibitory potency as calcitriol [1,25(OH)(2)D3] on proliferation of melanoma cells. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.09.009

文献信息

• Chemical synthesis, biological activities and action on nuclear receptors of 20S(OH)D3, 20S,25(OH)2D3, 20S,23S(OH)2D3 and 20S,23R(OH)2D3
  作者：Pawel Brzeminski、Adrian Fabisiak、Radomir M. Slominski、Tae-Kang Kim、Zorica Janjetovic、Ewa Podgorska、Yuwei Song、Mohammad Saleem、Sivani B. Reddy、Shariq Qayyum、Yuhua Song、Robert C. Tuckey、Venkatram Atigadda、Anton M. Jetten、Rafal R. Sicinski、Chander Raman、Andrzej T. Slominski

  DOI：10.1016/j.bioorg.2022.105660

  日期：2022.4

  as indicated by molecular modeling. They functioned as substrates for CYP27B1 with enzymatic activity being the highest towards 20S,25(OH)2D3 and the lowest towards 20S(OH)D3. In conclusion, defining new routes for large scale synthesis of endogenously produced D3-hydroxy derivatives by pathways initiated by CYP11A1 opens an exciting era to analyze their common and differential activities in vivo, particularly

  维生素 D 3 (D 3 ) 羟基 (OH) 代谢物的化学合成新途径和更有效的途径，包括 20 S (OH)D 3、 20 S ,23 S (OH) 2 D 3和 20 S ,25(OH) 2 D 3，由 CYP11A1 在人体中内源性产生，以及 20 S ,23 R (OH) 2 D 3成立。生物学评价表明，这些化合物在抑制细胞增殖和诱导细胞分化方面表现出相似的特性，但在数量上存在细微差别。它们显示出对T细胞免疫活性的重叠和差异影响。它们还显示了与核受体的相似相互作用，所有类固醇激活维生素 D、肝 X、视黄酸孤儿和芳基烃受体在功能测定中，也如分子模型所示。它们充当 CYP27B1 的底物，酶活性对 20 S ,25(OH) 2 D 3最高，对 20 S (OH)D 3最低. 总之，定义通过 CYP11A1 启动的途径大规模合成内源性 D 3 -羟基衍生物的新途径开启了一个激动人心的时代，
• A facile stereoselective route to a C/D-ring synthon for 20-epi-22-oxavitamin D3 analogues
  作者：Susumi Hatakeyama、Tatsuhiko Ikeda、Hiroshi Irie、Chino Izumi、Hisato Mori、Kohsei Uenoyama、Hidetoshi Yamada、Mugio Nishizawa

  DOI：10.1039/c39950001959

  日期：——

  An efficient method for the preparation of a C/D-ring synthon for 20-epi-22-oxavitamin D3 analogues is developed based on Me3SiOSO2CF3 catalysed reductive etherification of a ketone with an alkoxytrimethylsilane in the presence of triethylsilane.

  在三乙基硅烷存在下，基于Me 3 SiOSO 2 CF 3催化的酮与烷氧基三甲基硅烷的还原性醚化作用，开发了一种有效的方法来制备20-表-22-恶维他命D 3类似物的C / D环合成子。
• Antiproliferative, low-calcemic, fluorinated sulfone analogs of 1α,25-dihydroxyvitamin D3: Chemical synthesis and biological evaluation
  作者：Aimee R. Usera、Patrick M. Dolan、Thomas W. Kensler、Gary H. Posner

  DOI：10.1016/j.bmc.2007.05.051

  日期：2007.8

  Novel fluorinated sulfone analogs of the hormone 1 alpha,25-dihydroxyvitamm D-3 have been designed and synthesized in order to study the biological effects of fluorine incorporation at the terminus of the C,D-ring side chain. Although biologically active 26,27-hexafluorinated 1 alpha,25-dihydroxyvitamin D-3 analogs have been synthesized previously, this investigation reports the first successful fluorinated series in which trifluoromethyl sulfone analogs present a favorable biological profile. This study shows that two new analogs featuring incorporation of a synthetically simple single trifluoromethyl sulfone group have significantly increased antiproliferative activity while causing desirably low in vivo calciuria relative to that of calcitriol. Incorporation of additional fluorines, as in a perfluorobutyl analog, results in a loss of antiproliferative activity. (c) 2007 Elsevier Ltd. All rights reserved.