(1S,3aR,7aR)-1-{(R)-1-[3-(1-Hydroxy-cyclohexyl)-propoxy]-ethyl}-7a-methyl-octahydro-inden-4-one | 362649-73-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3aR,7aR)-1-{(R)-1-[3-(1-Hydroxy-cyclohexyl)-propoxy]-ethyl}-7a-methyl-octahydro-inden-4-one
• CAS: 362649-73-8
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: KXWYWCHHZSWSSW-FTEYMNFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,3aR,7aR)-1-{(R)-1-[3-(1-Hydroxy-cyclohexyl)-propoxy]-ethyl}-7a-methyl-octahydro-inden-4-one 在 苯基锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 17.0h， 生成 (1S,3aS,7aS)-4-[2-[5-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-1-{(R)-1-[3-(1-trimethylsilanyloxy-cyclohexyl)-propoxy]-ethyl}-octahydro-indene
  参考文献：
  名称：

  Conformationally Restricted Hybrid Analogues of the Hormone 1α,25-Dihydroxyvitamin D3: Design, Synthesis, and Biological Evaluation

  摘要：

  Four new conformationally restricted hybrid analogues of the hormone 1 alpha -25-dihydroxyvitamin D(3) (1,25D3) have been synthesized in a convergent manner by combining enantiomerically pure C,D-ring ketones (-)-15 and (-)-17 with racemic 1-hydroxymethyl A-ring phosphine oxide (+/-)-18. Parent hybrid analogue 6, which combines the calcemia-inactivating la-hydroxymethyl A-ring modification with the antiproliferation-activating 20-epi-22-oxa-25-hydroxydiethyl C,D-ring side chain modification, is comparable in potency to 1,25D3 at the low nM level in inhibiting proliferation in a wide assortment of malignant cell lines in vitro with extremely low calcemic activity in vivo. Surprisingly, both conformationally restricted analogues of 6 (8b and 9b), which incorporate rigidifying units at their 25-hydroxyl side chain termini, retained the desirable antiproliferative, transcriptional. and calcemic activities of the parent compound. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00087-6
• 作为产物：
  描述：

  (1S,3aR,4S,7aS)-1-{(R)-1-[3-(1-Hydroxy-cyclohexyl)-prop-2-ynyloxy]-ethyl}-7a-methyl-octahydro-inden-4-ol 在 palladium on activated charcoal N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 Angstroem MS 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (1S,3aR,7aR)-1-{(R)-1-[3-(1-Hydroxy-cyclohexyl)-propoxy]-ethyl}-7a-methyl-octahydro-inden-4-one
  参考文献：
  名称：

  Conformationally Restricted Hybrid Analogues of the Hormone 1α,25-Dihydroxyvitamin D3: Design, Synthesis, and Biological Evaluation

  摘要：

  Four new conformationally restricted hybrid analogues of the hormone 1 alpha -25-dihydroxyvitamin D(3) (1,25D3) have been synthesized in a convergent manner by combining enantiomerically pure C,D-ring ketones (-)-15 and (-)-17 with racemic 1-hydroxymethyl A-ring phosphine oxide (+/-)-18. Parent hybrid analogue 6, which combines the calcemia-inactivating la-hydroxymethyl A-ring modification with the antiproliferation-activating 20-epi-22-oxa-25-hydroxydiethyl C,D-ring side chain modification, is comparable in potency to 1,25D3 at the low nM level in inhibiting proliferation in a wide assortment of malignant cell lines in vitro with extremely low calcemic activity in vivo. Surprisingly, both conformationally restricted analogues of 6 (8b and 9b), which incorporate rigidifying units at their 25-hydroxyl side chain termini, retained the desirable antiproliferative, transcriptional. and calcemic activities of the parent compound. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00087-6