{(1R,3S)-3-tert-Butoxycarbonylamino-5-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl}-carbamic acid tert-butyl ester | 874635-41-3

• 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: {(1R,3S)-3-tert-Butoxycarbonylamino-5-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl}-carbamic acid tert-butyl ester
• CAS: 874635-41-3
• 化学式: C₃₇H₆₂N₂O₅
• 分子量: 614.91
• InChiKey: JUPLKYQPTSDAON-DARLDLPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.77
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  96.89
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {(1R,3S)-3-tert-Butoxycarbonylamino-5-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以55%的产率得到
  参考文献：
  名称：

  Versatile synthesis and biological evaluation of 1,3-diamino-substituted 1α,25-dihydroxyvitamin D3 analogues

  摘要：

  A concise route to 1 alpha,3 beta-diamino-25-hydroxy-3-deoxyvitamin D-3 (5) and 1 beta,3 alpha-diamino-25-hydroxy-3-deoxyvitamin D, (6) has been developed starting from (R)- or (S)-carvone for the construction of the modified A-ring fragments. The conversion of the hydroxyl group to amine function with complete inversion of the configuration was efficiently accomplished by Mitsunobu reaction using phthalimide as nucleophile or activation of the hydroxyl group as mesylate followed by reaction with NaN3. Diamino 5 and 6 as well as monoamino 3, 4 X and 31 vitamin D3 derivatives have shown poor binding to VDR compared with 1 alpha,25-dihydroxyvitamin D3. The most active compound in the inhibition of MCF-7 cell proliferation and HL 60 cell differentiation was 1 alpha-amino analogue 3. Also, very low in vivo calcemic effects of derivatives 3 and 4 were found. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.009
• 作为产物：
  描述：

  (3S,5S)-1-ethynyl-5-hydroxy-2-methyl-3-phthalimidocyclohex-1-ene 在 喹啉 、 Lindlar's catalyst 、 copper(l) iodide 、 bis(triphenylphosphine) palladium (Il) acetate 、 四丁基氟化铵 、 氢气 、 碳酸氢钠 、 二乙胺 、 三苯基膦 、 甲胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 79.83h， 生成 {(1R,3S)-3-tert-Butoxycarbonylamino-5-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Versatile synthesis and biological evaluation of 1,3-diamino-substituted 1α,25-dihydroxyvitamin D3 analogues

  摘要：

  A concise route to 1 alpha,3 beta-diamino-25-hydroxy-3-deoxyvitamin D-3 (5) and 1 beta,3 alpha-diamino-25-hydroxy-3-deoxyvitamin D, (6) has been developed starting from (R)- or (S)-carvone for the construction of the modified A-ring fragments. The conversion of the hydroxyl group to amine function with complete inversion of the configuration was efficiently accomplished by Mitsunobu reaction using phthalimide as nucleophile or activation of the hydroxyl group as mesylate followed by reaction with NaN3. Diamino 5 and 6 as well as monoamino 3, 4 X and 31 vitamin D3 derivatives have shown poor binding to VDR compared with 1 alpha,25-dihydroxyvitamin D3. The most active compound in the inhibition of MCF-7 cell proliferation and HL 60 cell differentiation was 1 alpha-amino analogue 3. Also, very low in vivo calcemic effects of derivatives 3 and 4 were found. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.009