(1S,6R,7R,9S)-9-methoxy-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4,3,0]nonan-2-one | 1181662-20-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,6R,7R,9S)-9-methoxy-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4,3,0]nonan-2-one
• 英文别名: (1R,3S,3aS,7aR)-3-methoxy-1-[(2R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 1181662-20-3
• 化学式: C₂₁H₃₈O₄
• 分子量: 354.53
• InChiKey: IZXOLVGINVSLTQ-PNLWMVSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,6R,7R,9S)-9-methoxy-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4,3,0]nonan-2-one 在 正丁基锂 、 D(+)-10-樟脑磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 7.17h， 生成 15α-methoxy-1α,25-dihydroxyvitamin D3
  参考文献：
  名称：

  New C15-Substituted Active Vitamin D₃

  摘要：

  C15-Substituted 1 alpha,25-dihydroxyvitamin D-3 analogs were synthesized for the first time to investigate the effects of the modified CD-ring on biological activity concerning the agonistic positioning of helix-3 and helix-12 of the vitamin D receptor (VDR). X-ray cocrystallographic analysis proved that 0.6 angstrom shifts of the CD-ring and shrinking of the side chain were necessary to maintain the position of the 25-hydroxy group for proper interaction with helix-12. The 15-hydroxy-16-ene derivative showed higher binding affinity for hVDR than the natural hormone.

  DOI：

  10.1021/ol200828s
• 作为产物：
  描述：

  (1R,2S,6S)-7-acetoxy-2-[(tert-butyldimethylsilyl)oxy]-6-methylbicyclo[4.3.0]non-7-ene 在 正丁基锂 、 四丙基高钌酸铵 、 烯丙基甲基碳酸酯 、 palladium on carbon 、 四丁基氟化铵 、 氢气 、 三正丁基甲氧基锡 、 palladium diacetate 、 sodium hydride 、 二异丁基氢化铝 、 magnesium 、 N-甲基吗啉氧化物 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 107.67h， 生成 (1S,6R,7R,9S)-9-methoxy-7-[(R)-6-(methoxymethoxy)-6-methylheptan-2-yl]-6-methylbicyclo[4,3,0]nonan-2-one
  参考文献：
  名称：

  New C15-Substituted Active Vitamin D₃

  摘要：

  C15-Substituted 1 alpha,25-dihydroxyvitamin D-3 analogs were synthesized for the first time to investigate the effects of the modified CD-ring on biological activity concerning the agonistic positioning of helix-3 and helix-12 of the vitamin D receptor (VDR). X-ray cocrystallographic analysis proved that 0.6 angstrom shifts of the CD-ring and shrinking of the side chain were necessary to maintain the position of the 25-hydroxy group for proper interaction with helix-12. The 15-hydroxy-16-ene derivative showed higher binding affinity for hVDR than the natural hormone.

  DOI：

  10.1021/ol200828s

文献信息

• New C15-Substituted Active Vitamin D₃
  作者：Kanako Shindo、Go Kumagai、Masashi Takano、Daisuke Sawada、Nozomi Saito、Hiroshi Saito、Shinji Kakuda、Ken-ichiro Takagi、Eiji Ochiai、Kyohei Horie、Midori Takimoto-Kamimura、Seiichi Ishizuka、Kazuya Takenouchi、Atsushi Kittaka

  DOI：10.1021/ol200828s

  日期：2011.6.3

  C15-Substituted 1 alpha,25-dihydroxyvitamin D-3 analogs were synthesized for the first time to investigate the effects of the modified CD-ring on biological activity concerning the agonistic positioning of helix-3 and helix-12 of the vitamin D receptor (VDR). X-ray cocrystallographic analysis proved that 0.6 angstrom shifts of the CD-ring and shrinking of the side chain were necessary to maintain the position of the 25-hydroxy group for proper interaction with helix-12. The 15-hydroxy-16-ene derivative showed higher binding affinity for hVDR than the natural hormone.