1α,3β-dihydroxy-20(S)-(2(R)-hydroxy-3-methylbutyloxy)pregna-5,7,16-triene | 210219-67-3

• 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: 1α,3β-dihydroxy-20(S)-(2(R)-hydroxy-3-methylbutyloxy)pregna-5,7,16-triene
• 英文别名: 1alpha,3beta-dihydroxy-20(S)-{2(R)-hydroxy-3-methylbutyloxy}pregna-5,7,16-triene；(1S,3R,9S,10R,13S,14S)-17-[(1S)-1-[(2R)-2-hydroxy-3-methylbutoxy]ethyl]-10,13-dimethyl-2,3,4,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthrene-1,3-diol
• CAS: 210219-67-3
• 化学式: C₂₆H₄₀O₄
• 分子量: 416.601
• InChiKey: JSUBQZOOBPPVTD-YTZCVETDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1α,3β-dihydroxy-20(S)-(2(R)-hydroxy-3-methylbutyloxy)pregna-5,7,16-triene 以 乙醇 为溶剂， 反应 0.03h， 以12%的产率得到1α,3β-dihydroxy-20(S)-((2R)-2-hydroxy-3-methylbutyloxy)-9,10-secopregna-5,7,10(19),16-tetraene
  参考文献：
  名称：

  Novel vitamin D3 antipsoriatic antedrugs: 16-En-22-oxa-1α,25-(OH)2D3 analogs

  摘要：

  A series of 16-en-22-oxa-derivatives of vitamin D-3 based on the structure of maxacalcitol (2) were prepared. Maxacalcitol is currently used topically for the treatment of psoriasis and is recognized as the most successful antedrug of natural vitamin D-3 because it retains the original antiproliferative activity of calcitriol without increased calcemic activity. We introduced 16-olefinic functionality to accelerate the oxidative metabolism of the drug in liver, presumed to be essential for the reduction of calcemic activity, and modified the side-chain moiety by placing the 22-oxygen on the more labile allylic carbon center. Novel 22-oxa analogs (7a-i), carrying either the 24-alkynyl bond or 24-hydroxy functionality in addition to the 16-double bond were synthesized and their pharmacokinetics were evaluated. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.034
• 作为产物：
  描述：

  1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-{2(R)-hydroxy-3-methylbutyloxy}pregna-5,7,16-triene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以12.0 mg的产率得到1α,3β-dihydroxy-20(S)-(2(R)-hydroxy-3-methylbutyloxy)pregna-5,7,16-triene
  参考文献：
  名称：

  Novel vitamin D3 antipsoriatic antedrugs: 16-En-22-oxa-1α,25-(OH)2D3 analogs

  摘要：

  A series of 16-en-22-oxa-derivatives of vitamin D-3 based on the structure of maxacalcitol (2) were prepared. Maxacalcitol is currently used topically for the treatment of psoriasis and is recognized as the most successful antedrug of natural vitamin D-3 because it retains the original antiproliferative activity of calcitriol without increased calcemic activity. We introduced 16-olefinic functionality to accelerate the oxidative metabolism of the drug in liver, presumed to be essential for the reduction of calcemic activity, and modified the side-chain moiety by placing the 22-oxygen on the more labile allylic carbon center. Novel 22-oxa analogs (7a-i), carrying either the 24-alkynyl bond or 24-hydroxy functionality in addition to the 16-double bond were synthesized and their pharmacokinetics were evaluated. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.034

文献信息

• 16-ENE-VITAMIN D DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20020193616A1

  公开（公告）日：2002-12-19

  The compound of the formula (24): 1 wherein R 9 R 10 may be the same or different and each represent a hydrogen atom or a protecting group.

  化学式（24）的化合物：其中R9和R10可以相同或不同，且均表示氢原子或保护基。
• 16-ene-vitamin D derivatives
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20020032340A1

  公开（公告）日：2002-03-14

  A compound having the formula (4): wherein 1 X is oxygen or sulfur, R 9 and R 10 are each a hydrogen or a protecting group, and R 11 is an aliphatic hydrocarbon, a —COR 12 group where R 12 is alkyl, aryl or alkoxy, or a group of formula 2 wherein R 5 and R 6 are each hydrogen or hydroxyl, m is 1 to 4, and n is 0-2.

  一个化合物的化学式为(4)，其中1X是氧或硫，R9和R10分别是氢或保护基团，R11是脂肪烃、—COR12基团（其中R12是烷基、芳基或烷氧基）或化学式2中的基团（其中R5和R6分别是氢或羟基，m为1到4，n为0-2）。
• 16-ENE-vitamin D derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US06326503B1

  公开（公告）日：2001-12-04

  A compound having the formula (4): wherein X is oxygen or sulfur, R9 and R10 are each a hydrogen or a protecting group, and R11 is an aliphatic hydrocarbon, a —COR12 group where R12 is alkyl, aryl or alkoxy, or a group of formula wherein R5 and R6 are each hydrogen or hydroxyl, m is 1 to 4, and n is 0-2.

  化合物的化学式为（4）：其中X为氧或硫，R9和R10分别为氢或保护基，R11为脂肪烃、-COR12基团，其中R12为烷基、芳基或烷氧基，或者为式中的基团，其中R5和R6分别为氢或羟基，m为1至4，n为0-2。
• US06184398B2
  申请人：——

  公开号：——

  公开（公告）日：——
• US6184398B1
  申请人：——

  公开号：US6184398B1

  公开（公告）日：2001-02-06