9,21-Dihydroxyryanodine | 106821-51-6

• 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: 9,21-Dihydroxyryanodine
• 英文别名: [(1R,2R,3R,6S,7S,9S,10S,11S,12R,13S,14R)-2,3,6,9,11,13,14-heptahydroxy-3-(hydroxymethyl)-7,10-dimethyl-11-propan-2-yl-15-oxapentacyclo[7.5.1.01,6.07,13.010,14]pentadecan-12-yl] 1H-pyrrole-2-carboxylate
• CAS: 106821-51-6
• 化学式: C₂₅H₃₅NO₁₁
• 分子量: 525.553
• InChiKey: DHVVNSKDLZXOQU-WKOGGBBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  213
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  9,21-Dihydroxyryanodine 在 sodium periodate 、 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 [(1R,6S,7S,9S,10S,11S,12R,13S,14R)-6,9,11,13,14-pentahydroxy-7,10-dimethyl-3-oxo-11-propan-2-yl-15-oxapentacyclo[7.5.1.01,6.07,13.010,14]pentadecan-12-yl] 1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Ryanodine Action at Calcium Release Channels. 2. Relation to Substituents of the Cyclohexane Ring

  摘要：

  Ryanodine (1) and dehydroryanodine (2) are equipotent probes for the ryanodine receptor (ryr) of calcium release channels and differ only in 9(eq)-methyl for 1 and 9,21-methylene for 2. Ryanoids 1 and 2 are used here to prepare novel modifications of the cyclohexane substituents to determine their effects on ryr activity and selectivity. 10-0xo-1 when reacted with carbonyl and other reagents gave 13 C-10 derivatives including the epi-amine and epi-4-azidobenzoyl hydrazide as a candidate affinity probe. Four derivatives of 2 included the Delta(8)-10-hydroxy and Delta(8)-10-oxo compounds. Defunctionalization of the cyclohexane ring of 2 or its 4,6-ethylboronate was achieved :in part by controlled periodate oxidation of the 9,21-diol to the 21-nor-9-oxo compounds. These in turn provided access to the 9(ax)- and 9(eq)-hydroxy derivatives and to the 21-nor-10-deoxy-9-oxo compound which was converted to 21-nor-10-deoxy-1 and 10-deoxy-2 along with the epimeric 10-deoxy-9-hydroxy compounds. Ryanoids of similar potency to 1 as inhibitors of [H-3](-1) binding in mouse brain, rabbit skeletal muscle, and canine ventricle ryr preparations sind in a rat cardiac contractility assay (inhibition of mechanical response to electrical stimulation) are epi-l and the 10-epi-amino, 10-epi-methoxyamino, and 20-epi-azidobenzoyl hydrazide derivatives and 10-deoxydehydroryanodine. With a few exceptions the potency of the ryanoids at the cardiac ryr correlates well with their inhibition of cardiac contractility, indicating that the activity is associated with stabilizing the calcium release channel in a subconducting state, thereby uncoupling the excitation-contraction process.

  DOI：

  10.1021/jm950712d
• 作为产物：
  描述：

  9,21-二氢-鱼尼丁-3-(1H-吡咯-2-羧酸) 在 吡啶 、 四氧化锇 作用下， 反应 12.0h， 以72%的产率得到9,21-Dihydroxyryanodine
  参考文献：
  名称：

  Ryanodine Action at Calcium Release Channels. 2. Relation to Substituents of the Cyclohexane Ring

  摘要：

  Ryanodine (1) and dehydroryanodine (2) are equipotent probes for the ryanodine receptor (ryr) of calcium release channels and differ only in 9(eq)-methyl for 1 and 9,21-methylene for 2. Ryanoids 1 and 2 are used here to prepare novel modifications of the cyclohexane substituents to determine their effects on ryr activity and selectivity. 10-0xo-1 when reacted with carbonyl and other reagents gave 13 C-10 derivatives including the epi-amine and epi-4-azidobenzoyl hydrazide as a candidate affinity probe. Four derivatives of 2 included the Delta(8)-10-hydroxy and Delta(8)-10-oxo compounds. Defunctionalization of the cyclohexane ring of 2 or its 4,6-ethylboronate was achieved :in part by controlled periodate oxidation of the 9,21-diol to the 21-nor-9-oxo compounds. These in turn provided access to the 9(ax)- and 9(eq)-hydroxy derivatives and to the 21-nor-10-deoxy-9-oxo compound which was converted to 21-nor-10-deoxy-1 and 10-deoxy-2 along with the epimeric 10-deoxy-9-hydroxy compounds. Ryanoids of similar potency to 1 as inhibitors of [H-3](-1) binding in mouse brain, rabbit skeletal muscle, and canine ventricle ryr preparations sind in a rat cardiac contractility assay (inhibition of mechanical response to electrical stimulation) are epi-l and the 10-epi-amino, 10-epi-methoxyamino, and 20-epi-azidobenzoyl hydrazide derivatives and 10-deoxydehydroryanodine. With a few exceptions the potency of the ryanoids at the cardiac ryr correlates well with their inhibition of cardiac contractility, indicating that the activity is associated with stabilizing the calcium release channel in a subconducting state, thereby uncoupling the excitation-contraction process.

  DOI：

  10.1021/jm950712d

文献信息

• Ryanodine Action at Calcium Release Channels. 2. Relation to Substituents of the Cyclohexane Ring
  作者：Phillip R. Jefferies、Peter J. Gengo、Michael J. Watson、John E. Casida

  DOI：10.1021/jm950712d

  日期：1996.1.1

  Ryanodine (1) and dehydroryanodine (2) are equipotent probes for the ryanodine receptor (ryr) of calcium release channels and differ only in 9(eq)-methyl for 1 and 9,21-methylene for 2. Ryanoids 1 and 2 are used here to prepare novel modifications of the cyclohexane substituents to determine their effects on ryr activity and selectivity. 10-0xo-1 when reacted with carbonyl and other reagents gave 13 C-10 derivatives including the epi-amine and epi-4-azidobenzoyl hydrazide as a candidate affinity probe. Four derivatives of 2 included the Delta(8)-10-hydroxy and Delta(8)-10-oxo compounds. Defunctionalization of the cyclohexane ring of 2 or its 4,6-ethylboronate was achieved :in part by controlled periodate oxidation of the 9,21-diol to the 21-nor-9-oxo compounds. These in turn provided access to the 9(ax)- and 9(eq)-hydroxy derivatives and to the 21-nor-10-deoxy-9-oxo compound which was converted to 21-nor-10-deoxy-1 and 10-deoxy-2 along with the epimeric 10-deoxy-9-hydroxy compounds. Ryanoids of similar potency to 1 as inhibitors of [H-3](-1) binding in mouse brain, rabbit skeletal muscle, and canine ventricle ryr preparations sind in a rat cardiac contractility assay (inhibition of mechanical response to electrical stimulation) are epi-l and the 10-epi-amino, 10-epi-methoxyamino, and 20-epi-azidobenzoyl hydrazide derivatives and 10-deoxydehydroryanodine. With a few exceptions the potency of the ryanoids at the cardiac ryr correlates well with their inhibition of cardiac contractility, indicating that the activity is associated with stabilizing the calcium release channel in a subconducting state, thereby uncoupling the excitation-contraction process.