methyl 1-(2-propenyl)-2-methylcyclopentanecarboxylate | 153579-97-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 1-(2-propenyl)-2-methylcyclopentanecarboxylate
• 英文别名: Methyl 2-methyl-1-prop-2-enylcyclopentane-1-carboxylate
• CAS: 153579-97-6
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: UBBVSEJAOSKVLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 1-(2-propenyl)-2-methylcyclopentanecarboxylate 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 (5α,6α)-6-methyl-2-oxaspiro<4.4>nonan-1-one 、 (5α,6β)-6-methyl-2-oxaspiro<4.4>nonan-1-one
  参考文献：
  名称：

  .alpha.-Spirocyclopentyl- and .alpha.-spirocyclopropyl-.gamma.-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant .alpha.,.alpha.-disubstituted .gamma.-butyrolactones

  摘要：

  To further study the putative gamma-butyrolactone site of the GABA(A)/chloride channel complex, constrained derivatives of convulsant and anticonvulsant alpha,alpha-disubstituted gamma-butyrolactones (alpha-spirocyclopropyl- and alpha-spirocyclopentyl-gamma-butyrolactones) were synthesized and evaluated biologically. Most of the spirocyclopropyl agents were anticonvulsants when tested against pentylenetetrazole-induced seizures in mice. These agents effectively displaced (35)[S]-tert-butylbicyclophosphorothionate ((35)[S] -TBPS), a ligand for the picrotoxin binding site of the GABA(A)/chloride channel, from rat neuronal membranes and affected the GABA-mediated current in hippocampal neurons. The monomethyl-substituted spirocyclopropyl agent with a methyl group cis to the carbonyl (15) potentiates GABA-induced current whereas the trans derivative (16) blocks the current. The only anticonvulsant in the spirocyclopentyl series was the unsubstituted spirocyclopentyl compound 2. All the other substituted spirocyclopentyl targets were inactive in vivo at the highest dose tested except for convulsant 9, which has a trans 2,5-dimethyl-substituted cyclopentyl ring. All the spirocyclopentyl derivatives displaced (35)[S]-TBPS from rat neuronal membranes very effectively, and they also all potentiated GABA-induced chloride current except for convulsant 9 which blocked the current. From the data obtained in this investigation, it appears that when the volume occupied above and below the lactone ring is as large as that occupied by spirocyclopentyl agent 9, convulsant activity is observed. Groups with less volume in these areas either are inactive in the behavioral test or have anticonvulsant activity. When bound to the GABA(A)/chloride channel, the larger molecules may stabilize the closed state of the channel whereas the smaller molecules may stabilize the open state.

  DOI：

  10.1021/jm00028a011
• 作为产物：
  描述：

  2-甲基-环戊烷羧酸 在 乙酰氯 、 lithium diisopropyl amide 作用下， 生成 methyl 1-(2-propenyl)-2-methylcyclopentanecarboxylate
  参考文献：
  名称：

  .alpha.-Spirocyclopentyl- and .alpha.-spirocyclopropyl-.gamma.-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant .alpha.,.alpha.-disubstituted .gamma.-butyrolactones

  摘要：

  To further study the putative gamma-butyrolactone site of the GABA(A)/chloride channel complex, constrained derivatives of convulsant and anticonvulsant alpha,alpha-disubstituted gamma-butyrolactones (alpha-spirocyclopropyl- and alpha-spirocyclopentyl-gamma-butyrolactones) were synthesized and evaluated biologically. Most of the spirocyclopropyl agents were anticonvulsants when tested against pentylenetetrazole-induced seizures in mice. These agents effectively displaced (35)[S]-tert-butylbicyclophosphorothionate ((35)[S] -TBPS), a ligand for the picrotoxin binding site of the GABA(A)/chloride channel, from rat neuronal membranes and affected the GABA-mediated current in hippocampal neurons. The monomethyl-substituted spirocyclopropyl agent with a methyl group cis to the carbonyl (15) potentiates GABA-induced current whereas the trans derivative (16) blocks the current. The only anticonvulsant in the spirocyclopentyl series was the unsubstituted spirocyclopentyl compound 2. All the other substituted spirocyclopentyl targets were inactive in vivo at the highest dose tested except for convulsant 9, which has a trans 2,5-dimethyl-substituted cyclopentyl ring. All the spirocyclopentyl derivatives displaced (35)[S]-TBPS from rat neuronal membranes very effectively, and they also all potentiated GABA-induced chloride current except for convulsant 9 which blocked the current. From the data obtained in this investigation, it appears that when the volume occupied above and below the lactone ring is as large as that occupied by spirocyclopentyl agent 9, convulsant activity is observed. Groups with less volume in these areas either are inactive in the behavioral test or have anticonvulsant activity. When bound to the GABA(A)/chloride channel, the larger molecules may stabilize the closed state of the channel whereas the smaller molecules may stabilize the open state.

  DOI：

  10.1021/jm00028a011

文献信息

• .alpha.-Spirocyclopentyl- and .alpha.-spirocyclopropyl-.gamma.-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant .alpha.,.alpha.-disubstituted .gamma.-butyrolactones
  作者：Eileen M. Peterson、Kun Xu、Katherine D. Holland、Ann C. McKeon、Steven M. Rothman、James A. Ferrendelli、Douglas F. Covey

  DOI：10.1021/jm00028a011

  日期：1994.1

  To further study the putative gamma-butyrolactone site of the GABA(A)/chloride channel complex, constrained derivatives of convulsant and anticonvulsant alpha,alpha-disubstituted gamma-butyrolactones (alpha-spirocyclopropyl- and alpha-spirocyclopentyl-gamma-butyrolactones) were synthesized and evaluated biologically. Most of the spirocyclopropyl agents were anticonvulsants when tested against pentylenetetrazole-induced seizures in mice. These agents effectively displaced (35)[S]-tert-butylbicyclophosphorothionate ((35)[S] -TBPS), a ligand for the picrotoxin binding site of the GABA(A)/chloride channel, from rat neuronal membranes and affected the GABA-mediated current in hippocampal neurons. The monomethyl-substituted spirocyclopropyl agent with a methyl group cis to the carbonyl (15) potentiates GABA-induced current whereas the trans derivative (16) blocks the current. The only anticonvulsant in the spirocyclopentyl series was the unsubstituted spirocyclopentyl compound 2. All the other substituted spirocyclopentyl targets were inactive in vivo at the highest dose tested except for convulsant 9, which has a trans 2,5-dimethyl-substituted cyclopentyl ring. All the spirocyclopentyl derivatives displaced (35)[S]-TBPS from rat neuronal membranes very effectively, and they also all potentiated GABA-induced chloride current except for convulsant 9 which blocked the current. From the data obtained in this investigation, it appears that when the volume occupied above and below the lactone ring is as large as that occupied by spirocyclopentyl agent 9, convulsant activity is observed. Groups with less volume in these areas either are inactive in the behavioral test or have anticonvulsant activity. When bound to the GABA(A)/chloride channel, the larger molecules may stabilize the closed state of the channel whereas the smaller molecules may stabilize the open state.