2-methylcyclopentanenitrile | 2826-50-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-methylcyclopentanenitrile
• 英文别名: 2-Methyl-cyclopentan-1-carbonsaeure-nitril；2-Methylcyclopentane-1-carbonitrile
• CAS: 2826-50-8
• 化学式: C₇H₁₁N
• 分子量: 109.171
• InChiKey: ZJIHBZDKEFKVBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methylcyclopentanenitrile 在 氢氧化钾 、 乙酰氯 作用下， 以 二乙二醇 为溶剂， 生成 1-(methoxycarbonyl)-2-methylcyclopentane
  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-甲基环戊酮 、 对甲基苯磺酰甲基异腈 在 potassium tert-butylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 以50%的产率得到2-methylcyclopentanenitrile
  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

• [EN] THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE<br/>[FR] COMPOSÉS THÉRAPEUTIQUEMENT ACTIFS ET LEURS MÉTHODES D'UTILISATION
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2015003640A1

  公开（公告）日：2015-01-15

  Provided are compounds useful for treating cancer and methods of treating cancer comprising administering to a subject in need thereof a compound described herein.

  提供了用于治疗癌症的化合物以及治疗癌症的方法，包括向需要的受试者施用本文描述的化合物。
• Heterocyclic Compounds as Janus Kinase Inhibitors
  申请人：Babu Yarlagadda S.

  公开号：US20120149662A1

  公开（公告）日：2012-06-14

  The invention provides compounds of formula (I): or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula (I) and therapeutic methods for suppressing an immune response or treating cancer or a hematologic malignancy using compounds of formula (I).

  本发明提供了以下式子（I）的化合物或其盐，如本文所述。本发明还提供了包含式子（I）化合物的制药组合物，制备式子（I）化合物的方法，用于制备式子（I）化合物的中间体以及使用式子（I）化合物抑制免疫反应或治疗癌症或血液恶性肿瘤的治疗方法。
• NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS FOR PLANT DISEASE CONTROL
  申请人：BAYER CROPSCIENCE AG

  公开号：US20150216172A1

  公开（公告）日：2015-08-06

  The present invention relates to novel isoxazoline carboxamide derivatives, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for control of harmful microorganisms in crop protection and in the protection of materials.

  本发明涉及新型异氧唑羧酰胺衍生物、制备这些化合物的方法、包含这些化合物的组合物以及将其作为生物活性化合物的用途，特别是用于农作物保护和材料保护中的有害微生物的控制。
• THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE
  申请人：AGIOS PHARMACEUTICALS, INC.

  公开号：US20160220572A1

  公开（公告）日：2016-08-04

  Provided are compounds useful for treating cancer and methods of treating cancer comprising administering to a subject in need thereof a compound described herein.

  提供了用于治疗癌症的化合物以及治疗癌症的方法，包括向需要治疗的受试者给予此处所述的化合物。
• EP3088438B1
  申请人：——

  公开号：EP3088438B1

  公开（公告）日：2017-08-09