3-(hydroxymethyl)-5-methyl-hexanoic acid 1,1-dimethyl ester | 157422-29-2

• 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: 3-(hydroxymethyl)-5-methyl-hexanoic acid 1,1-dimethyl ester
• 英文别名: tert-butyl (3S)-3-(hydroxymethyl)-5-methylhexanoate
• CAS: 157422-29-2
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: PHBGVZFOAQLNJP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(hydroxymethyl)-5-methyl-hexanoic acid 1,1-dimethyl ester 在 镍 正丁基锂 、 sodium azide 、 氢溴酸 、 氢气 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二甲基亚砜 为溶剂， -78.0~60.0 ℃ 、330.95 kPa 条件下， 反应 30.33h， 生成 (4S)-isobutyl-(3S)-methylpyrrolidin-2-one
  参考文献：
  名称：

  Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein

  摘要：

  Pregabalin exhibits robust activity in preclinical assays indicative of potential antiepileptic, anxiolytic, and antihyperalgesic clinical efficacy. It binds with high affinity to the alpha(2)-delta subunit of voltage-gated calcium channels and is a substrate of the system L neutral amino acid transporter. A series of pregabalin analogues were prepared and evaluated for their alpha(2)-delta binding affinity as demonstrated by their ability to inhibit binding of [H-3]gabapentin to pig brain membranes and for their potency to inhibit the uptake of [H-3]leucine into CHO cells, a measure of their ability to compete with the endogenous substrate at the system L transporter. Compounds were also assessed in vivo for their ability to promote anxiolytic, analgesic, and anticonvulsant actions. These studies suggest that distinct structure activity relationships exist for alpha(2)-delta binding and system L transport inhibition. However, both interactions appear to play an important role in the in vivo profile of these compounds.

  DOI：

  10.1021/jm049762l
• 作为产物：
  描述：

  (S)-2-isobutylsuccinic acid 4-O-t-butyl ester 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.45h， 以97%的产率得到3-(hydroxymethyl)-5-methyl-hexanoic acid 1,1-dimethyl ester
  参考文献：
  名称：

  GABA and L-glutamic acid analogs for antiseizure treatment

  摘要：

  该化合物的化学式为，其中R1是直链或支链烷基基团，含有1至6个碳原子，苯基，或含有3至6个碳原子的环烷基；R2是氢或甲基；R3是氢，甲基或羧基；该化合物在治疗癫痫障碍方面具有用途。公开了制备该化合物的方法。还公开了在合成该化合物过程中制备的中间体。

  公开号：

  US06359169B1

文献信息

• GABA and L-glutamic acid analogs for antiseizure treatment
  申请人：Northwestern University

  公开号：US06359169B1

  公开（公告）日：2002-03-19

  A compound of the formula wherein R1 is a straight or branched alkyl group having from 1 to 6 carbon atoms, phenyl, or cycloalkyl having from 3 to 6 carbon atoms; R2 is hydrogen or methyl; and R3 is hydrogen, methyl or carboxyl; which is useful in the treatment of seizure disorders. Processes are disclosed for the preparation of the compound. Intermediates prepared during the synthesis of the compound are also disclosed.

  该化合物的化学式为，其中R1是直链或支链烷基基团，含有1至6个碳原子，苯基，或含有3至6个碳原子的环烷基；R2是氢或甲基；R3是氢，甲基或羧基；该化合物在治疗癫痫障碍方面具有用途。公开了制备该化合物的方法。还公开了在合成该化合物过程中制备的中间体。
• ANTI-INFLAMMATORY COMPOUNDS IN COMBINATION WITH HYDROGEN FOR THE TREATMENT OF INFLAMMATION
  申请人：SKYVIEW ENTERPRISE LTD.

  公开号：US20150140090A1

  公开（公告）日：2015-05-21

  A composition for treating inflammation and pain, including a hydrogen-generating compound in an amount that increases the amount of hydrogen in an individual and has an anti-inflammatory effect. A composition for treating inflammation and pain, including synergistically effective amounts of pregabalin and lactulose. A method of treating inflammation and pain, by administering a composition comprising a hydrogen-generating compound to an individual in an amount that increases the amount of hydrogen in the individual and has an anti-inflammatory effect.
• US9545415B2
  申请人：——

  公开号：US9545415B2

  公开（公告）日：2017-01-17
• US9925204B2
  申请人：——

  公开号：US9925204B2

  公开（公告）日：2018-03-27
• Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein
  作者：Thomas R. Belliotti、Thomas Capiris、I. Victor Ekhato、Jack J. Kinsora、Mark J. Field、Thomas G. Heffner、Leonard T. Meltzer、Jacob B. Schwarz、Charles P. Taylor、Andrew J. Thorpe、Mark G. Vartanian、Lawrence D. Wise、Ti Zhi-Su、Mark L. Weber、David J. Wustrow

  DOI：10.1021/jm049762l

  日期：2005.4.1

  Pregabalin exhibits robust activity in preclinical assays indicative of potential antiepileptic, anxiolytic, and antihyperalgesic clinical efficacy. It binds with high affinity to the alpha(2)-delta subunit of voltage-gated calcium channels and is a substrate of the system L neutral amino acid transporter. A series of pregabalin analogues were prepared and evaluated for their alpha(2)-delta binding affinity as demonstrated by their ability to inhibit binding of [H-3]gabapentin to pig brain membranes and for their potency to inhibit the uptake of [H-3]leucine into CHO cells, a measure of their ability to compete with the endogenous substrate at the system L transporter. Compounds were also assessed in vivo for their ability to promote anxiolytic, analgesic, and anticonvulsant actions. These studies suggest that distinct structure activity relationships exist for alpha(2)-delta binding and system L transport inhibition. However, both interactions appear to play an important role in the in vivo profile of these compounds.