2R-(1S,2-dimethylpropyl)succinic acid 4-tert-butyl ester | 313652-77-6

• 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: 2R-(1S,2-dimethylpropyl)succinic acid 4-tert-butyl ester
• 英文别名: (2R,3S)-3,4-dimethyl-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]pentanoic acid
• CAS: 313652-77-6
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: BOKYBXDWEYWCPI-VHSXEESVSA-N

物化性质

• 沸点：
  335.2±25.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2R-(1S,2-dimethylpropyl)succinic acid 4-tert-butyl ester 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4S)-3-Hydroxymethyl-4,5-dimethyl-hexanoic Acid Tert-butyl Ester
  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：

  (2E)-4-methylpent-2-enoic acid 在 lithium hydroxide 、 copper(I) bromide dimethylsulfide complex 、 双氧水 、 三甲基乙酰氯 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.25h， 生成 2R-(1S,2-dimethylpropyl)succinic acid 4-tert-butyl ester
  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

文献信息

• Alpha 2 Delta Ligands For Fibromyalgia and Other Disorders
  申请人：Dooley David James

  公开号：US20080207755A1

  公开（公告）日：2008-08-28

  This invention relates to a method of treating certain disorders by administering a compound of the formula 1 or a pharmaceutically acceptable salt thereof, wherein: R 1 is hydrogen, straight or branched alkyl of from 1 to 6 carbon atoms or phenyl; and R 2 is straight or branched alkyl of from 4 to 8 carbon atoms, straight or branched alkenyl of from 2 to 8 carbon atoms, cycloalkyl of from 3 to 7 carbon atoms, alkoxy of from 1 to 6 carbon atoms, -alkylcycloalkyl, -alkylalkoxy, -alkyl OH, -alkylphenyl, -alkylphenoxy, or -substituted phenyl. The invention also relates to a method of treating the above disorders by administering the compound (3S, 5R)-3-aminomethyl-5-methyl-octanoic acid.

  本发明涉及一种通过给予公式1化合物或其药学上可接受的盐来治疗某些疾病的方法，其中：R1是氢、1至6个碳原子的直链或支链烷基或苯基；R2是4至8个碳原子的直链或支链烷基、2至8个碳原子的直链或支链烯基、3至7个碳原子的环烷基、1至6个碳原子的烷氧基、-烷基环烷基、-烷基烷氧基、-烷基羟基、-烷基苯基、-烷基苯氧基或-取代苯基。本发明还涉及一种通过给予化合物(3S, 5R)-3-氨甲基-5-甲基-辛酸来治疗上述疾病的方法。
• ALPHA 2 DELTA LIGANDS FOR FIBROMYALGIA AND OTHER DISORDERS
  申请人：Dooley James David

  公开号：US20070027212A1

  公开（公告）日：2007-02-01

  This invention relates to a method of treating a disorder selected from OCD, agoraphobia, agoraphobia without history of panic disorder, specific phobia, social phobia, PTSD, restless legs syndrome, premenstrual dysphoric disorder, hot flashes, and fibromyalgia by administering a compound of the formula 1 or a pharmaceutically acceptable salt thereof, wherein: R 1 is hydrogen, straight or branched alkyl of from 1 to 6 carbon atoms or phenyl; and R 2 is straight or branched alkyl of from 4 to 8 carbon atoms, straight or branched alkenyl of from 2 to 8 carbon atoms, cycloalkyl of from 3 to 7 carbon atoms, alkoxy of from 1 to 6 carbon atoms, -alkylcycloalkyl, -alkylalkoxy, -alkyl OH, -alkylphenyl, -alkylphenoxy, or -substituted phenyl. The invention also relates to a method of treating the above disorders by administering the compound (3S,5R)-3-Aminomethyl-5-methyl-octanoic acid.

  本发明涉及通过给予式1化合物或其药学上可接受的盐治疗选自强迫症、广场恐惧症、无惊恐障碍史的广场恐惧症、特定恐惧症、社交恐惧症、创伤后应激障碍、不宁腿综合症、月经前期失调症、潮热和纤维肌痛的方法，其中：R1是氢、1至6个碳原子的直链或支链烷基或苯基；R2是4至8个碳原子的直链或支链烷基、2至8个碳原子的直链或支链烯基、3至7个碳原子的环烷基、1至6个碳原子的烷氧基、-烷基环烷基、-烷基烷氧基、-烷基-OH、-烷基苯基、-烷基苯氧基或-取代苯基。本发明还涉及通过给予化合物(3S,5R)-3-氨甲基-5-甲基-辛酸治疗上述疾病的方法。
• US7189747B2
  申请人：——

  公开号：US7189747B2

  公开（公告）日：2007-03-13
• US7164034B2
  申请人：——

  公开号：US7164034B2

  公开（公告）日：2007-01-16
• US7381747B2
  申请人：——

  公开号：US7381747B2

  公开（公告）日：2008-06-03