1α,3α,5α-(1-aminomethyl)-(3,5-dimethylcyclohexane)acetic acid | 723732-37-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1α,3α,5α-(1-aminomethyl)-(3,5-dimethylcyclohexane)acetic acid
• CAS: 723732-37-4
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: RITSSYUURQCBAD-DOFRTFSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.32
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 1α,3α,5α-(1-aminomethyl)-(3,5-dimethylcyclohexane)acetic acid 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 C₁₆H₂₉NO₄
  参考文献：
  名称：

  Oxadiazolone bioisosteres of pregabalin and gabapentin

  摘要：

  A series of oxadiazolone bioisosteres of pregabalin 1 and gabapentin 2 were prepared, and several were found to exhibit similar potency for the alpha(2)-delta subunit of voltage-gated calcium channels. Oxadiazolone 9 derived from 2 achieved low brain uptake but was nevertheless active in models of osteoarthritis. The high clearance associated with compound 9 was postulated to be a consequence of efflux by OAT and/or OCT, and was attenuated on co-administration with cimetidine or probenecid. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.10.101
• 作为产物：
  描述：

  顺式-3,5-二甲基环己酮 在 镍 盐酸 、 四丁基氟化铵 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 生成 1α,3α,5α-(1-aminomethyl)-(3,5-dimethylcyclohexane)acetic acid
  参考文献：
  名称：

  Investigation into the preferred conformation of gabapentin for interaction with its binding site on the α2δ subunit of a calcium channel

  摘要：

  A series of conformationally restricted Gabapentin analogues has been synthesised and used to propose the preferred conformation of Gabapentin for it to bind to the alpha(2) delta subunit of a calcium channel. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10002-6

文献信息

• BRANCHED CHAIN AMINO ACID-DEPENDENT AMINOTRANSFERASE INHIBITORS AND THEIR USE IN THE TREATMENT OF DIABETIC RETINOPATHY
  申请人：Warner-Lambert Company LLC

  公开号：EP1157000B1

  公开（公告）日：2005-11-02
• [EN] BRANCHED CHAIN AMINO ACID-DEPENDENT AMINOTRANSFERASE INHIBITORS AND THEIR USE IN THE TREATMENT OF DIABETIC RETINOPATHY<br/>[FR] INHIBITEURS D'AMINOTRANSFERASE ACIDES AMINES-DEPENDANTE A CHAINE RAMIFIEE, ET LEUR UTILISATION DANS LE CADRE DU TRAITEMENT DE LA RETINOPATHIE DIABETIQUE
  申请人：WARNER LAMBERT CO

  公开号：WO2001042191A1

  公开（公告）日：2001-06-14

  The present invention is directed to a method for the prophylactic and therapeutic treatment of diabetic retinopathy. The method involves the administration of an inhibitor of formulae (I), (II) and (III) of the branch chain amino acid-dependent aminotransferase (BCAT) pathway to an animal, such as a mammal, in particular a human, in an amount sufficient to treat the retina for diabetic retinopathy prophylactically or therapeutically. The present invention is also directed to several novel inhibitors of formula (IV) of the BCAT pathway. In formulae (I-IV), n, m, X and R1-R13 have the meanings given in the description.
• [EN] ACTIVE SUBSTANCE COMBINATION<br/>[FR] COMBINAISON DE SUBSTANCES ACTIVES
  申请人：ESTEVE LABOR DR

  公开号：WO2007090661A2

  公开（公告）日：2007-08-16

  [EN] The present invention relates to active substance combination comprising at least one derivative of aryl (or heteroaryl) azolylcarbinol compounds and at least one gabapentinoid, a medicament comprising said active substance combination, a pharmaceutical formulation comprising said active substance combination and the use of said active substance combination for the manufacture of a medicament.
  [FR] La présente invention concerne une combinaison de substances actives qui comprend au moins un dérivé de composés d'aryl (ou hétéroaryl) azolylcarbinol et au moins un gabapentinoïde. L'invention concerne également un médicament comprenant ladite combinaison de substances actives, une formulation pharmaceutique comprenant ladite combinaison de substances actives et l'utilisation de ladite combinaison de substances actives dans la fabrication d'un médicament.
• Investigation into the preferred conformation of gabapentin for interaction with its binding site on the α2δ subunit of a calcium channel
  作者：Justin S. Bryans、Natasha Davies、Nicolas S. Gee、David C. Horwell、Clare O. Kneen、Andrew I. Morrell、Jacqueline A. O'Neill、Giles S. Ratcliffe

  DOI：10.1016/s0960-894x(97)10002-6

  日期：1997.10

  A series of conformationally restricted Gabapentin analogues has been synthesised and used to propose the preferred conformation of Gabapentin for it to bind to the alpha(2) delta subunit of a calcium channel. (C) 1997 Elsevier Science Ltd.
• Oxadiazolone bioisosteres of pregabalin and gabapentin
  作者：David J. Wustrow、Thomas R. Belliotti、Thomas Capiris、Clare O. Kneen、Justin S. Bryans、Mark J. Field、Dic Williams、Ayman El-Kattan、Lisa Buchholz、Jack J. Kinsora、Susan M. Lotarski、Mark G. Vartanian、Charles P. Taylor、Sean D. Donevan、Andrew J. Thorpe、Jacob B. Schwarz

  DOI：10.1016/j.bmcl.2008.10.101

  日期：2009.1

  A series of oxadiazolone bioisosteres of pregabalin 1 and gabapentin 2 were prepared, and several were found to exhibit similar potency for the alpha(2)-delta subunit of voltage-gated calcium channels. Oxadiazolone 9 derived from 2 achieved low brain uptake but was nevertheless active in models of osteoarthritis. The high clearance associated with compound 9 was postulated to be a consequence of efflux by OAT and/or OCT, and was attenuated on co-administration with cimetidine or probenecid. (C) 2008 Published by Elsevier Ltd.