1-(cyclohexylmethyl)piperidin-4-ol | 149398-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(cyclohexylmethyl)piperidin-4-ol
• CAS: 149398-34-5
• 化学式: C₁₂H₂₃NO
• mdl: MFCD13514838
• 分子量: 197.321
• InChiKey: KOPWAFHLXPKZFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(cyclohexylmethyl)piperidin-4-ol 、 Thioctic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 盐酸 作用下， 以 二氯甲烷 、 1,4-二氧六环 、 水 为溶剂， 反应 3.17h， 以39.6%的产率得到1-(cyclohexylmethyl)piperidin-4-yl 5(1,2-dithiolan-3-yl)pentanoate hydrochloride
  参考文献：
  名称：

  Design and Synthesis of New Bifunctional Sigma-1 Selective Ligands with Antioxidant Activity

  摘要：

  Herein we report the synthesis of new bifunctional sigma-1 (sigma(1))-selective ligands with antioxidant activity. To achieve this goal, we combined the structure of lipoic acid, a universal antioxidant, with an appropriate sigma aminic moiety. Ligands 14 and 26 displayed high affinity and selectivity for sigma(1) receptors (K-i sigma(1) = 1.8 and 5.5 nM; K-i sigma(2)/sigma(1) = 354 and 414, respectively). Compound 26 exhibited in vivo antiopioid effects on kappa opioid (KOP) receptor-mediated analgesia. In rat liver and brain mitochondria (RLM, RBM), this compound significantly reduced the swelling and the oxidation of thiol groups induced by calcium ions. Our results demonstrate that the tested compound has protective effects against oxidative stress.

  DOI：

  10.1021/jm3017893
• 作为产物：
  描述：

  4-羟基哌啶 、 溴甲基环己烷 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 1-(cyclohexylmethyl)piperidin-4-ol
  参考文献：
  名称：

  Design and Synthesis of New Bifunctional Sigma-1 Selective Ligands with Antioxidant Activity

  摘要：

  Herein we report the synthesis of new bifunctional sigma-1 (sigma(1))-selective ligands with antioxidant activity. To achieve this goal, we combined the structure of lipoic acid, a universal antioxidant, with an appropriate sigma aminic moiety. Ligands 14 and 26 displayed high affinity and selectivity for sigma(1) receptors (K-i sigma(1) = 1.8 and 5.5 nM; K-i sigma(2)/sigma(1) = 354 and 414, respectively). Compound 26 exhibited in vivo antiopioid effects on kappa opioid (KOP) receptor-mediated analgesia. In rat liver and brain mitochondria (RLM, RBM), this compound significantly reduced the swelling and the oxidation of thiol groups induced by calcium ions. Our results demonstrate that the tested compound has protective effects against oxidative stress.

  DOI：

  10.1021/jm3017893

文献信息

• [EN] NON-LYSOSOMAL GLUCOSYLCERAMIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE GLUCOSYLCÉRAMIDASES NON LYSOSOMALES ET LEURS UTILISATIONS
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2021224864A1

  公开（公告）日：2021-11-11

  The invention provides compounds for inhibiting glucosylceramidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds.

  该发明提供了用于抑制葡萄糖酰胺酶的化合物，这些化合物的前药，以及包括这些化合物或化合物的前药的药物组合物。
• [EN] 4-DIPHENYLACETOXY-N-SUBSTITUTED PIPERIDINES WITH ANTIMUSCARINIC ACTIVITY
  申请人：BRITISH TECHNOLOGY GROUP LTD.

  公开号：WO1993007122A1

  公开（公告）日：1993-04-15

  (EN) Compounds of formula (I) in which R1 and R2 are each separately selected from a phenyl group which is unsubstituted or substituted by one or more groups selected from alkyl, alkoxy, alkylenedioxy, halogeno, halogeno substituted alkyl, hydroxy and nitro, R3 and R4 are each hydrogen or together are an oxo group and R5 is an alicyclic hydrocarbyl group containing from 3 to 9 carbon atoms in the ring, the compound optionally being in the form of a physiologically acceptable acid addition or quaternary ammonium salt, are of value as selective antagonists of the M3 muscarinic receptor.(FR) Composés de la formule (I) dans laquelle R1 et R2 sont séparément choisis à partir d'un groupe phényle non substitué ou substitué par un ou plusieurs groupes choisis entre alkyle, alcoxy, alkylènedioxy, halogéno, alkyle substitué par halogéno, hydroxy et nitro, R3 et R4 représentent chacun hydrogène ou représentent ensemble un groupe oxo, et R5 représente un groupe hydrocarbyle alicyclique contenant entre 3 et 9 atomes de carbone dans le cycle, le composé se présentant éventuellement sous la forme d'un sel d'addition acide ou d'un sel d'ammonium quaternaire physiologiquement acceptables. Ces composés peuvent être utilisés comme antagonistes sélectifs du récepteur muscarinique M3.
• Design and Synthesis of New Bifunctional Sigma-1 Selective Ligands with Antioxidant Activity
  作者：O. Prezzavento、E. Arena、C. Parenti、L. Pasquinucci、G. Aricò、G. M. Scoto、S. Grancara、A. Toninello、S. Ronsisvalle

  DOI：10.1021/jm3017893

  日期：2013.3.28

  Herein we report the synthesis of new bifunctional sigma-1 (sigma(1))-selective ligands with antioxidant activity. To achieve this goal, we combined the structure of lipoic acid, a universal antioxidant, with an appropriate sigma aminic moiety. Ligands 14 and 26 displayed high affinity and selectivity for sigma(1) receptors (K-i sigma(1) = 1.8 and 5.5 nM; K-i sigma(2)/sigma(1) = 354 and 414, respectively). Compound 26 exhibited in vivo antiopioid effects on kappa opioid (KOP) receptor-mediated analgesia. In rat liver and brain mitochondria (RLM, RBM), this compound significantly reduced the swelling and the oxidation of thiol groups induced by calcium ions. Our results demonstrate that the tested compound has protective effects against oxidative stress.