4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-(5-hydroxy-3,3-pentamethylenepent-1-yl)piperidine | 161884-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: 4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-(5-hydroxy-3,3-pentamethylenepent-1-yl)piperidine
• 英文别名: 2-[1-[2-[4-(6-Fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]cyclohexyl]ethanol
• CAS: 161884-94-2
• 化学式: C₂₂H₃₁FN₂O₂
• 分子量: 374.499
• InChiKey: AGFDGRXPFNWACM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  49.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基异氰酸苯酯 、 4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-(5-hydroxy-3,3-pentamethylenepent-1-yl)piperidine 以23%的产率得到4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-[5-(3,4,5-trimethoxyphenyl-carbamoyloxy)-3,3-pentamethylenepent-1-yl]piperidine
  参考文献：
  名称：

  Mesolimbic selective antipsychotic arylcarbamates

  摘要：

  4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidine has been linked to various arylcarbamates to obtain compounds having affinity for dopamine-D-1 and -D-2, serotonin 5HT(2A) and alpha(1)-adrenoceptors. When Linkers with restricted flexibility are used, the biological activity is reduced indicating that a bended conformation is needed in this series of bioactive molecules. Compounds with a relatively low D-2/5HT(2A) affinity ratio in receptor binding experiments and high affinity for the alpha(1)-adrenoceptors exhibit a pharmacological profile which suggests a preferential effect on the mesocorticolimbic dopaminergic system and an 'atypical' antipsychotic activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80009-9
• 作为产物：
  描述：

  6-氟-3-哌啶-4-基-1,2-苯并异唑盐酸盐 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-(5-hydroxy-3,3-pentamethylenepent-1-yl)piperidine
  参考文献：
  名称：

  Mesolimbic selective antipsychotic arylcarbamates

  摘要：

  4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidine has been linked to various arylcarbamates to obtain compounds having affinity for dopamine-D-1 and -D-2, serotonin 5HT(2A) and alpha(1)-adrenoceptors. When Linkers with restricted flexibility are used, the biological activity is reduced indicating that a bended conformation is needed in this series of bioactive molecules. Compounds with a relatively low D-2/5HT(2A) affinity ratio in receptor binding experiments and high affinity for the alpha(1)-adrenoceptors exhibit a pharmacological profile which suggests a preferential effect on the mesocorticolimbic dopaminergic system and an 'atypical' antipsychotic activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80009-9

文献信息

• [EN] PIPERIDINE DERIVATIVES, THEIR PREPARATION AND USE<br/>[FR] DERIVES DE PIPERIDINE, LEUR PREPARATION ET LEUR UTILISATION
  申请人：NOVO NORDISK A/S

  公开号：WO1994027992A1

  公开（公告）日：1994-12-08

  (EN) Piperidine derivatives of formula (I) wherein n and m independently are 0, 1, 2, or 3; A is cycloalkylene or cycloalkylidenes; X is O or NH; Y is O, S, NH, NCN, or N-lower alkyl; R1 is 1,2-benzisoxazol-3-yl, 1H-indazol-3-yl, or 1-methyl-1H-indazol-3-yl, all of which may be substituted; R2 is H or alkyl; and R3 is phenyl optionally substituted, or R3 is (a) wherein Z together with the double bond in the phenyl ring represents a 5- or 6-membered heterocyclic ring; or R2 and R3 together with the nitrogen atom form a fused heterocyclic ring system; or pharmaceutically acceptable salts thereof are useful in the treatment of indications related to the CNS-system, cardiovascular system or to gastrointestinal disorders.(FR) L'invention concerne des dérivés de pipéridine selon la formule (I) dans laquelle n et m valent indépendamment 0, 1, 2 ou 3; A représente cycloalkylène ou cycloalkylidènes; X représente O ou NH; Y représente O, S, NH, NCN ou N-alkyle inférieur; R1 représente 1,2-benzisoxazol-3-yle, 1H-indazol-3-yle ou 1-méthyle-1H-indazol-3-yle, pouvant tous être substitués; R2 représente H ou alkyle; et R3 représente phényle optionnellement substitué, ou R3 représente (a) où Z, conjointement avec la double liaison dans la chaîne fermée phényle, représente une chaîne fermée hétérocyclique à 5 ou 6 éléments; ou R2 et R3, conjointement avec l'atome d'azote, forment un système de chaîne fermée hétérocyclique condensé. L'invention décrit également les sels pharmaceutiquement acceptables de ces dérivés. Ces dérivés et leurs sels sont utiles dans le traitement d'affections concernant le système nerveux central, le système cardio-vasculaire et les maladies gastro-intestinales.
• Mesolimbic selective antipsychotic arylcarbamates
  作者：John Bondo Hansen、Anders Fink-Jensen、Birgitte V. Christensen、Frederick C. Grønvald、Lone Jeppesen、John P. Mogensen、Erik B. Nielsen、Mark A. Scheideler、Francis J. White、Xu-Feng Zhang

  DOI：10.1016/s0223-5234(99)80009-9

  日期：1998.11

  4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidine has been linked to various arylcarbamates to obtain compounds having affinity for dopamine-D-1 and -D-2, serotonin 5HT(2A) and alpha(1)-adrenoceptors. When Linkers with restricted flexibility are used, the biological activity is reduced indicating that a bended conformation is needed in this series of bioactive molecules. Compounds with a relatively low D-2/5HT(2A) affinity ratio in receptor binding experiments and high affinity for the alpha(1)-adrenoceptors exhibit a pharmacological profile which suggests a preferential effect on the mesocorticolimbic dopaminergic system and an 'atypical' antipsychotic activity. (C) Elsevier, Paris.