4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-(3-((5,6-methylenedioxyindoline-1-yl) carbonyloxy)-2-phenylpropyl)piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-(3-((5,6-methylenedioxyindoline-1-yl) carbonyloxy)-2-phenylpropyl)piperidine
• 英文别名: 4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-(3-((5,6-methylenedioxyindolin-1-yl)carbonyloxy)-2-phenylpropyl)piperidine；[3-[4-(6-Fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]-2-phenylpropyl] 6,7-dihydro-[1,3]dioxolo[4,5-f]indole-5-carboxylate
• 化学式: C₃₁H₃₀FN₃O₅
• 分子量: 543.595
• InChiKey: PMUDAJIDIRHSBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-苯基丙烯酸 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 异丙醇 、 甲苯 为溶剂， 反应 3.33h， 生成 4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-(3-((5,6-methylenedioxyindoline-1-yl) carbonyloxy)-2-phenylpropyl)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

• PIPERIDINE DERIVATIVES, THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：EP0700396A1

  公开（公告）日：1996-03-13
• US5478845A
  申请人：——

  公开号：US5478845A

  公开（公告）日：1995-12-26
• [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：WO1994027994A1

  公开（公告）日：1994-12-08

  (EN) Piperidine derivatives of formula (I) wherein A is straight or branched alkyl, alkoxy-alkyl, or alkenyl; X is O or NH; Y is O, S, NH, NCN, or N-alkyl; R1 is 6-fluoro-1,2-benzisoxazol-3-yl, 6-fluoro-1H-indazol-3-yl, or 6-fluoro-1-methyl-1H-indazol-3-yl; R2 is alkyl or phenyl; and R3 is phenyl optionally substituted, or R3 is (a) wherein Z 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 de la formule (I) dans laquelle A représente alkyle, alkoxy-alkyle ou alkényle ramifié ou droit; X représente O ou NH; Y représente O, S, NH, NCN ou N-alkyle; R1 représente 6-fluoro-1,2-benzisoxazol-3-yle, 6-fluoro-1H-indazol-3-yle ou 6-fluoro-1-méthyle-1H-indazol-3-yle; R2 représente alkyle ou phényle; et R3 représente phényle optionnellement substitué, ou R3 représente (a) dans laquelle Z représente une chaîne fermée hétérocyclique à 5 ou 6 éléments; ou R2 et R3 forment ensemble avec l'atome d'azote un système d'anneaux hétérocycliques fusionnés. L'invention décrit également les sels pharmaceutiquement acceptables de ces dérivés. Ces dérivés et leurs sels sont utiles dans le traitement des symptômes concernant le système nerveux central, le système cardio-vasculaire ou 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.