2-(1-methylpyrrolidin-3-yloxy)isoindoline-1,3-dione | 160229-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(1-methylpyrrolidin-3-yloxy)isoindoline-1,3-dione
• 英文别名: 2-(1-Methylpyrrolidin-3-yl)oxyisoindole-1,3-dione
• CAS: 160229-79-8
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: UAJNEIONHNRCRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-methylpyrrolidin-3-yloxy)isoindoline-1,3-dione 在 盐酸 、 sodium carbonate 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 6.0h， 生成 3-(trifluoromethyl)benzaldehyde O-(1-methylpyrrolidin-3-yl) oxime
  参考文献：
  名称：

  Synthesis and evaluation of oxime derivatives as modulators for amyloid beta-induced mitochondrial dysfunction

  摘要：

  Starting from quinuclidinyl oxime 1 identified by preliminary screening, a series of azacycles-containing oxime derivatives was synthesized. Their mPTP blocking activities were evaluated by a JC-1 assay, measuring the change of mitochondrial membrane potential. The inhibitory activity of nine compounds against amyloid beta-induced mPTP opening was comparable or even superior to that of piracetam. Among them, 12d effectively maintained mitochondrial function and cell viabilities on the ATP assay, the MTT assay, and the ROS assay. In addition, it exhibited favorable in vitro stability and pharmacokinetic characteristics, which hold a promise for further development of AD therapeutics. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.033
• 作为产物：
  描述：

  3-羟基-1-甲基四氢吡咯 、 N-羟基邻苯二甲酰亚胺 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以97%的产率得到2-(1-methylpyrrolidin-3-yloxy)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and evaluation of oxime derivatives as modulators for amyloid beta-induced mitochondrial dysfunction

  摘要：

  Starting from quinuclidinyl oxime 1 identified by preliminary screening, a series of azacycles-containing oxime derivatives was synthesized. Their mPTP blocking activities were evaluated by a JC-1 assay, measuring the change of mitochondrial membrane potential. The inhibitory activity of nine compounds against amyloid beta-induced mPTP opening was comparable or even superior to that of piracetam. Among them, 12d effectively maintained mitochondrial function and cell viabilities on the ATP assay, the MTT assay, and the ROS assay. In addition, it exhibited favorable in vitro stability and pharmacokinetic characteristics, which hold a promise for further development of AD therapeutics. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.033

文献信息

• [EN] AZACYCLIC AND AZABICYCLIC HYDROXYLAMINES AS MUSCARINIC RECEPTOR AGONISTS<br/>[FR] ALKYLIDENE HYDROXYLAMINES AZACYCLIQUES ET AZABICYLIQUES UTILES COMME AGONISTES DES RECEPTEURS A LA MUSCARINE
  申请人：BOEHRINGER INGELHEIM ITALIA S.P.A.

  公开号：WO1994000448A1

  公开（公告）日：1994-01-06

  (EN) Pharmacologically active azacyclic and azabicyclic alkyliden hydroxylamines as cholinergic agents, useful in the treatment of neurological and mental diseases of formula (I), wherein A, n, R1 and R2 have the meanings specified in the description, a process for their preparation and pharmaceutical compositions containing them, are disclosed.(FR) L'invention concerne des alkylidène hydroxylamines azacycliques et azabicyliques de formule (I), utiles comme agents cholinergiques pour le traitement de troubles neurologiques et mentaux. Dans ladite formule, A, n, R1, et R2 ont la signification spécifiée dans la description. On décrit également un procédé de préparation de ces composés et des compositions pharmaceutiques les contenant.
• Synthesis and evaluation of oxime derivatives as modulators for amyloid beta-induced mitochondrial dysfunction
  作者：Young Seub Kim、Sun hwa Jung、Beoung-Geon Park、Min Kyung Ko、Hyun-Seo Jang、Kihang Choi、Ja-Hyun Baik、Jiyoun Lee、Jae Kyun Lee、Ae Nim Pae、Yong Seo Cho、Sun-Joon Min

  DOI：10.1016/j.ejmech.2012.12.033

  日期：2013.4

  Starting from quinuclidinyl oxime 1 identified by preliminary screening, a series of azacycles-containing oxime derivatives was synthesized. Their mPTP blocking activities were evaluated by a JC-1 assay, measuring the change of mitochondrial membrane potential. The inhibitory activity of nine compounds against amyloid beta-induced mPTP opening was comparable or even superior to that of piracetam. Among them, 12d effectively maintained mitochondrial function and cell viabilities on the ATP assay, the MTT assay, and the ROS assay. In addition, it exhibited favorable in vitro stability and pharmacokinetic characteristics, which hold a promise for further development of AD therapeutics. (C) 2012 Elsevier Masson SAS. All rights reserved.