3-amino-6-methoxyisoindol-1-one

• 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: 3-amino-6-methoxyisoindol-1-one
• 英文别名: 3-Imino-6-methoxyisoindol-1-one；3-imino-6-methoxyisoindol-1-one
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: AYSYFLHEZBKBHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-amino-6-methoxyisoindol-1-one 生成 ethyl (2Z)-2-cyano-2-(5-methoxy-3-oxoisoindol-1-ylidene)acetate
  参考文献：
  名称：

  WROBEL, JAY E.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基-5-甲氧基苯甲酸甲酯 在 氨 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 3-amino-6-methoxyisoindol-1-one
  参考文献：
  名称：

  Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents

  摘要：

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.

  DOI：

  10.1021/jm00102a016

文献信息

• Dyestuffs from phthalimide derivatives
  申请人：ICI LTD

  公开号：US02537352A1

  公开（公告）日：1951-01-09
• WROBEL, JAY E.
  作者：WROBEL, JAY E.

  DOI：——

  日期：——
• Utilisation de dérivés de la Di-imino-isoindoline ou de la 3-amino-isoindolone pour la teinture des fibres kératiniques et compositions de teinture les renfermant
  申请人：L'OREAL

  公开号：EP0847749B1

  公开（公告）日：1999-12-01
• PROCEDE DE TEINTURE METTANT EN OEUVRE UN COMPOSE A METHYLENE ACTIF SPECIFIQUE ET UN COMPOSE CHOISI PARMI UN ALDEHYDE SPECIFIQUE, UNE CETONE SPECIFIQUE, UNE QUINONE ET UN DERIVE DE LA DI-IMINO-ISOINDOLINE OU DE LA 3-AMINO-ISOINDOLONE
  申请人：L'OREAL

  公开号：EP1056433B1

  公开（公告）日：2005-05-11
• PROCEDE DE TEINTURE DES CHEVEUX UTILISANT UNE AMINE CATIONIQUE HETEROCYCLIQUE ET UN ALDEHYDE OU CETONE OU QUINONE OU DERIVES DE LA DI-IMINO-ISOINDOLINE OU DE LA 3-AMINO-ISOINDOLONE
  申请人：L'ORÉAL

  公开号：EP1056435B9

  公开（公告）日：2007-01-10