2-[2-(4-benzyloxyphenyl)ethyl]-5-methoxy-4-pentyloxy-2,3-dihydroisoindol-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: 2-[2-(4-benzyloxyphenyl)ethyl]-5-methoxy-4-pentyloxy-2,3-dihydroisoindol-1-one
• 英文别名: 5-methoxy-4-pentoxy-2-[2-(4-phenylmethoxyphenyl)ethyl]-3H-isoindol-1-one
• 化学式: C₂₉H₃₃NO₄
• 分子量: 459.585
• InChiKey: YXPGUQPWTPNNRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(4-benzyloxyphenyl)ethyl]-5-methoxy-4-pentyloxy-2,3-dihydroisoindol-1-one 在 palladium-carbon catalyst 作用下， 以 水 、 氢气 、 乙酸乙酯 为溶剂， 以74.1%的产率得到2-[2-(4-hydroxyphenyl)ethyl]-5-methoxy-4-pentyloxy-2,3-dihydroisoindol-1-one
  参考文献：
  名称：

  Compounds and pharmaceutical use thereof

  摘要：

  公式（I）##STR1##中的化合物，其中每个符号如说明书中所定义，其药用可接受的盐及其医药用途。本发明的化合物（I）及其药用可接受的盐对大麻素受体具有选择性作用，尤其是外周受体，对中枢系统的副作用较小，并且具有卓越的免疫调节作用、抗炎作用、抗过敏作用和对肾炎的治疗效果。因此，它们作为大麻素受体，尤其是外周大麻素受体的激动剂和拮抗剂，免疫调节剂，自身免疫性疾病的治疗剂，抗炎剂，抗过敏剂和肾炎的治疗剂是有用的。

  公开号：

  US06017919A1
• 作为产物：
  描述：

  2-[2-(4-benzyloxyphenyl)ethyl]-3-hydroxy-5-methoxy-4-pentyloxy-2,3-dihydroisoindol-1-one 、 碳酸氢钠 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以99.8%的产率得到2-[2-(4-benzyloxyphenyl)ethyl]-5-methoxy-4-pentyloxy-2,3-dihydroisoindol-1-one
  参考文献：
  名称：

  Compounds and pharmaceutical use thereof

  摘要：

  公式（I）##STR1##中的化合物，其中每个符号如说明书中所定义，其药用可接受的盐及其医药用途。本发明的化合物（I）及其药用可接受的盐对大麻素受体具有选择性作用，尤其是外周受体，对中枢系统的副作用较小，并且具有卓越的免疫调节作用、抗炎作用、抗过敏作用和对肾炎的治疗效果。因此，它们作为大麻素受体，尤其是外周大麻素受体的激动剂和拮抗剂，免疫调节剂，自身免疫性疾病的治疗剂，抗炎剂，抗过敏剂和肾炎的治疗剂是有用的。

  公开号：

  US06017919A1

文献信息

• Antipruritics
  申请人：Yasui Kiyoshi

  公开号：US20050101590A1

  公开（公告）日：2005-05-12

  It is intended to provide antipruritics (drugs to control itching, antiitch agents and drugs to stop itching). It is found out that a compound having an agonistic activity to the cannabinoid receptor shows an antipruritics effect.

  这意味着它旨在提供止痒药（用于控制瘙痒的药物，抗瘙痒剂和止痒药）。研究发现，具有激动性作用的大麻素受体的化合物具有止痒效果。
• NOVEL COMPOUNDS AND PHARMACEUTICAL USE THEREOF
  申请人：Japan Tobacco Inc.

  公开号：EP0887340A1

  公开（公告）日：1998-12-30

  The compounds of the formula (I) wherein each symbol is as defined in the specification, pharmaceutically acceptable salts thereof and pharmaceutical use thereof. The Compound (I) and pharmaceutically acceptable salts thereof of the present invention selectively act on cannabinoid receptors, particularly peripheral receptors, cause less side effects on the central system, and have superior immunoregulating action, antiinflammatory action, antiallergic action and therapeutic effect on nephritis. Therefore, they are useful as cannabinoid receptor, particularly peripheral cannabinoid receptor activators and antagonists, immunoregulators, therapeutic agents for autoimmune diseases, antiinflammatory agents, antiallergic agents and therapeutic agents for nephritis.

  式 (I) 的化合物 其中各符号如说明书中所定义，其药学上可接受的盐及其制药用途。本发明的化合物(I)及其药学上可接受的盐选择性地作用于大麻素受体，特别是外周受体，对中枢系统的副作用较小，具有优越的免疫调节作用、抗炎作用、抗过敏作用和对肾炎的治疗作用。因此，它们可用作大麻素受体（特别是外周大麻素受体）激活剂和拮抗剂、免疫调节剂、自身免疫性疾病治疗剂、抗炎剂、抗过敏剂和肾炎治疗剂。
• Protection of neurons against glutamate-induced damage in glaucoma and other conditions
  申请人：——

  公开号：US20020077322A1

  公开（公告）日：2002-06-20

  The present invention is directed to a method of protecting cells of the nervous system from glutamate-induced cytotoxicity , such as the type that is mimicked by administration of N-methyl-D-aspartate (NMDA), and which is associated with conditions such as ischemia or glaucoma. In general, the method comprises increasing the activity of a cannabinoid agonist that binds specifically to an endogenous cannabinoid receptor, such as the endogenous cannabinoid receptors CB 1 or CB 2 , to protect the cells against glutamate-induced neurotoxicity. This can be done either by the administration of a cannabinoid agonist such as a physiologically acceptable salt of R(+)-[2,3-dihydro-5-methyl3-[(morpholinyl)methyl]pyrrolo [1,2,3-de]-1,4-benzoxazinyl]-( 1 -naphthalenyl) methanone, preferably the mesylate salt, or by blocking degradation of naturally-occurring endogenous cannabinoid agonists in the cells, such as by inhibition of anandamide amidohydrolase. Administration can be performed by one of several routes, such as enterally, transdermally, or transmucosally.

  本发明涉及一种保护神经系统细胞免受谷氨酸诱导的细胞毒性的方法，例如通过施用 N-甲基-D-天冬氨酸（NMDA）模拟的细胞毒性，这种细胞毒性与缺血或青光眼等病症有关。一般来说，该方法包括提高与内源性大麻素受体（如内源性大麻素受体 CB 1 或 CB 2 等内源性大麻素受体结合的大麻素激动剂的活性，以保护细胞免受谷氨酸诱导的神经毒性的影响。这可以通过施用大麻素激动剂来实现，例如 R(+)-[2,3-二氢-5-甲基-3-[（吗啉基）甲基]吡咯[1,2,3-脱]-1,4-苯并恶嗪基]-(+)的生理上可接受的盐。 1 -萘基）甲酮，最好是甲磺酸盐，或通过阻断细胞中天然存在的内源性大麻素激动剂的降解，例如通过抑制安乃近酰胺酰胺水解酶。给药可通过多种途径之一进行，如肠内、经皮或经口。
• US6017919A
  申请人：——

  公开号：US6017919A

  公开（公告）日：2000-01-25
• [EN] PROTECTION OF NEURONS AGAINST GLUTAMATE-INDUCED DAMAGE IN GLAUCOMA AND OTHER CONDITIONS<br/>[FR] PROTECTION DES NEURONES CONTRE DES LESIONS INDUITES PAR LE GLUTAMATE POUR LE GLAUCOME ET D'AUTRES PATHOLOGIES
  申请人：AYOUB GEORGE S

  公开号：WO2002047691A1

  公开（公告）日：2002-06-20

  The present invention is directed to a method of protecting cells of the nervous system from glutamate-induced cytotoxicity, such as the type that is mimicked by administration of N-methyl-D-aspartate (NMDA), and which is associated with conditions such as ischemia or glaucoma. In general, the method comprises increasing the activity of a cannabinoid agonist that binds specifically to an endogenous cannabinoid receptor, such as the endogenous cannabinoid receptors CB1 or CB2, to protect the cells against glutamate-induced neurotoxicity. This can be done either by the administration of a cannabinoid agonist such as a physiologically acceptable salt of R(+)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo[1,2,3-de]-1,4-benzoxazinyl]-(1-naphthalenyl)methanone, preferably the mesylate salt, or by blocking degradation of naturally-occurring endogenous cannabinoid agonists in the cells, such as by inhibition of anandamide amidohydrolase. Administration can be performed by one of several routes, such as enterally, transdermally, or transmucosally.