5-phenylisoindoline

• 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: 5-phenylisoindoline
• 英文别名: 5-phenyl-2,3-dihydro-1H-isoindole
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: SKFGGYSYEHRZCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-phenylisoindoline 、 (S)-2-(1-甲基-2,2,2-三氟乙氧基)-5-甲基磺酰基苯甲酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-(5-phenyl-1,3-dihydro-isoindol-2-yl)-methanone
  参考文献：
  名称：

  Discovery of benzoylisoindolines as a novel class of potent, selective and orally active GlyT1 inhibitors

  摘要：

  Benzoylisoindolines were discovered as a novel structural class of GlyT1 inhibitors. SAR studies and subsequent lead optimization efforts focused primarily on addressing hERG liability and on improving in vivo efficacy resulted in the identification of potent GlyT1 inhibitors displaying excellent selectivity and in vivo PD and PK profiles. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.124
• 作为产物：
  描述：

  5-phenyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-phenylisoindoline
  参考文献：
  名称：

  Discovery of benzoylisoindolines as a novel class of potent, selective and orally active GlyT1 inhibitors

  摘要：

  Benzoylisoindolines were discovered as a novel structural class of GlyT1 inhibitors. SAR studies and subsequent lead optimization efforts focused primarily on addressing hERG liability and on improving in vivo efficacy resulted in the identification of potent GlyT1 inhibitors displaying excellent selectivity and in vivo PD and PK profiles. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.124

文献信息

• ABHD6 AND DUAL ABHD6/MGL INHIBITORS AND THEIR USES
  申请人：Malamas Michael

  公开号：US20190152917A1

  公开（公告）日：2019-05-23

  Provided herein are compounds and pharmaceutical compositions for selectively inhibiting serine hydrolase a/b-hydrolase domain 6 (ABHD6) and dually inhibiting ABHD6 and monoacylglycerol lipase (MGL). The compounds and pharmaceutical compositions disclosed herein are useful for treating a number of therapeutic conditions related to cannabinergic receptor function such as pain, inflammation, neuropathy, neurodegenerative diseases, anxiety disorders, motor function disorder, metabolic disorder, glaucoma and chemotherapy-induced nausea and vomiting and cancer.

  本文提供了一些化合物和药物组合物，用于选择性抑制丝氨酸水解酶a/b-水解酶结构域6（ABHD6），以及双重抑制ABHD6和单酰基甘油脂酶（MGL）。本文披露的化合物和药物组合物对治疗与大麻受体功能相关的多种治疗条件具有用处，如疼痛、炎症、神经病变、神经退行性疾病、焦虑症、运动功能障碍、代谢紊乱、青光眼、化疗引起的恶心和呕吐以及癌症。
• ABHD6 and dual ABHD6/MGL inhibitors and their uses
  申请人：MAKScientific, LLC

  公开号：US10662159B2

  公开（公告）日：2020-05-26

  Provided herein are compounds and pharmaceutical compositions for selectively inhibiting serine hydrolase a/b-hydrolase domain 6 (ABHD6) and dually inhibiting ABHD6 and monoacylglycerol lipase (MGL). The compounds and pharmaceutical compositions disclosed herein are useful for treating a number of therapeutic conditions related to cannabinergic receptor function such as pain, inflammation, neuropathy, neurodegenerative diseases, anxiety disorders, motor function disorder, metabolic disorder, glaucoma and chemotherapy-induced nausea and vomiting and cancer.

  本文提供了选择性抑制丝氨酸水解酶 a/b-hydrolase domain 6 (ABHD6)和双重抑制 ABHD6 和单酰基甘油脂肪酶 (MGL) 的化合物和药物组合物。本文公开的化合物和药物组合物可用于治疗多种与大麻素能受体功能相关的治疗性疾病，如疼痛、炎症、神经病变、神经退行性疾病、焦虑症、运动功能障碍、代谢紊乱、青光眼、化疗引起的恶心和呕吐以及癌症。
• Cyanopyrrolidines as dub inhibitors for the treatment of cancer
  申请人：MISSION THERAPEUTICS LIMITED

  公开号：US10669234B2

  公开（公告）日：2020-06-02

  The present invention relates to novel compounds and method for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase L1 (UCHL1) and ubiquitin C-terminal hydrolase 30 or ubiquitin specific peptidase 30 (USP30). The invention further relates to the use of DUB inhibitors in the treatment of cancer and conditions involving mitochondrial dysfunction. Compounds of the invention include compounds having the formula (I) or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 are as defined herein.

  本发明涉及新型化合物和去泛素化酶（DUB）抑制剂的制造方法。特别是，本发明涉及对泛素 C 端水解酶 L1（UCHL1）和泛素 C 端水解酶 30 或泛素特异性肽酶 30（USP30）的抑制。本发明进一步涉及 DUB 抑制剂在治疗癌症和涉及线粒体功能障碍的疾病中的用途。本发明的化合物包括具有式(I)的化合物或其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8和R9如本文所定义。
• Microwave-assisted iridium-catalyzed [2+2+2] cycloaddition of resin-bound dipropargylamine with alkynes
  作者：Muthian Shanmugasundaram、Ana Luisa Aguirre、Melissa Leyva、Beili Quan、Luis E. Martinez

  DOI：10.1016/j.tetlet.2007.08.073

  日期：2007.10

  The [Ir(COD)Cl](2)/dppe system effectively catalyzes the solid-phase [2+2+2] cycloaddition of resin-bound dipropargylamine with alkynes under microwave conditions. The reaction results in high purity of isoindoline derivatives with moderate yields. (C) 2007 Elsevier Ltd. All rights reserved.
• CYANOPYRROLIDINES AS DUB INHIBITORS FOR THE TREATMENT OF CANCER
  申请人：Mission Therapeutics Limited

  公开号：EP3322702B1

  公开（公告）日：2019-11-20