1H-吲哚-3-乙酸,5-氯-2-甲基-1-(三甲基甲硅烷基)-,三甲基甲硅烷基酯 | 126091-37-0

• 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
• 中文名称: 1H-吲哚-3-乙酸,5-氯-2-甲基-1-(三甲基甲硅烷基)-,三甲基甲硅烷基酯
• 英文名称: (±)-3-isopropyl-2,3-dihydro-1H-isoindol-1-one
• 英文别名: 3-isopropylisoindolin-1-one；3-propan-2-yl-2,3-dihydroisoindol-1-one
• CAS: 126091-37-0
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: PGUXFHVBRYSFMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1H-吲哚-3-乙酸,5-氯-2-甲基-1-(三甲基甲硅烷基)-,三甲基甲硅烷基酯
  参考文献：
  名称：

  Discovery of 3-n-butyl-2,3-dihydro-1H-isoindol-1-one as a potential anti-ischemic stroke agent

  摘要：

  To develop novel anti-ischemic stroke agents with better therapeutic efficacy and bioavailability, we designed and synthesized a series of 3-alkyl-2,3-dihydro-1H-isoindol-1-ones compounds (3a-i) derivatives, one of which (3d) exhibited the strongest inhibitory activity for the adenosine diphosphate-induced and arachidonic acid-induced platelet aggregation. This activity is superior to that of 3-n-butylphthalide and comparable with aspirin and edaravone. Meanwhile, 3d not only exhibited a potent activity in scavenging free radicals and improving the survival of HT22 cells against the reactive oxygen species-mediated cytotoxicity in vitro but also significantly attenuated the ischemia/reperfusion-induced oxidative stress in ischemic rat brains. Results from transient middle cerebral artery occlusion and permanent middle cerebral artery occlusion model, indicated that 3d could significantly reduce infarct size, improve neurobehavioral deficits, and prominently decrease attenuation of cerebral damage. Most importantly, 3d possessed a very high absolute bioavailability and was rapidly distributed in brain tissue to keep high plasma drug concentration for the treatment of ischemic strokes. In conclusion, our findings suggest that 3-alkyl-2,3-dihydro-1H-isoindol-1-ones, a novel series of compounds, might be candidate drugs for the treatment of acute ischemic strokes, and 3d may be a promising therapeutic agent for the primary and secondary prevention of ischemic stroke.

  DOI：

  10.2147/dddt.s84731

文献信息

• Visible light-induced N-radical <i>5-exo</i>/<i>6-endo</i> cyclization of alkenyl amides: facile access to isoindolinones/isoquinolinones
  作者：Zhen-Yao Lei、Kui Hu、Yuan-Xiang He、Shu Geng、Li-Na Chen、Shuai Zou、Li Pan、Zhi-Jun Ding、Feng Huang

  DOI：10.1039/d2ob00317a

  日期：——

  An efficient N-centered radical intramolecular cyclization reaction of alkenyl amides induced by visible light was described. In this process, an alkenyl amide underwent 5-exo/6-endo cyclization to selectively yield two critical alkaloid structures, namely isoindolinones and isoquinolinones.

  描述了由可见光诱导的烯基酰胺的有效N中心自由基分子内环化反应。在这个过程中，烯基酰胺经历了5-exo / 6-endo环化以选择性地产生两种关键的生物碱结构，即异吲哚啉酮和异喹啉酮。
• Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones
  作者：Mu-Wang Chen、Qing-An Chen、Ying Duan、Zhi-Shi Ye、Yong-Gui Zhou

  DOI：10.1039/c2cc16832d

  日期：——

  Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones, was developed using chiral phosphoric acid as catalyst and a Hantzsch ester as the hydrogen source with up to 95% ee. The reaction process of this asymmetric transfer hydrogenation may occur directly through the acyliminium ion intermediate.

  使用手性磷酸作为催化剂和 Hantzsch 酯作为氢源开发了外消旋叔醇（3-取代的 3-羟基异吲哚啉-1-酮）的不对称氢解，其 ee 高达 95%。这种不对称转移氢化的反应过程可以直接通过酰亚胺离子中间体发生。
• SPIROCYCLOHEPTANES AS INHIBITORS OF ROCK
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160016914A1

  公开（公告）日：2016-01-21

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically-acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供式（I）的化合物：或其立体异构体，互变异构体或药学上可接受的盐，其中所有变量如本文所定义。这些化合物是选择性ROCK抑制剂。本发明还涉及包含这些化合物的制药组合物以及使用它们治疗心血管，平滑肌，肿瘤，神经病理，自身免疫，纤维化和/或炎症性疾病的方法。
• Opsin-binding ligands, compositions and methods of use
  申请人：Garvey David S.

  公开号：US20110003784A1

  公开（公告）日：2011-01-06

  Compounds and compositions of said compounds along with methods of use of compounds are disclosed for treating ophthalmic conditions related to mislocalization of opsin proteins, the misfolding of mutant opsin proteins and the production of toxic visual cycle products that accumulate in the eye. Compounds and compositions useful in the these methods, either alone or in combination with other therapeutic agents, are also described.

  本文披露了用于治疗与视蛋白蛋白质错位、突变视蛋白蛋白质的错折和在眼中积累有毒视觉循环产物相关的眼科疾病的化合物和该化合物的组合物以及使用该化合物的方法。本文还描述了用于这些方法的化合物和组合物，可以单独使用或与其他治疗药物联合使用。
• Lactam, cyclic urea and carbamate, and triazolone derivatives as potent and selective rock inhibitors
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US10730858B2

  公开（公告）日：2020-08-04

  The present invention provides compounds of Formula (I): Formula (I) or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供了式 (I) 的化合物：式（I）或其立体异构体、同系物或药学上可接受的盐，其中所有变量如本文所定义。这些化合物是选择性 ROCK 抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用这些化合物治疗心血管、平滑肌、肿瘤、神经病理、自身免疫、纤维化和/或炎症性疾病的方法。