2-苄基-3-氧代-1H-异吲哚-4-羧酸 | 77960-29-3

• 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: 2-苄基-3-氧代-1H-异吲哚-4-羧酸
• 英文名称: 2-benzyl-3-oxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
• 英文别名: 2-benzyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid；2-benzyl-3-oxoisoindoline-4-carboxylic acid；2-benzyl-7-carboxyisoindolin-1-one；2-benzyl-3-oxo-1H-isoindole-4-carboxylic acid
• CAS: 77960-29-3
• 化学式: C₁₆H₁₃NO₃
• mdl: MFCD02766482
• 分子量: 267.284
• InChiKey: FFIYKQCBUSMRHR-UHFFFAOYSA-N

物化性质

• 熔点：
  177-178.5 °C(Solv: isopropanol (67-63-0); N,N-dimethylformamide (68-12-2))
• 沸点：
  530.3±50.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)
• 溶解度：
  >40.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  2-苄基-3-氧代-1H-异吲哚-4-羧酸 在 lithium aluminium tetrahydride 、 cesium fluoride 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 N-benzyl-N-(1,3-dihydro-2-benzofuran-4-ylmethyl)aniline
  参考文献：
  名称：

  The interaction of 4-hydroxymethyl isoindolines with dehydrobenzene. Synthesis of 3-phenylaminomethyldihydrobenzo[c]furanes

  摘要：

  2-Alkyl or 2-aryl-substituted 4-hydroxymethylisoindolines smoothly undergo intramolecular recyclization through reaction with arynes to give isobenzofurans with good yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.01.022
• 作为产物：
  描述：

  2-benzyl-1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic acid 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以78%的产率得到2-苄基-3-氧代-1H-异吲哚-4-羧酸
  参考文献：
  名称：

  Virtual Screening and Computational Optimization for the Discovery of Covalent Prolyl Oligopeptidase Inhibitors with Activity in Human Cells

  摘要：

  Our docking program, Fitted, implemented in our computational platform, Forecaster, has been modified to carry out automated virtual screening of covalent inhibitors. With this modified version of the program, virtual screening and further docking-based optimization of a selected hit led to the identification of potential covalent reversible inhibitors of prolyl oligopeptidase activity. After visual inspection, a virtual hit molecule together with four analogues were selected for synthesis and made in one five chemical steps. Biological evaluations on recombinant POP and FAP alpha enzymes, cell extracts, and living cells demonstrated high potency and selectivity for POP over FAP alpha and DPPIV. Three compounds even exhibited high nanomolar inhibitory activities in intact living human cells and acceptable metabolic stability. This small set of molecules also demonstrated that covalent binding and/or geometrical constraints to the ligand/protein complex may lead to an increase in bioactivity.

  DOI：

  10.1021/jm3002839

文献信息

• New class of hantaan virus inhibitors based on conjugation of the isoindole fragment to (+)-camphor or (−)-fenchone hydrazonesv
  作者：Olga I. Yarovaya、Kseniya S. Kovaleva、Anna A. Zaykovskaya、Liudmila N. Yashina、Nadezda S. Scherbakova、Dmitry N. Scherbakov、Sophia S. Borisevich、Fedor I. Zubkov、Alexandra S. Antonova、Roman Yu. Peshkov、Ilia V. Eltsov、Oleg V. Pyankov、Rinat A. Maksyutov、Nariman F. Salakhutdinov

  DOI：10.1016/j.bmcl.2021.127926

  日期：2021.5

  This work presents the design and synthesis of camphor, fenchone, and norcamphor N-acylhydrazone derivatives as a new class of inhibitors of the Hantaan virus, which causes haemorrhagic fever with renal syndrome (HFRS). A cytopathic model was developed for testing chemotherapeutics against the Hantaan virus, strain 76–118. In addition, a study of the antiviral activity was carried out using a pseudoviral

  这项工作介绍了樟脑、茴香酮和去甲樟脑N-酰基腙衍生物的设计和合成，作为汉坦病毒的一类新抑制剂，汉坦病毒会导致肾综合征出血热 (HFRS)。开发了一种细胞病变模型，用于测试针对汉坦病毒 76-118 毒株的化疗药物。此外，使用假病毒系统进行了抗病毒活性的研究。发现命中化合物具有显着的活性 (IC 50  = 7.6 ± 2 µM) 以及低毒性 (CC 50  > 1000 µM)。使用分子对接程序，评估与汉坦病毒核蛋白的结合，并建立合成化合物的结构与抗病毒活性之间的相关性。
• [EN] ISOINDOLINE-1-ONE DERIVATIVES AS CHOLINERGIC MUSCARINIC M1 RECEPTOR POSITIVE ALLOESTERIC MODULATOR ACTIVITY FOR THE TREATMENT OF ALZHEIMERS DISEASE<br/>[FR] DÉRIVÉS I ISOINDOLINE-1-ONE À ACTIVITÉ DE MODULATEUR ALLOESTÉRIQUE POSITIF DU RÉCEPTEUR M1 MUSCARINIQUE CHOLINERGIQUE POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2015163485A1

  公开（公告）日：2015-10-29

  The present invention provides a compound having a cholinergic muscarinic M1 receptor positive allosteric modulator activity and useful as an agent for the prophylaxis or treatment of Alzheimer's disease, schizophrenia, pain, sleep disorder, Parkinson's disease dementia, dementia with Lewy bodies, and the like. The present invention relates to a compound represented by the formula (I) or a salt thereof. (I) wherein each symbol is as described in the specification, or a salt thereof.

  本发明提供了一种具有胆碱能M1受体阳性变构调节剂活性的化合物，可用作预防或治疗阿尔茨海默病、精神分裂症、疼痛、睡眠障碍、帕金森病痴呆、带有Lewy小体的痴呆等疾病的药物。本发明涉及由式(I)表示的化合物或其盐。其中，每个符号如规范中所述，或其盐。
• A facile, protic ionic liquid route to N-substituted 5-hydroxy-4-methyl-3-oxoisoindoline-1-carboxamides and N-substituted 3-oxoisoindoline-4-carboxylic acids
  作者：Christopher P Gordon、Nolene Byrne、Adam McCluskey

  DOI：10.1039/b924835h

  日期：——

  Treatment of highly decorated bicyclo[2.2.1]heptadienes with the protic ionic liquid, TfOH:TEA effected quantitative conversion to the corresponding N-substituted 5-hydroxy-4-methyl-3-oxoisoindoline-1-carboxamides. This approach provides rapid access important chemical space for the rapid development of highly functionalised oxoisoindoline and is highly substrate tolerant.

  用质子离子液体处理高度修饰的双环[2.2.1]庚二烯， 三氟乙酸：茶 实现了定量转换为相应的 ñ-取代的5-羟基-4-甲基-3-氧代异吲哚啉-1-羧酰胺。这种方法为快速开发高度功能化的产品提供了重要的化学空间氧代异吲哚啉 并且对底物的耐受性很高。
• Synthesis of Advanced Intermediates of Lennoxamine Analogues
  作者：Girish Trivedi、Manikrao Salunkhe、Prajakta Sarang、Arun Yadav、Prashant Patil、Urlam Krishna

  DOI：10.1055/s-2007-965950

  日期：2007.4

  A simple and convenient method for synthesis of advanced isoindolone intermediates of lennoxamine and analogues is described in this paper. The intramolecular Diels-Alder reaction of furan is used as a key step in this synthesis.

  本文介绍了一种简单易行的方法，用于合成高级异吲哚酮中间体伦诺沙明及其类似物。呋喃的分子内 Diels-Alder 反应是该合成的关键步骤。
• Cycloaddition of furfurylamines to maleic anhydride and its substituted derivatives
  作者：V. P. Zaytsev、N. M. Mikhailova、I. K. Airiyan、E. V. Galkina、V. D. Golubev、E. V. Nikitina、F. I. Zubkov、A. V. Varlamov

  DOI：10.1007/s10593-012-1023-1

  日期：2012.6

  The regio- and stereoselectivity of the [4 + 2] cycloaddition of maleic, citraconic, dichloromaleic, and dibromomaleic anhydrides to difurfuryl amines and secondary furfurylamines were studied. N-Furfuryl-, N-phenyl-, and N-benzylhexahydrooxoepoxyisoindole-7-carboxylic acids were synthesized. An approach was developed for obtaining hexahydroepoxyoxoisoindole-7-carboxylic acid unsubstituted at the nitrogen

  研究了马来酸酐，柠康酸酐，二氯马来酸酐和二溴马来酸酐与[4 + 2]环加成反应对二糠胺和仲糠胺的区域和立体选择性。Ñ -Furfuryl-，Ñ苯基，和Ñ -benzylhexahydrooxoepoxyisoindole -7-羧酸合成的。开发了一种获得在氮原子上未取代的六氢环氧氧代异吲哚-7-羧酸的方法。二卤代环氧异吲哚酮羧酸的氧杂环庚烯片段的芳构化得到一系列的7-羧基-2-R-异吲哚-1-酮。