1-(naphthalen-1-ylmethyl)indoline-2,3-dione | 79183-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(naphthalen-1-ylmethyl)indoline-2,3-dione
• 英文别名: 1-(1-naphthylmethyl)-1H-indole-2,3-dione；1-(naphthalen-1-ylmethyl)indole-2,3-dione
• CAS: 79183-21-4
• 化学式: C₁₉H₁₃NO₂
• mdl: MFCD00498556
• 分子量: 287.318
• InChiKey: JZHKGMPFIUHFTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-(naphthalen-1-ylmethyl)indoline-2,3-dione 在 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以70%的产率得到3-hydroxy-1-(naphthalen-1-ylmethyl)indolin-2-one
  参考文献：
  名称：

  Iridium-Catalyzed Enantioselective and Diastereoselective Allylation of Dioxindoles: A One-Step Synthesis of 3-Allyl-3-hydroxyoxindoles

  摘要：

  An iridium-catalyzed asymmetric allylation of dioxindoles, 3-hydroxyoxindoles, regulated by prosthetic groups has been accomplished under mild conditions. The methodology is applicable to a diverse array of 3-hydroxyoxindole and cinnamyl acetate substrates. A range of 3-ally'-3-hydroxyoxindoles containing vicinal tetrasubstituted and trisubstituted stereocenters can be efficiently synthesized in one-step with excellent enantioselectivity (up to >99% enaniomeric excess (ee)) and good diastereoselectivity (up to 11:1 diastereomeric ratio (dr)).

  DOI：

  10.1021/acs.orglett.8b02655
• 作为产物：
  描述：

  靛红 、 1-溴甲基萘 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以40%的产率得到1-(naphthalen-1-ylmethyl)indoline-2,3-dione
  参考文献：
  名称：

  A Novel Cr3+ Fluorescence Turn-On Probe Based on Rhodamine and Isatin Framework

  摘要：

  基于罗丹明-靛红杂化分子架构，通过靛红衍生物与罗丹明酰肼的缩合反应合成了一种新型开启荧光染料（E）-3′，6′-双（二乙基氨基）-2-（（1-（萘-2-基甲基）-2-氧代吲哚啉-3-亚基）氨基）螺[异吲哚啉-1，9′-咕吨]-3-酮（RBNI）。该染料RBNI在含水乙腈介质中对Cr3+离子的识别具有选择性和灵敏性，优于其他测试金属离子。传感器在与Cr3+复合时表现出强烈的荧光增强，并同时发生从无色到粉红色的颜色变化。光谱学研究表明RBNI与Cr3+离子之间存在1:1的结合化学计量关系，这一结论通过电喷雾电离质谱（ESI-MS）得到验证。通过该染料计算得到Cr3+离子的检测限为2.4微米。此外，本研究还展示了该染料在监测池塘水和自来水样品中Cr3+离子的应用潜力。

  DOI：

  10.1007/s10895-015-1684-0

文献信息

• Diversity-oriented synthesis of spiro-oxindole-based 2,5-dihydropyrroles via three-component cycloadditions and evaluation on their cytotoxicity
  作者：Wei Tan、Xiao-Tong Zhu、Shu Zhang、Gui-Juan Xing、Ren-Yi Zhu、Feng Shi

  DOI：10.1039/c3ra40874d

  日期：——

  The construction of a spiro-oxindole-based 2,5-dihydropyrrole scaffold with potential bioactivity has been established via an efficient three-component reaction of isatin, amino-ester and alkyne. This protocol represents the first 1,3-dipolar cycloaddition of electron-deficient alkynes with isatin-derived azomethine ylides, providing an easy access to spiro-oxindole-based 2,5-dihydropyrroles with structural diversity in high yields (up to 99%). In addition, the bioscreen of these new spiro-dihydropyrroles has led to the finding of sixteen compounds with promising cytotoxicity to MCF-7 cells.

  通过异吲哚酮、氨基酯和炔的三组分反应，建立了具有潜在生物活性的螺-羟吲哚基-2,5-二氢吡咯骨架。该方法首次实现了缺电子炔烃与异吲哚酮衍生的偶氮亚甲基叶立德的1,3-偶极环加成反应，为高收率（高达99%）获得结构多样的螺-羟吲哚基-2,5-二氢吡咯提供了一条简便途径。此外，对这些新型螺-二氢吡咯的生物筛选发现了十六个化合物对MCF-7细胞显示出有前景的细胞毒性。
• Highly efficient synthesis of triazolo[1,2-a]indazole-triones and novel spiro triazolo[1,2-a]indazole-tetraones under solvent-free conditions
  作者：Alireza Hasaninejad、Abdolkarim Zare、Mohsen Shekouhy

  DOI：10.1016/j.tet.2010.11.029

  日期：2011.1

  A new, convenient, and high yielding procedure for the synthesis of triazolo[1,2-a]indazole-triones by the condensation reaction between dimedone, aryl aldehydes, and ueazoles in the presence of a catalytic amount of sulfonated polyethylene glycol (PEG-SO3H) as a highly stable and reusable eco-friendly degradable polymeric catalyst is described under solvent-free conditions. This procedure has also

  为三唑的合成中的新的，方便，和高产过程[1,2一]吲唑三酮在磺化聚乙二醇的催化量的双甲酮存在下，芳基醛和ueazoles之间的缩合反应（PEG-在无溶剂条件下描述了作为高度稳定且可重复使用的生态友好型可降解聚合物催化剂的SO 3 H）。该方法也已经成功地用于合成新型螺三唑[1,2 - a ]吲唑-四酮。
• [EN] NOVEL COMPOUNDS USEFUL AS POLY(ADP-RIBOSE) POLYMERASE (PARP) INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS UTILES EN TANT QU'INHIBITEURS DE LA POLY(ADP-RIBOSE) POLYMÉRASE (PARP)
  申请人：RHIZEN PHARMACEUTICALS AG

  公开号：WO2021220120A1

  公开（公告）日：2021-11-04

  The present invention provides novel poly(ADP-ribose) polymerase (PARP) inhibitors, methods of preparing them, pharmaceutical compositions containing them and methods for the treatment, prevention and/or amelioration of PARP mediated diseases or disorders using them. In particular, the compounds described herein are useful for the treatment of carcinoma of the breast, ovarian cancer, carcinoma of the liver, carcinoma of the lung, small cell lung cancer, esophageal cancer, gall bladder cancer, pancreatic cancer and stomach cancer.

  本发明提供了新型聚(ADP核糖)聚合酶（PARP）抑制剂，其制备方法，含有它们的药物组合物以及使用它们治疗、预防和/或改善PARP介导的疾病或紊乱的方法。具体来说，本文描述的化合物对于治疗乳腺癌、卵巢癌、肝癌、肺癌、小细胞肺癌、食管癌、胆囊癌、胰腺癌和胃癌是有用的。
• Discovery of XEN907, a spirooxindole blocker of NaV1.7 for the treatment of pain
  作者：Sultan Chowdhury、Mikhail Chafeev、Shifeng Liu、Jianyu Sun、Vandna Raina、Ray Chui、Wendy Young、Rainbow Kwan、Jianmin Fu、Jay A. Cadieux

  DOI：10.1016/j.bmcl.2011.04.088

  日期：2011.6

  series of NaV1.7 blockers were developed. Following the elimination of undesirable structural features, preliminary optimization of the oxindole C-3 and N-1 substituents afforded the simplified analogue 9b, which demonstrated a 10-fold increase in target potency versus the original HTS hit. A scaffold rigidification strategy then led to the discovery of XEN907, a novel spirooxindole NaV1.7 blocker. This

  从通过高通量筛选活动确定的羟吲哚2a开始，开发了一系列Na V 1.7阻滞剂。在消除了不良的结构特征之后，对羟吲哚C-3和N-1取代基进行了初步优化，得到了简化的类似物9b，与原始HTS命中相比，该类似物的目标效能提高了10倍。脚手架的加固策略随后导致了XEN907的发现，XEN907是一种新型螺氧吲哚Na V 1.7阻滞剂。这种先导化合物的效能又提高了10倍，代表了进一步优化工作的有希望的结构。
• Chiral CNN Pincer Palladium(II) Complexes with 2-Aryl-6-(oxazolinyl)pyridine Ligands: Synthesis, Characterization, and Application to Enantioselective Allylation of Isatins and Suzuki–Miyaura Coupling Reaction
  作者：Tao Wang、Xin-Qi Hao、Juan-Juan Huang、Kai Wang、Jun-Fang Gong、Mao-Ping Song

  DOI：10.1021/om400945d

  日期：2014.1.13

  1-naphthyl) ligands 2a–f were conveniently prepared from commercially available 6-bromo-2-picolinaldehyde in two steps. Reaction of 2a–f with PdCl2 in toluene in the presence of sodium bicarbonate afforded the corresponding CNN pincer Pd(II) complexes 3a–f via aryl C–H bond activation of the related ligands. All of the new compounds have been fully characterized by elemental analysis (MS for ligands), 1H

  从市售的6-溴-2-吡啶啉醛中分两步方便地制备了一系列手性2-芳基-6-（恶唑啉基）吡啶（芳基=苯基或1-萘基）配体2a – f。在碳酸氢钠存在下，2a – f与PdCl 2在甲苯中的反应通过相关配体的芳基C–H键活化，提供了相应的CNN钳位Pd（II）配合物3a – f。所有新化合物均已通过元素分析（配体的质谱），1 H和13 C NMR和IR光谱进行了全面表征。此外，Pd（II）配合物3c – f的分子结构已经通过X射线单晶衍射确定。所获得的手性钳催化剂成功地用于靛红与烯丙基三丁基锡的不对称烯丙基化，以高收率得到相应的3-烯丙基-3-羟基羟吲哚，对映选择性高达86％ee。这些钳子还可以催化不对称的Suzuki-Miyaura偶联反应，以高收率和良好的立体选择性（高达ee的68％）提供轴向手性联芳基产品。