1-[2-(1H-吲哚-3-基)乙基]吡咯烷-2,5-二酮 | 59048-75-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-[2-(1H-吲哚-3-基)乙基]吡咯烷-2,5-二酮
• 英文名称: N-[2-(1H-indol-3-yl)ethyl]pyrrolidine-2,5-dione
• 英文别名: 1-[2-(1H-indol-3-yl)ethyl]pyrrolidin-2,5-dione；N-(β-indolylethyl)succinimide；N-[2-(indol-3-yl)ethyl]succinimide；N-succinoimidotryptamine；N-succinimidotryptamine；1-(2-(1H-Indol-3-yl)ethyl)pyrrolidine-2,5-dione；1-[2-(1H-indol-3-yl)ethyl]pyrrolidine-2,5-dione
• CAS: 59048-75-8
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: HYENFSOYXDDPGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[2-(1H-吲哚-3-基)乙基]吡咯烷-2,5-二酮 在 triethyloxonium fluoroborate 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 61.5h， 以53%的产率得到(+/-)-harmacine
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 10: SAR Studies on Azecine-type Dopamine Receptor Ligands by Functional Screening at Human Cloned D₁, D_2L, and D₅ Receptors with a Microplate Reader Based Calcium Assay Lead to a Novel Potent D₁/D₅ Selective Antagonist

  摘要：

  On the basis of the benz[d]indolo[2,3-g]azecine derivative I (LE300), structure-activity relations were investigated in order to identify the pharmacophore in this new class of ligands. Various structural modifications were performed and the inhibitory activities at human cloned D-1, D-2L, and D-5 receptors were measured by using a simple fluorescence microplate reader based calcium assay. Subsequently, the affinities of active compounds were estimated by radioligand binding experiments. Deleting one of the aromatic rings as well as replacing it by a phenyl moiety abolishes the inhibitory activities almost completely. Contraction of the 10-membered central ring decreases them significantly. The replacement of indole by thiophene or N-methylpyrrole reduces the inhibitory activity, whereas replacing the indole by benzene increases it. Finally, the hydroxylated dibenz[d,g]azecine derivative 11d (LE404) was found to be more active than the lead I in the functional calcium assay as well as in radioligand displacement experiments.

  DOI：

  10.1021/jm050846j
• 作为产物：
  描述：

  (Z)-4-[2-(1H-indol-3-yl)ethylamino]-4-oxobut-2-enoic acid 在 盐酸 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 1-[2-(1H-吲哚-3-基)乙基]吡咯烷-2,5-二酮
  参考文献：
  名称：

  First Triphenylphosphine PromotedReduction of Maleimides to Succinimides

  摘要：

  三苯基膦（TPP）在回流甲醇中能有效地将马来酰亚胺 1a-g 还原成相应的琥珀酰亚胺 2a-g，而且收率很高。据观察，一些从芳香卤素化合物 1h-j 中得到的马来酰亚胺通过该反应转化为相应的琥珀酰亚胺酸甲酯 3a-c。

  DOI：

  10.1055/s-2003-40523

文献信息

• SUBSTITUTED HETEROARYL DERIVATIVES
  申请人：Zemolka Saskia

  公开号：US20100009986A1

  公开（公告）日：2010-01-14

  The invention relates to substituted heteroaryl derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted heteroaryl derivatives for producing medicaments.

  这项发明涉及替代杂环芳基衍生物，涉及其生产方法，含有该化合物的药物以及利用替代杂环芳基衍生物生产药物的用途。
• Unified Approach to the Spiro(pyrrolidinyl-oxindole) and Hexahydropyrrolo[2,3-<i>b</i>]indole Alkaloids: Total Syntheses of Pseudophrynamines 270 and 272A
  作者：Subhadip De、Mrinal Kanti Das、Subhajit Bhunia、Alakesh Bisai

  DOI：10.1021/acs.orglett.5b03082

  日期：2015.12.4

  enantioenriched 2-oxindoles having all-carbon quaternary stereocenters. A common strategy involving a thio-urea catalyzed aldol reaction is employed for the total synthesis of both spiro(pyrrolidinyl-oxindole) and hexahydropyrrolo[2,3-b]indole alkaloids.

  从具有全碳四元立体中心的对映体富集的2-氧吲哚开始，获得了结构上令人关注的异戊烯化吡咯并吲哚生物碱（-）-伪苯丙胺272A（3d）和270（3b）的第一个对映选择性全合成。螺（吡咯烷基-氧吲哚）和六氢吡咯并[2，3- b ]吲哚生物碱的全合成采用了涉及硫脲催化的醛醇缩合反应的通用策略。
• The Chemistry of Indoles. CIII. Simple Syntheses of Serotonin, N-Methylserotonin, Bufotenine, 5-Methoxy-N-methyltryptamine, Bufobutanoic Acid, N-(Indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and Lespedamine Based on 1-Hydroxyindole Chemistry.
  作者：Masanori SOMEI、Fumio YAMADA、Takashi KURAUCHI、Yoshiyuki NAGAHAMA、Masakazu HASEGAWA、Koji YAMADA、Sakiko TERANISHI、Haruhiko SATO、Chikara KANEKO

  DOI：10.1248/cpb.49.87

  日期：——

  Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.

  本文描述了利用1-羟色胺的选择性亲核取代反应，合成新型简单物质的方法，这些物质包括：血清素（1a）、N-甲基血清素（1b）、蟾毒色胺（1c）、5-甲氧基-N-甲基色胺（2a）、蟾毒色酸（3a）、N-(吲哚-3-基)甲基-5-甲氧基-N-甲基色胺（4）和莱斯佩达明（5）。此外，还报道了有效的5-苄氧基色胺和1-甲氧基-2-氧吲哚合成方法。
• Friedel–Crafts alkylations of electron-rich aromatics with 3-hydroxy-2-oxindoles: scope and limitations
  作者：Lakshmana K. Kinthada、Santanu Ghosh、K. Naresh Babu、Mohd. Sharique、Soumava Biswas、Alakesh Bisai

  DOI：10.1039/c4ob01264j

  日期：——

  A Lewis acid-catalyzed nucleophilic addition of electron rich aromatics with 3-hydroxy-2-oxindoles 5 was developed. The reaction is believed to proceed through the 2H-indol-2-one ring system 9, which eventually reacts with various electron-rich aromatics to afford a variety of 2-oxindoles with an all-carbon quaternary center at the pseudobenzylic position (4, 8, 13, and 16) in high yields. The methodology provides an expeditious route to the tetracyclic core (3) of diazonamide (1), and azonazine (2) as well as the tricyclic core of asperazine (6a), idiospermuline (6b), and calycosidine (6c) viz. C(3a)-arylpyrroloindolines 7 having an all-carbon quaternary center on further synthetic elaboration.

  开发了一种路易斯酸催化的富电子芳香化合物与3-羟基-2-氧吲哚 5 的亲核加成反应。该反应被认为是通过2H-吲哚-2-酮环系 9 进行的，最终与各种富电子芳香化合物反应，生成多种具有全碳季铵中心的2-氧吲哚（4、8、13和16），产率高。这一方法提供了合成二氮酰胺（1）和氮杂啶（2）的四环核心（3）以及某些三环核心的高效途径，如asperazine（6a）、idiospermuline（6b）和calycosidine（6c），即在进一步合成扩展下具有全碳季铵中心的C(3a)-芳基吡咯吲哚类化合物 7。
• Syntheses of fused tetrahydro-β-carboline analogues through imide carbonyl activation using BBr3: Evidence for the involvement of fused cyclic N-acyliminium ion intermediate
  作者：SELVARAJ MANGALARAJ、JAYARAMAN SELVAKUMAR、CHINNASAMY RAMARAJ RAMANATHAN

  DOI：10.1007/s12039-015-0836-8

  日期：2015.5

  The fused cyclic N-acyliminium ion generated during the imide carbonyl activation reaction of phenethylphthalimide was confirmed by single crystal X-ray diffraction. The Lewis acid assisted imide carbonyl activation methodology was successfully extended to synthesize fused tetrahydro-β-carboline units from the corresponding N-indolylethylimides.

  单晶 X 射线衍射证实了在苯乙基邻苯二甲酰亚胺的亚胺羰基活化反应中生成的融合环 N-酰亚胺离子。路易斯酸辅助亚胺羰基活化方法被成功地扩展到从相应的 N-吲哚乙亚胺合成融合的四氢-β-咔啉单元。