3-amino-4-(5-methoxy-3-indolyl)pyrroline-2,5-dione | 222636-71-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-amino-4-(5-methoxy-3-indolyl)pyrroline-2,5-dione
• 英文别名: 3-amino-4-(5-methoxy-1H-indol-3-yl)-1H-pyrrole-2,5-dione；3-amino-4-(5-methoxy-1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 222636-71-7
• 化学式: C₁₃H₁₁N₃O₃
• 分子量: 257.249
• InChiKey: SIXVVMZYEBJQKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-4-(5-methoxy-3-indolyl)pyrroline-2,5-dione 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 5-methoxy-6-(3,4,5-trimethoxyphenyl)-2,6,7,8,9,10-hexahydro-pyrrolo[3',4':2,3]azepino[4,5,6-cd]indole-8,10-dione
  参考文献：
  名称：

  吡咯并[3'，4'：2,3] azepino [4,5,6 - cd ]吲哚-8,10-二酮的合成†

  摘要：

  将3-氨基-4-（3-吲哚基）吡咯啉-2,5-二酮与各种醛和酮缩合为可响应cor的亚胺。在Pictet-Spengler条件下，后者不会环化为吡咯并-β-咔啉，但很容易产生吡咯并[3'，4'：2,3] azepino [4,5,6- cd ]吲哚-8,10-二酮。

  DOI：

  10.1002/jhet.5570370526
• 作为产物：
  描述：

  3-bromo-4-(5-methoxy-3-indolyl)-1H-pyrrole-2,5-dione 在 sodium azide 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 3-amino-4-(5-methoxy-3-indolyl)pyrroline-2,5-dione
  参考文献：
  名称：

  吡咯并[3'，4'：2,3] azepino [4,5,6 - cd ]吲哚-8,10-二酮的合成†

  摘要：

  将3-氨基-4-（3-吲哚基）吡咯啉-2,5-二酮与各种醛和酮缩合为可响应cor的亚胺。在Pictet-Spengler条件下，后者不会环化为吡咯并-β-咔啉，但很容易产生吡咯并[3'，4'：2,3] azepino [4,5,6- cd ]吲哚-8,10-二酮。

  DOI：

  10.1002/jhet.5570370526

文献信息

• Synthesis and Biological Evaluation of 3-Chloro-4-(indol-3-yl)-2,5- pyrroledione Derivatives as Antitumor Agents
  作者：Yuchen Lin、Jing Chen

  DOI：10.2174/1570180811310050003

  日期：2013.4.1

  A series of 3-chloro-4-(indol-3-yl)-2,5-pyrroledione derivatives were synthesized and evaluated for their cytotoxic activities in vitro against five human cancer cell lines (K562, A549, ECA-109, KB and SMMC-7721). Most compounds displayed potent cytotoxicity with IC50 values in low micromolar range. The results showed that the existence of the chlorine atom at 3-position on the pyrroledione ring was crucial for the activity. Compound 6a, the most potent one (IC50: 0.67∼3.93 μM), would be a promising template for further development of novel antitumor agents

  合成了一系列3-氯-4-(吲哚-3-基)-2,5-吡咯二酮衍生物，并评估其对五种人癌细胞系（K562、A549、ECA-109、KB和SMMC-7721）的体外细胞毒性活性。大多数化合物表现出强效的细胞毒性，IC50值在低微摩尔范围内。结果表明，吡咯二酮环上3位的氯原子的存在对活性至关重要。化合物6a是最有效的（IC50：0.67∼3.93 μM），将成为进一步开发新型抗肿瘤药物的有前景的模板。
• Novel method and compounds
  申请人：SmithKline Beecham p.l.c.

  公开号：US20040010031A1

  公开（公告）日：2004-01-15

  A method for the treatment of conditions associated with a need for inhibition of GSK-3, such as diabetes, dementias such as Alzheimer's disease and manic depression which method comprises the administration of a pharmaceutically effective, non-toxic amount of a compound of formula (I): 1 or a pharmaceutically acceptable derivative thereof, wherein: R is hydrogen, alkyl, aryl, or aralkyl; R 1 is hydrogen, alkyl, aralkyl, hydroxyalkyl or alkoxyalkyl; R 2 is substituted or unsubstituted aryl or substituted or unsubstituted heterocyclyl; R 3 is hydrogen, substituted or unsubstituted alkyl, cycloalkyl, alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl or aralkyl wherein the aryl moiety is substituted or unsubstituted; or, R 1 and R 3 together with the nitrogen to which they are attached form a single or fused, optionally substituted, saturated or unsaturated heterocylic ring; to a human or non-human mammal in need thereof, and compounds of formula I.

  一种用于治疗与需要抑制GSK-3相关的疾病的方法，例如糖尿病、阿尔茨海默病和躁郁症，该方法包括向需要的人类或非人类哺乳动物投予化学药效、无毒量的化合物(I)的药物，其中：R为氢、烷基、芳基或芳基烷基；R1为氢、烷基、芳基烷基、羟基烷基或烷氧基烷基；R2为取代或未取代的芳基或取代或未取代的杂环烷基；R3为氢、取代或未取代的烷基、环烷基、烷氧基烷基、取代或未取代的芳基、取代或未取代的杂环烷基或芳基烷基，其中芳基部分为取代或未取代；或者，R1和R3与它们连接的氮一起形成单个或融合的、可选择取代的饱和或不饱和杂环环；以及化合物I的药物可接受衍生物。
• Methods and materials for identifying agents which modulate bone remodeling and agents identified thereby
  申请人：Chatterjee-Kishore Moitreyee

  公开号：US20060252045A1

  公开（公告）日：2006-11-09

  The invention discloses compositions, compounds, apparatuses and methods of using them to study bone mineralization and identify agents that regulate bone mineralization. Methods of using bone mineralization gene profiles and signatures for compound screening and research are also disclosed. Reagents for modulating bone mineralization are provided for both therapeutic and research usage.

  本发明揭示了用于研究骨矿化和鉴定调节骨矿化的药物的组合物、化合物、装置和使用方法。还揭示了使用骨矿化基因谱和签名进行化合物筛选和研究的方法。提供了用于调节骨矿化的试剂，可用于治疗和研究。
• Pyrrolo[3,4-c]-β-carboline-diones as a novel class of inhibitors of the platelet-derived growth factor receptor kinase
  作者：S Teller

  DOI：10.1016/s0223-5234(00)00140-9

  日期：2000.4

  Members of the structurally diverse family of beta-carbolines have previously been shown to exhibit a wide range of biological activities. A novel synthetic strategy for generation of beta-carbolines was developed, allowing imido-beta-carbolines to be created in three steps from known compounds. The compounds were screened for inhibition of platelet-derived growth factor (PDGF)-stimulated tyrosine phosphorylation in Swiss 3T3 fibroblasts. A number of the newly synthesized beta-carbolines with moderate to potent inhibitory activity were revealed. The most active derivative, 2,3-dihydro-8,9-dimethoxy-5-(2-methylphenyl)-1H,6H-pyrrolo[3,4-c]pyrido[3,4-b]indole-1,3-dione 2ee, inhibited purified PDGF receptor kinase and PDGF-receptor autophosphorylation in intact cells with IC50 values of 0.4 and 2.6 mu M, respectively. Dione 2ee also inhibited PDGF-stimulated DNA synthesis in Swiss 3T3 fibroblasts with an IC50 of 3.2 mu M. The compound had no effect on Src or epidermal growth factor (EGF) receptor kinase activity and a six-seven-fold higher IC50 for inhibition of basic fibroblast growth factor (bFGF)-stimulated tyrosine phosphorylation or Kit/stem cell factor (SCF) receptor autophosphorylation, indicating a reasonable extent of kinase specificity. Thus, beta-carbolines present a new lead of tyrosine kinase inhibitors with the capacity to selectively interfere with PDGF receptor signal transduction and PDGF-dependent cell growth. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• PYRROLE-2,5-DIONES AS GSK-3 INHIBITORS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1119548A1

  公开（公告）日：2001-08-01