3-azido-4-(3-indolyl)-pyrroline-2,5-dione | 321567-49-1

• 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-azido-4-(3-indolyl)-pyrroline-2,5-dione
• 英文别名: 3-azido-4-(1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 321567-49-1
• 化学式: C₁₂H₇N₅O₂
• 分子量: 253.22
• InChiKey: GYRKPNAZLRGFES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-azido-4-(3-indolyl)-pyrroline-2,5-dione 在 palladium on activated charcoal 作用下， 以 四氢呋喃 、 邻二甲苯 为溶剂， 反应 49.0h， 生成 8-Phenyl-4,7,10-triazatetracyclo[7.7.0.02,6.011,16]hexadeca-1,6,8,11,13,15-hexaene-3,5-dione
  参考文献：
  名称：

  Pyrrolo[3,4-c]-β-carboline-diones as a novel class of inhibitors of the platelet-derived growth factor receptor kinase

  摘要：

  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.

  DOI：

  10.1016/s0223-5234(00)00140-9
• 作为产物：
  描述：

  3-bromo-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以69%的产率得到3-azido-4-(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 of pyrrolo[3′,4′:2,3]azepino[4,5,6-<i>cd</i>]indole-8,10-diones
  作者：Siavosh Mahboobi、Stella Eluwa、Markus Koller、Alfred Popp、Dieter Schollmeyer

  DOI：10.1002/jhet.5570370526

  日期：2000.9

  condensed with various aldehydes and ketones to the cor responding imines. Under Pictet-Spengler conditions, the latter do not cyclize to pyrrolo-β-carbolines, but readily yield pyrrolo[3′,4′:2,3]azepino[4,5,6-cd]indole-8,10-diones.

  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。
• 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.
• Synthesis and Cytotoxicity of Novel 3-amido-4-indolylmaleimide Derivatives
  作者：Sheng Yin Zhao、Shi Wei Mou、Zhi Long Chen、Yun Yue、Yun Sun

  DOI：10.3184/030823409x430202

  日期：2009.3

  A series of novel 3-amido-4-indolylmaleimides have been synthesised from succinimide in five steps sequence consisting of bromination, indole addition, azide substitution, reduction and selective acylation. Cytotoxicity was evaluated for the products against cervical cancer Hela cell lines and human hepatocellular cancer SMMC 7721 cell line by standard MTT assay in vitro. Some of these compounds showed moderate cytotoxic potencies.

  本研究以琥珀酰亚胺为原料，通过溴化、吲哚加成、叠氮取代、还原和选择性酰化五个步骤合成了一系列新型 3-氨基-4-吲哚马来酰亚胺。通过标准的 MTT 法，在体外评估了这些产品对宫颈癌 Hela 细胞系和人肝癌 SMMC 7721 细胞系的细胞毒性。其中一些化合物显示出中等程度的细胞毒性。