1-(3-bromobenzoyl)-β-carboline | 906067-46-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(3-bromobenzoyl)-β-carboline
• 英文别名: (3-bromophenyl)-(9H-β-carbolin-1-yl)-methanone；(3-Bromophenyl)(9H-beta-carbolin-1-yl)methanone；(3-bromophenyl)-(9H-pyrido[3,4-b]indol-1-yl)methanone
• CAS: 906067-46-7
• 化学式: C₁₈H₁₁BrN₂O
• 分子量: 351.202
• InChiKey: UWCQMZCXNUYULW-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C(Solvent: Ethyl acetate)
• 沸点：
  576.3±40.0 °C(Predicted)
• 密度：
  1.571±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-bromobenzoyl)-β-carboline 、 4-叔丁基苯硼酸 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 以99%的产率得到C₂₈H₂₄N₂O
  参考文献：
  名称：

  Synthesis, crystal structure and biological activity of β-carboline based selective CDK4-cyclin D1 inhibitors

  摘要：

  本文展示了一系列非平面二氢-β-卡巴啉和基于β-卡巴啉的衍生物的设计、合成和生物活性，这些衍生物源自毒性抗癌剂法斯卡普利辛。我们证明这些化合物是CDK4的选择性抑制剂，相较于CDK2，系列中最佳化合物4d的IC50（CDK4-细胞周期蛋白D1）为11 µmol。对部分合成化合物（3b/d和4a–d）进行了晶体学分析，以估计设计抑制剂与模型化合物法斯卡普利辛之间的结构相似性。

  DOI：

  10.1039/b613861f
• 作为产物：
  描述：

  1-(3-bromobenzoyl)-3,4-dihydro-β-carboline 在 氧气 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以99%的产率得到1-(3-bromobenzoyl)-β-carboline
  参考文献：
  名称：

  Regioselective photo-oxidation of 1-benzyl-4,9-dihydro-3H-β-carbolines

  摘要：

  本文展示了一系列基于β-卡波啉的天然产物fascaplysin的类似物的合成；这些化合物是通过1-苄基-4,9-二氢-3H-β-卡波啉的创新光氧化反应作为关键步骤生产的。

  DOI：

  10.1039/b604922b

文献信息

• Synthesis, in vitro anti-inflammatory and cytotoxic evaluation, and mechanism of action studies of 1-benzoyl-β-carboline and 1-benzoyl-3-carboxy-β-carboline derivatives
  作者：Mei-Lin Yang、Ping-Chung Kuo、Tsong-Long Hwang、Wen-Fei Chiou、Keduo Qian、Chin-Yu Lai、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmc.2011.01.034

  日期：2011.3

  In the present study, various 1-substituted and 1,3-disubstituted beta-carboline derivatives were synthesized by a modified single-step Pictet-Spengler reaction. The compounds were examined for cytotoxicity and anti-inflammatory activity, as measured by the inhibition of prostaglandin E-2 (PGE(2)) production and nitric oxide (NO) production. While only two compounds (28 and 31) showed marginal cytotoxicity against four human cancer cell lines, most of the tested compounds exhibited potent inhibitory activity of both NO and PGE(2) production. Moreover, compounds 6 and 16 significantly reduced the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX2), suggesting that beta-carboline analogs can inhibit NO and PGE(2) production at the translational level. In addition, several of the beta-carboline derivatives (1, 2, 48, 11, 13, 22, 25, 27, 31, and 41-43) displayed significant inhibitory activity of superoxide anion (O-2(center dot-)) generation or elastase release compared to the reference compound, with 6 being the most potent. N-Formyl-L-methionyl-phenylalanine (FMLP)-induced phosphorylation of c-Jun N-terminal kinase (JNK) and protein kinase B (AKT) were also inhibited by 6, suggesting that it suppresses human neutrophil functions by inhibiting the activation of JNK and AKT signaling pathways. Therefore, the synthetic 1-benzoyl-3-carboxy beta-carboline analogs may have great potential to be developed as anti-inflammatory agents. (C) 2011 Elsevier Ltd. All rights reserved.