9-ethyl-β-carboline-1-carboxaldehyde | 1613078-21-9

• 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: 9-ethyl-β-carboline-1-carboxaldehyde
• 英文别名: 9-ethyl-9,9 a-dihydro-4aH-pyrido[3,4-b]indole-1-carbaldehyde；9-ethyl-β-carboline-1-carbaldehyde；9-Ethylpyrido[3,4-b]indole-1-carbaldehyde；9-ethylpyrido[3,4-b]indole-1-carbaldehyde
• CAS: 1613078-21-9
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: UZWYQMVQLSYCHO-UHFFFAOYSA-N

物化性质

• 沸点：
  351.9±35.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-ethyl-β-carboline-1-carboxaldehyde 在 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 N,N-bis[(9-ethyl-β-carboline-1-yl)methyl]propyl-1,3-diamine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel alkyl diamine linked bivalent β-carbolines as angiogenesis inhibitors

  摘要：

  We have synthesized and evaluated a series of novel alkyl diamine linked bivalent beta-carbolines as potent angiogenesis inhibitors. The results demonstrated that most bivalent beta-carbolines exhibited significant antiproliferative effects against human umbilical vein cell lines EA.HY926. Compound 4m was found to be the most potent antiproliferative agent with IC50 value of 2.16 mu M against EA.HY926 cell lines. Mechanism investigations revealed that compound 4m could significantly inhibit EA.HY926 cells migration and tube formation in a dose-dependent manner. Moreover, compound 4m also showed obvious angiogenesis inhibitory effects in CAM assay, and the antiangiogenetic potency was more potent than the reference drug Endostar. The bivalent beta-carbolines might be served as candidates for the development of vascular targeting antitumor drugs. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.08.050
• 作为产物：
  描述：

  DL-色氨酸 在 N-氯代丁二酰亚胺 、 caesium carbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 9-ethyl-β-carboline-1-carboxaldehyde
  参考文献：
  名称：

  一种AcOH介导的无金属合成双咔啉和咪唑并吡啶并吲哚衍生物并评估其光物理性质的方法

  摘要：

  一个的AcOH介导的简洁，原子的经济和环境上可持续的串联策略已被配制成访问高荧光（Φ ˚F高达40％）N -稠合二咔啉，imidazopyrido [3,4 b ]吲哚和咪唑并[1,2 5- a ]吡啶通过一次操作形成三个C–N键。反应的多组分特性，易于执行的反应条件，简单的纯化步骤以及所提供产物的优异发光性能提供了广阔的范围。

  DOI：

  10.1039/c8ob02705f

文献信息

• Synthesis of novel β-carboline based chalcones with high cytotoxic activity against breast cancer cells
  作者：Shikha S. Chauhan、Anup K. Singh、Sanjeev Meena、Minaxi Lohani、Akhilesh Singh、Rakesh K. Arya、Srikanth H. Cheruvu、Jayanta Sarkar、Jiaur R. Gayen、Dipak Datta、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2014.04.109

  日期：2014.7

  series of novel β-carboline based chalcones was synthesized and evaluated for their cytotoxic activity against a panel of human cancer cell lines. Among them we found that two of the compounds 7c and 7d, showed marked anti-proliferative activity in a panel of solid tumor cell lines with highest effect in breast cancer. The compounds 7c and 7d showed an IC50 of 2.25 and 3.29 μM, respectively against human

  合成了一系列新型的基于β-咔啉的查耳酮，并评估了它们对一组人类癌细胞系的细胞毒活性。在它们当中，我们发现化合物7c和7d中的两种在一组实体瘤细胞系中显示出显着的抗增殖活性，对乳腺癌的影响最大。化合物7c和7d对人乳腺癌MCF-7细胞株的IC 50分别为2.25和3.29μM。此外，化合物7c在乳腺癌细胞中明显诱导DNA片段化和凋亡。
• Iodine Catalysed Synthesis of Luminescent β-Carboline Tethered Thiazolo[4,5-<i>c</i> ]carbazole and Naphtho[2,1-<i>d</i> ]thiazole Derivatives and Estimation of their Light Emitting Properties
  作者：Manpreet Singh、Pamita Awasthi、Virender Singh

  DOI：10.1002/ejoc.201901908

  日期：2020.2.28

  This methodology provides an easy access to gram scale synthesis of highly fluorescent β‐carboline tethered thiazolo[4,5‐c]carbazoles and benzothiazole derivatives in excellent yields. The synthesized analogues may find wide application in medicinal chemistry with potential scope as anticancer agents or DNA staining agents and in material science as fluorescent probes and chemosensors.

  这种方法可以轻松获得以克级合成高荧光度的β-咔啉系链的噻唑并[4,5- c ]咔唑和苯并噻唑衍生物，且收率很高。合成的类似物可能会在药物化学中得到广泛应用，其潜在范围可以用作抗癌剂或DNA染色剂，以及在材料科学中可以用作荧光探针和化学传感器。
• A metal-free approach towards synthesis of β-carboline C1 substituted Pyrido(2,3-c)carbazole derivatives (nitramarine analogues) through A3-coupling and estimation of their light emitting properties
  作者：Manpreet Singh、Vaishali、Sunit Kumar、Rahul Jamra、Satyendra K. Pandey、Virender Singh

  DOI：10.1016/j.tet.2020.131640

  日期：2020.11

  A simple and efficient metal-free methodology is presented to access fluorescent β-carboline tethered pyrido(2,3-c)carbazole derivatives (Nitramarine analogues) via A3-coupling of 1-formyl-9H-β-carbolines, 3-amino-9-ethylcarbazole, and terminal alkynes. The advantages of this approach are operationally simple procedure, use of non-toxic and inexpensive catalyst (I2), broad substrate scope, and good

  一个简单的和有效的不含金属的方法被呈现给访问荧光β咔啉系留式的吡啶并（2,3- c ^经由A）的咔唑衍生物（Nitramarine类似物）3的1-甲酰基- 9 -耦合ħ -β咔啉，3-氨基-9-乙基咔唑和末端炔烃。这种方法的优点是操作简单，使用无毒且价格便宜的催化剂（I 2），广泛的底物范围和良好的产品收率。此外，这些产品显示出与量子产率（Φ优异的发光特性˚F高达60％）。
• Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties
  作者：Dharmender Singh、Vipin Kumar、Virender Singh

  DOI：10.3762/bjoc.16.146

  日期：——

  A robust transition-metal-free strategy is presented to access novel β-carboline-tethered benzothiophenone derivatives from 1(3)-formyl-β-carbolines using elemental sulfur activated by Et₃N/DMSO. This expeditious catalyst-free reaction proceeds through the formation of β-carboline-based 2-nitrochalcones followed by an incorporation of sulfur to generate multifunctional β-carboline-linked benzothiophenones in good to excellent yields. The synthetic strategy could also be extended towards the synthesis of β-carboline-linked benzothiophenes. Moreover, the afforded products emerged as promising fluorophores and displayed excellent light-emitting properties with quantum yields (Φ_F) up to 47%.

  本文提出了一种稳健的无过渡金属策略，利用元素硫在 Et3N/DMSO 的活化作用下，从 1(3)-formyl-β-carbolines 中获得新型 β-carboline拴系苯并噻吩酮衍生物。这种快速的无催化剂反应通过形成以 β-咔啉为基础的 2-硝基查耳酮，然后掺入硫元素，生成多功能的 β-咔啉连接的苯并噻吩酮，收率良好甚至极佳。该合成策略还可扩展用于合成 β-咔啉连接的苯并噻吩。此外，所得到的产物作为有前途的荧光体，显示出优异的发光特性，量子产率（ΦF）高达 47%。
• A transition metal-free approach towards the regioselective synthesis of β-carboline tethered pyrroles and 2,3-dihydro-1<i>H</i>-pyrroles
  作者：Manpreet Singh、Avijit Kumar Paul、Virender Singh

  DOI：10.1039/d0nj02315a

  日期：——

  An efficient metal-free approach has been devised for the synthesis of novel β-carboline C-1 tethered 2,3-dihydropyrroles and pyrroles via one-pot assembly involving 1-formyl β-carbolines, aryl methyl ketones, and isonitriles. The reaction advances through the formation of β-carboline linked enones followed by [3+2] cycloaddition with isonitriles. This methodology features an operationally simple procedure

  已经设计了一种有效的无金属方法，用于通过涉及1-甲酰基β-咔啉，芳基甲基酮和异腈的一锅装配来合成新型β-咔啉C-1束缚的2，3-二氢吡咯和吡咯。反应通过形成β-咔啉连接的烯酮进行，然后与异腈进行[3 + 2]环加成反应。该方法具有操作简单，多组分，高原子经济性，底物范围广，反应时间短，区域选择性高，产率高等特点。通过合成具有显着多样性的34种新化合物的文库，举例说明了该方法的范围。