9-benzyl-9H-pyrido[3,4-b]indole-1-carbaldehyde | 203717-13-9

• 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-benzyl-9H-pyrido[3,4-b]indole-1-carbaldehyde
• 英文别名: 9-benzyl-β-carboline-1-carboxaldehyde；9-Benzylpyrido[3,4-b]indole-1-carbaldehyde
• CAS: 203717-13-9
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: UYVRBXKAKYGCGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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-benzyl-9H-pyrido[3,4-b]indole-1-carbaldehyde 在 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-[N-(2-diethylamino-ethyl)-aminomethyl]-9-benzyl-β-carboline
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,9-disubstituted β-carbolines as potent DNA intercalating and cytotoxic agents

  摘要：

  A series of novel 1,9-disubstituted beta-carbolines was designed, synthesized and evaluated as cytotoxic and DNA intercalating agents. Compounds 7b, 7c, 8b and 8c exhibited the most potent cytotoxic activities with IC50 values of lower than 20 mu M against ten human tumor cell lines. The results indicated that (1) the 3-chlorobenzyl and 3-phenylpropyl substituents in position-9 of beta-carboline nucleus were the suitable pharmacophoric group giving rise to significant antitumor agents; (2) the length of the alkylamino side chain moiety affected their cytotoxic potencies, and three CH2 units were more favorable. In addition, these compounds were found to exhibit remarkable DNA intercalating effects. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.027
• 作为产物：
  描述：

  L-色氨酸 在 N-氯代丁二酰亚胺 、 碘 、 caesium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.75h， 生成 9-benzyl-9H-pyrido[3,4-b]indole-1-carbaldehyde
  参考文献：
  名称：

  通过A 3偶联合成β-咔啉C1取代的Pyrido（2,3- c）咔唑衍生物（硝马蓝类似物）的无金属方法并估算其发光性能

  摘要：

  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％）。

  DOI：

  10.1016/j.tet.2020.131640

文献信息

• 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。
• 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%。
• Molecular hybrid design, synthesis, in vitro and in vivo anticancer evaluation, and mechanism of action of N-acylhydrazone linked, heterobivalent β-carbolines
  作者：Liang Guo、Xiaofei Chen、Wei Chen、Qin Ma、Wenxi Fan、Jie Zhang、Bin Dai

  DOI：10.1016/j.bioorg.2020.103612

  日期：2020.3

  cytotoxic activity of the synthesized compounds was evaluated against normal EA.HY926 cells and five cancer cell lines: LLC (Lewis lung carcinoma), BGC-823 (gastric carcinoma), CT-26 (murine colon carcinoma), Bel-7402 (liver carcinoma), and MCF-7 (breast carcinoma). Compound 10e, with an IC50 value of 2.41 μM against EA.HY926 cells, was the most potent inhibitor. It showed cytotoxicity against all five

  设计了一系列由N-酰基hydr连接的异二价β-咔啉衍生物，并按九步反应顺序由1-色氨酸合成。该努力导致了高收率的异二价β-咔啉10a-t。目标化合物通过1H NMR，13C NMR和高分辨率质谱（HRMS）进行表征。评估了合成化合物对正常EA.HY926细胞和5种癌细胞系的体外细胞毒性活性：LLC（刘易斯肺癌），BGC-823（胃癌），CT-26（鼠结肠癌），Bel-7402 （肝癌）和MCF-7（乳腺癌）。化合物10e对EA.HY926细胞的IC50值为2.41μM，是最有效的抑制剂。它对鼠类和人类这五种不同来源的癌细胞系均显示出细胞毒性，IC50值为4.2±0。7至18.5±3.1μM。对结构-活性关系的研究表明，R9'-位对取代基的细胞毒性活性的影响遵循2,3,4,5,6-全氟苯基甲基> 4-氟苄基> 3-苯基丙基的趋势。还在小鼠中评估了所选化合物的抗肿瘤功效。化合物10e表现出有效
• 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。
• In(OTf)₃catalysed an expeditious synthesis of β-carboline–imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrazine conjugates
  作者：Nisha Devi、Dharmender Singh、Honey Honey、Satbir Mor、Sandeep Chaudhary、Ravindra K. Rawal、Vipin Kumar、Asim K. Chowdhury、Virender Singh

  DOI：10.1039/c6ra04841b

  日期：——

  β-carboline–imidazoazine conjugates were designed and a small library of compounds integrating both the pharmacophores was constructed with 4-points of diversity by using the In(OTf)3 assisted Groebke–Blackburn–Bienayme multicomponent strategy. The methodology was found to be simple and convenient for the efficient syntheses of β-carboline–imidazo[1,2-a]azine conjugates. The present synthetic protocol

  在自然界中普遍存在着含β-咔啉的生物碱，而咪唑并[1,2- a ]吡啶核被掺入到各种合成的商业药物和具有生物学危害的部分中。在此基础上，设计了新的β-咔啉-咪唑嗪偶联物，并使用In（OTf）3辅助的Groebke-Blackburn-Bienayme多组分策略构建了一个整合了两个药效基团的小化合物库，具有4个点的多样性。发现该方法简单有效，可高效合成β-咔啉-咪唑并[1,2- a ]嗪共轭物。本合成方案具有几个优点，例如操作简单，可观的原子经济性，短的反应时间和容易的纯化步骤。