9-benzyl-β-carboline-3-carbaldehyde | 1160060-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-benzyl-β-carboline-3-carbaldehyde
• 英文别名: 9-benzyl-β-carboline-3-carboxaldehyde；9-Benzylpyrido[3,4-b]indole-3-carbaldehyde
• CAS: 1160060-08-1
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: BYGGXLKOFYMZQC-UHFFFAOYSA-N

物化性质

• 沸点：
  450.2±45.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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-β-carboline-3-carbaldehyde 在 hydrazine hydrate 、 manganese(IV) oxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以66%的产率得到9-benzyl-9H-[1,2,3]triazolo[1',5':1,6]pyrido[3,4-b]indole
  参考文献：
  名称：

  一种β-咔啉杂合三唑类化合物及其制备方法、应用

  摘要：

  本发明为一种β‑咔啉杂合三唑类化合物及其制备方法、应用。本发明公开了一类新的化合物—β‑咔啉杂合三唑类化合物，及β‑咔啉杂合三唑类化合物在制备抗肿瘤药物中的应用。本发明的β‑咔啉杂合三唑类化合物为一种新的化合物，具有较好的抗肿瘤活性，可应用于抗肿瘤药物中。

  公开号：

  CN112939973B
• 作为产物：
  描述：

  2,3,4,9-四氢-1H-beta-咔啉-3-甲酸 在 manganese(IV) oxide 、 锂硼氢 、 氯化亚砜 、 sodium hydride 、 sulfur 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.0h， 生成 9-benzyl-β-carboline-3-carbaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of piperazine group-linked bivalent β-carbolines as potential antitumor agents

  摘要：

  一系列具有3-亚甲基单元之间的哌嗪基间隔的二价β-咔啉类化合物被合成，并评估了它们的体外细胞毒活性。化合物7e和7g表现出强大的细胞毒活性。

  DOI：

  10.1039/c5md00312a

文献信息

• Design, Synthesis, and Biological Evaluation of Novel N-Acylhydrazone Bond Linked Heterobivalent β-Carbolines as Potential Anticancer Agents
  作者：Chen、Guo、Ma、Chen、Fan、Zhang

  DOI：10.3390/molecules24162950

  日期：——

  Utilizing a pharmacophore hybridization approach, we have designed and synthesized a novel series of 28 new heterobivalent β-carbolines. The in vitro cytotoxic potential of each compound was evaluated against the five cancer cell lines (LLC, BGC-823, CT-26, Bel-7402, and MCF-7) of different origin—murine and human, with the aim of determining the potency and selectivity of the compounds. Compound 8z

  利用药效团杂交方法，我们设计并合成了一系列新的 28 种新型异二价 β-咔啉。评估了每种化合物对不同来源（鼠类和人）的五种癌细胞系（LLC、BGC-823、CT-26、Bel-7402 和 MCF-7）的体外细胞毒性潜力，目的是确定化合物的效力和选择性。化合物 8z 显示出抗肿瘤活性，半数最大抑制浓度 (IC50) 值为 9.9 ± 0.9、8.6 ± 1.4、6.2 ± 2.5、9.9 ± 0.5 和 5.7 ± 1.2 µM，对测试的五种癌细胞系。此外，使用鸡绒毛尿囊膜 (CAM) 体内模型研究了化合物 8z 对血管生成过程的影响。在 5 μM 的浓度下，化合物 8z 显示出对血管生成的积极影响。
• Bivalent β-Carbolines Inhibit Colorectal Cancer Growth through Inducing Autophagy
  作者：Huihui Zhang、Rihui Cao、Feng Zeng、Wenxi Fan、Liang Guo、Qin Ma、Shaobo Ke

  DOI：10.1248/cpb.c21-00588

  日期：2021.11.1

  In this study, a series of alkyl diamine linked bivalent β-carbolines was synthesized and evaluated as antitumor agent. The results demonstrated that most compounds displayed good antiproliferative activities with IC50 value lower than 10 µM against a panel of human tumor cell lines, and compound 8 was found to be the most potent antiproliferative agent with IC50 value of 1.39, 1.96, 1.42, 1.49, 1.32, 1.96 and 1.63 µM against human breast cancer cell line (MCF-7), human adenocarcinoma cell line (769-P), human malighant melanoma cell line (A375), human ovarian cancer cell line (SK-OV-3), human colon carcinoma cell line (HCT-116), human gastric cancer cell line (BGC-823) and human esophageal squamous carcinoma cell line (Eca-109), respectively. Further investigations on mechanism of action of this class of compound demonstrated that the representative compound 8 inhibited colorectal cancer growth through inducing autophagy.

  在本研究中，合成了一系列烷基二胺连接的二价β-咔啉并评估其抗肿瘤剂的作用。结果表明，大多数化合物对一组人肿瘤细胞系表现出良好的抗增殖活性，IC50值低于10μM，并且发现化合物8是最有效的抗增殖剂，IC50值分别为1.39、1.96、1.42、1.49、 1.32、1.96 和 1.63μM，针对人乳腺癌细胞系 (MCF-7)、人腺癌细胞系 (769-P)、人恶性黑色素瘤细胞系 (A375)、人卵巢癌细胞系 (SK-OV-3)、分别为人结肠癌细胞系（HCT-116）、人胃癌细胞系（BGC-823）和人食管鳞癌细胞系（Eca-109）。对该类化合物作用机制的进一步研究表明，代表性化合物8通过诱导自噬抑制结直肠癌的生长。
• Design, synthesis and biological evaluation of novel alkyl diamine linked bivalent β-carbolines as angiogenesis inhibitors
  作者：Qing Chen、Wei Chen、Wenxi Fan、Liang Guo、Qin Ma、Xiaodong Zhang、Runlei Du、Rihui Cao

  DOI：10.1016/j.bmcl.2016.08.084

  日期：2016.10

  A series of novel alkyl diamine linked bivalent beta-carbolines was synthesized and evaluated for antiproliferative activity, inhibition of cell migration and tube formation, and anti-angiogenic activity in vivo. The results showed that most bivalent beta-carbolines displayed significant antiproliferative effect against human umbilical vein cell lines EA.HY926. Compound 2s was found to be the most potent antiproliferative agent with IC50 value of 1.06 mu M against EA.HY926 cell lines. Further investigations on mechanisms of action revealed that compound 2s significantly inhibited EA.HY926 cells migration and tube formation in a dose-dependent manner. Moreover compound 2s exhibited significant angiogenesis inhibitory effects in CAM assay, and the antiangiogenetic potency was comparable with the reference drug Endostar (30 mu M). (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis of novel β-carbolines with efficient DNA-binding capacity and potent cytotoxicity
  作者：Zhiyong Chen、Rihui Cao、Buxi Shi、Wei Yi、Liang Yu、Huacan Song、Zhenhua Ren、Wenlie Peng

  DOI：10.1016/j.bmcl.2010.05.034

  日期：2010.7

  A series of water-soluble beta-carbolines, bearing a flexible amino side chain, was prepared and evaluated in vitro against a panel of human tumor cell lines. The N-9-arylated alkyl substituted beta-carbolines represented the most interesting cytotoxic activities, and compound 7b was found to be the most potent antitumor agent with IC50 values lower than 10 mu M against eight human tumor cell lines. The results confirmed that the N-9-arylated alkyl substituents of beta-carboline nucleus played an important role in the modulation of the cytotoxic potencies. In addition, these compounds were found to exhibit significant DNA-binding affinity. (c) 2010 Published by Elsevier Ltd.