9-(3-phenylpropyl)-1-methyl-β-carboline-3-carboxaldehyde | 1256282-52-6

• 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-(3-phenylpropyl)-1-methyl-β-carboline-3-carboxaldehyde
• 英文别名: 1-Methyl-9-(3-phenylpropyl)pyrido[3,4-b]indole-3-carbaldehyde
• CAS: 1256282-52-6
• 化学式: C₂₂H₂₀N₂O
• 分子量: 328.414
• InChiKey: ZPSTXRBPIZSWJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 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-(3-phenylpropyl)-1-methyl-β-carboline-3-carboxaldehyde 在 甲醇 、 sodium cyanoborohydride 作用下， 生成 N,N-bis[(9-(3-propylphenyl)-1-methyl-β-carboline-3-yl)methyl]butane-1,4-diamine
  参考文献：
  名称：

  Bivalent β-Carbolines Inhibit Colorectal Cancer Growth through Inducing Autophagy

  摘要：

  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。

  DOI：

  10.1248/cpb.c21-00588
• 作为产物：
  描述：

  1,2,3,4-四氢哈尔满-3-羧酸 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 、 mineral oil 为溶剂， 反应 20.0h， 生成 9-(3-phenylpropyl)-1-methyl-β-carboline-3-carboxaldehyde
  参考文献：
  名称：

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

  摘要：

  一系列新颖的双价β-咔啉类化合物被合成并评估为有效的血管生成抑制剂。

  DOI：

  10.1039/c6md00360e

文献信息

• Synthesis and Biological Evaluation of Novel .BETA.-Carbolines as Potent Cytotoxic and DNA Intercalating Agents
  作者：Zhiyong Chen、Rihui Cao、Buxi Shi、Wei Yi、Liang Yu、Huacan Song、Zhenhua Ren

  DOI：10.1248/cpb.58.901

  日期：——

  A series of novel water-soluble β-carbolines bearing a flexible amino side chain was designed, synthesized and evaluated as potent cytotoxic and DNA intercatalating agents. The N9-arylated alkyl substituted β-carbolines represented the most interesting cytotoxic activities. The results suggested that (1) the N9-arylated alkyl substituents of β-carboline nucleus played a very important role in the modulation of the cytotoxic potencies; (2) the length of the alkylamino side chain significantly affected their cytotoxic potency, and N,N-dimethylaminopropylamino substituent were more favorable. In addition, these compounds were found to exhibit significant DNA intercalating potencies.

  设计、合成了一系列带有柔性氨基侧链的新型水溶性 β-咔啉，并作为有效的细胞毒性剂和 DNA 嵌入剂进行了评估。 N9-芳基化烷基取代的β-咔啉代表了最有趣的细胞毒性活性。结果表明：（1）β-咔啉核上的N9-芳基化烷基取代基在细胞毒效力的调节中发挥着非常重要的作用； (2)烷基氨基侧链的长度显着影响其细胞毒效力，且N,N-二甲基氨基丙氨基取代基更有利。此外，这些化合物被发现表现出显着的 DNA 嵌入能力。
• 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 and preliminary evaluation of novel alkyl diamine linked bivalent β-carbolines as angiogenesis inhibitors
  作者：Liang Guo、Wei Chen、Wenxi Fan、Qin Ma、Rongqin Sun、Guang Shao、Rihui Cao

  DOI：10.1039/c6md00360e

  日期：——

  A series of novel bivalent β-carbolines were synthesized and evaluated as potent angiogenesis inhibitors.

  一系列新颖的双价β-咔啉类化合物被合成并评估为有效的血管生成抑制剂。
• 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。