9-isobutyl-1-methyl-β-carboline | 1339940-06-5

• 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-isobutyl-1-methyl-β-carboline
• 英文别名: 1-Methyl-9-(2-methylpropyl)pyrido[3,4-b]indole
• CAS: 1339940-06-5
• 化学式: C₁₆H₁₈N₂
• 分子量: 238.332
• InChiKey: JZVCPYWJKVOHCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-isobutyl-1-methyl-β-carboline 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  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：

  哈尔满碱 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到9-isobutyl-1-methyl-β-carboline
  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

文献信息

• Multicomponent synthesis of novel β-carboline-fused imidazolium derivatives <i>via</i> the Mannich reaction: cytotoxicity, molecular docking, and mechanistic studies as angiogenesis inhibitors
  作者：Siyu Zhu、Xiaofei Chen、Wei Chen、Qin Ma、Meng Li、Wenxi Fan、Jie Zhang、Liang Guo

  DOI：10.1039/d1nj05471f

  日期：——

  In this paper, a novel series of β-carboline-fused imidazolium derivatives (3a–3v) were designed and synthesized based on the structures of fascaplysin and our reported novel compound HMD-272 (9-(3-phenylpropyl)-2-benzyl-β-carbolinium bromide). Evaluation of the cytotoxicity of 3a–3v was conducted using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay in lung carcinoma (A549)

  本文基于 fascaplysin 的结构和我们报道的新型化合物 HMD-272 (9-(3-phenylpropyl) -2 - benzyl -β-溴化碳）。在肺癌 (A549)、胃癌 (BGC-823) 中使用 3-(4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四唑 (MTT) 测定法评估3a-3v的细胞毒性、鼠结肠癌 (CT-26)、肝癌 (Bel-7402) 和乳腺癌 (MCF-7) 细胞系。结果表明，大多数目标化合物对一种或多种癌细胞系表现出优异的活性，化合物3i、3j、3m、3p、3u和3v对测试的肿瘤细胞系表现出最高的细胞毒活性 (IC 50 < 10 μM)。对作用机制的初步研究表明，化合物3v可以以剂量依赖性方式显着抑制EA.HY926细胞管的形成。对初步作用机制的进一步研究表明，化合物3v在鸡绒毛尿囊膜 (CAM) 试验中具有明显的血管生成抑制作用。此外，为了了解化
• New β-carboline derivatives containing imidazolium as potential VEGFR2 inhibitors: synthesis, X-ray structure, antiproliferative evaluations, and molecular modeling
  作者：Ling Ma、Xiaofei Chen、Siyu Zhu、Wei Chen、Qin Ma、Wenxi Fan、Jie Zhang、Liang Guo

  DOI：10.1039/d2md00065b

  日期：——

  A series of new β-carboline derivatives containing an imidazolium moiety were designed and synthesized via the reaction of β-carboline-1-carboxaldehydes, acetyl chloride, primary amine, and formaldehyde. The antitumor activity of the synthesized compounds was examined against lung carcinoma (A549), gastric carcinoma (BGC-823), murine colon carcinoma (CT-26), liver carcinoma (Bel-7402) and breast carcinoma

  通过 β-咔唑-1-甲醛、乙酰氯、伯胺和甲醛的反应，设计合成了一系列含有咪唑鎓部分的新型 β-咔啉衍生物。检测合成化合物对肺癌 （A549） 、胃癌 （BGC-823） 、小鼠结肠癌 （CT-26）、肝癌 （Bel-7402） 和乳腺癌 （MCF-7） 细胞的抗肿瘤活性。结果表明，大多数化合物表现出显着的抗增殖活性，在某些情况下大于顺铂，并且发现化合物 3z 是针对 A549、BGC823、CT-26、Bel-7402 和 MCF-7 细胞系最有效的抗增殖剂，IC50 值为 2.7 ± 0.4、2.7 ± 0.6、2.4 ± 0.2、3.2 ± 0.2 和 5.6 ± 0.3 μM， 分别。结合良好的体外效能，还评估了所选化合物在小鼠中的抗肿瘤疗效。化合物 3z 在肉瘤 180 模型中表现出有效的抗肿瘤活性，肿瘤抑制率为 48.6%。对作用机制的初步研究表明，化合物 3z 可以以剂量依赖性方式显着抑制