9-isopropyl-1-methyl-β-carboline

• 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-isopropyl-1-methyl-β-carboline
• 英文别名: 1-Methyl-9-propan-2-ylpyrido[3,4-b]indole；1-methyl-9-propan-2-ylpyrido[3,4-b]indole
• 化学式: C₁₅H₁₆N₂
• 分子量: 224.305
• InChiKey: XYTNJRXVUXNZRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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-isopropyl-1-methyl-β-carboline 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以53%的产率得到9-isopropyl-β-carboline-1-carboxaldehyde
  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：

  哈尔满碱 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到9-isopropyl-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

• 1位双胺β-咔啉碱类化合物、其制法和其药物 组合物与用途
  申请人：新疆华世丹药物研究有限责任公司

  公开号：CN104177376B

  公开（公告）日：2020-04-10

  本发明公开了1位二胺连接的双β‑咔啉碱类化合物、其制法和其药物组合物与用途。具体而言，所述的双β‑咔啉碱类化合物及其可药用盐如通式II所述，这类双β‑咔啉碱类化合物的制备是通过两分子的β‑咔啉‑1‑甲醛和一分子的二胺NH2(CH2)nNH2、先进行缩合反应，再进行氢化反应制备的。本发明还公开了一种药物组合物，包括有效剂量的式II所示双β‑咔啉碱类化合物和药效学上可接受的载体，以及这类双β‑咔啉碱类化合在制备抗肿瘤药物中的应用，包括黑色素瘤、胃癌、肺癌、乳腺癌、肾癌、肝癌、口腔表皮癌、宫颈癌、卵巢癌、胰腺癌、前列腺癌、结肠癌。