methyl 1-(naphthalen-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylate | 952201-04-6

• 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: methyl 1-(naphthalen-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: 1-(2-naphthyl)-β-carboline-3-carboxylic acid methyl ester；methyl 1-naphthalen-2-yl-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 952201-04-6
• 化学式: C₂₃H₁₆N₂O₂
• 分子量: 352.392
• InChiKey: HXDHRSKNQSDVPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-(naphthalen-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylate 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (9-Ethyl-1-naphthalen-2-ylpyrido[3,4-b]indol-3-yl)methanol
  参考文献：
  名称：

  Syntheses of novel β-carboline derivatives and the activities against five tumor-cell lines

  摘要：

  A series of beta-carbolines possessing the aryl group at C-1 position has been synthesized from tryptophan. The newly synthesized compounds were screened for their in vitro anticancer activity against various human cancer cell lines by MTT assay. Some of them exhibited anticancer activity with IC50 values lower than 10 mu M outdistanced the cisplatin level. Structure-activity relationship reveals that the alcohol substituents at C-3 position played an important role in inhibition activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.076
• 作为产物：
  描述：

  (S)-1-Naphthalen-2-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 在 三氯异氰尿酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以3.16 g的产率得到methyl 1-(naphthalen-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  β-咔啉的简便高效的一锅法合成

  摘要：

  通过 Pictet-Spengler 反应从色氨酸甲酯 1 和醛 2 初步形成四氢咔啉 3，然后用三氯氰尿酸处理，为以优异的收率一锅法合成 β-咔啉提供了一种简便有效的途径。

  DOI：

  10.1080/00397910903097245

文献信息

• A practical synthesis of β-carbolines by tetra-n-butylammonium bromide (TBAB)-mediated cycloaromatization reaction of aldehydes with tryptophan derivatives
  作者：Zhen Wang、Zhenzhen Yu、Yao Yao、Yakai Zhang、Xuefeng Xiao、Bin Wang

  DOI：10.1016/j.cclet.2019.07.001

  日期：2019.8

  Abstract A mild and efficient nBu4NBr-mediated oxidative cycloaromatization to prepare β-carbolines from readily available tryptophans and aldehydes is described. The reaction is practical and allows the synthesis of β-carbolines on gram-scale. Some of products crystallized from the reaction mixture and were easily removed by filtration, obviating the need for chromatographic separation.

  摘要描述了一种温和而有效的nBu4NBr介导的氧化环芳构化反应，可从易于获得的色氨酸和醛制备β-咔啉。该反应是实用的，并且允许以克规模合成β-咔啉。一些产物从反应混合物中结晶出来，很容易通过过滤除去，从而无需进行色谱分离。
• Facile and Efficient One-Pot Synthesis of β-Carbolines
  作者：Jian-Guo Tang、Han Liu、Zhong-Yu Zhou、Ji-Kai Liu

  DOI：10.1080/00397910903097245

  日期：2010.4.26

  tetrahydrocarboline 3 from tryptophan methyl ester 1 and aldehyde 2 by Pictet–Spengler reaction, followed by treatment with trichlorocyanuric acid, provides a facile and efficient route for a one-pot synthesis of β-carbolines with excellent yields.

  通过 Pictet-Spengler 反应从色氨酸甲酯 1 和醛 2 初步形成四氢咔啉 3，然后用三氯氰尿酸处理，为以优异的收率一锅法合成 β-咔啉提供了一种简便有效的途径。
• New β-carboline derivatives as potential α-glucosidase inhibitor: Synthesis and biological activity evaluation
  作者：Jin Lin、Di Xiao、Li Lu、Bingwen Liang、Zhuang Xiong、Xuetao Xu

  DOI：10.1016/j.molstruc.2023.135279

  日期：2023.7

  find potent α-glucosidase inhibitors, thirty-one β-carboline derivatives containing piperazine moieties (6a∼6u, 7a∼7j) were synthesized and evaluated their α-glucosidase inhibitory activity. Most β-carboline derivatives showed potential α-glucosidase inhibitory activity, especially, compound 7c presented obvious α-glucosidase inhibitory activity (IC50: 8.9 ± 0.2 μM), ∼ 69 folds stronger than acarbose (IC50:

  α-葡萄糖苷酶是糖尿病的重要治疗靶点。为了寻找有效的 α-葡萄糖苷酶抑制剂，合成了31 个含有哌嗪部分的 β-咔啉衍生物 ( 6a∼6u, 7a∼7j ) 并评估了它们的 α-葡萄糖苷酶抑制活性。大多数β-咔啉衍生物表现出潜在的α-葡萄糖苷酶抑制活性，尤其是化合物7c表现出明显的α-葡萄糖苷酶抑制活性（IC 50：8.9 ± 0.2 μM），比阿卡波糖（IC 50：610.7 ± 0.1 μM）强约69倍。抑制机制和动力学解释了化合物7c是一种可逆的混合型抑制剂。采用 CD 光谱、3D 荧光和分子对接揭示7c的机制抗α-葡萄糖苷酶。细胞毒性测定确定了7c的低细胞毒性。
• Syntheses of novel β-carboline derivatives and the activities against five tumor-cell lines
  作者：Bing Bai、Xing-Yao Li、Li Liu、Yan Li、Hua-Jie Zhu

  DOI：10.1016/j.bmcl.2013.11.076

  日期：2014.1

  A series of beta-carbolines possessing the aryl group at C-1 position has been synthesized from tryptophan. The newly synthesized compounds were screened for their in vitro anticancer activity against various human cancer cell lines by MTT assay. Some of them exhibited anticancer activity with IC50 values lower than 10 mu M outdistanced the cisplatin level. Structure-activity relationship reveals that the alcohol substituents at C-3 position played an important role in inhibition activity. (C) 2013 Elsevier Ltd. All rights reserved.
• 10.1021/acs.jmedchem.4c00030
  作者：Zhu, Di、Lu, Yu、Yan, Zhanchao、Deng, Qian、Hu, Bo、Wang, Yinsong、Wang, Wenjing、Wang, Yanming、Wang, Yuji

  DOI：10.1021/acs.jmedchem.4c00030

  日期：——