(S)-1-Naphthalen-2-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester | 865619-26-7

• 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: (S)-1-Naphthalen-2-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• CAS: 865619-26-7
• 化学式: C₂₃H₂₀N₂O₂
• 分子量: 356.424
• InChiKey: RICWOOUOBOCYNQ-BGERDNNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.12
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-1-Naphthalen-2-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-(2'-naphthyl)-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  A β-Carboline Derivate PAD4 Inhibitor Reshapes Neutrophil Phenotype and Improves the Tumor Immune Microenvironment against Triple-Negative Breast Cancer

  摘要：

  DOI：

  10.1021/acs.jmedchem.4c00030
• 作为产物：
  描述：

  L-色氨酸 在 氯化亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 (S)-1-Naphthalen-2-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A β-Carboline Derivate PAD4 Inhibitor Reshapes Neutrophil Phenotype and Improves the Tumor Immune Microenvironment against Triple-Negative Breast Cancer

  摘要：

  DOI：

  10.1021/acs.jmedchem.4c00030

文献信息

• 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。
• Parallel Synthesis of 1,2,3,4-Tetrahydro-β-carbolines Using Microwave Irradiation
  作者：Chung-Ming Sun、Cheng-Yi Wu

  DOI：10.1055/s-2002-34220

  日期：——

  Novel soluble polymer supported synthesis of 1,2,3,4-tetrahydro-β-carboline derivatives in the microwave oven is reported. Commercially available Fmoc-protected tryptophan was directly anchored to MeO-PEG-OH via an ester linkage in the presence of DCC and DMAP. One pot cyclocondensation of polymer-bound tryptophan with a variety of aldehydes and ketones has been carried out under microwave irradiation to provide immobilized 1,2,3,4-tetra-hydro-β-carboline derivatives. The desired products were then liberated from the soluble matrix in good yield and good purity.

  报告了在微波炉中合成 1,2,3,4-四氢-δ-咔啉衍生物的新型可溶性聚合物。在 DCC 和 DMAP 的存在下，市售的 Fmoc 保护色氨酸通过酯键直接锚定到 MeO-PEG-OH 上。在微波辐照下，将聚合物结合的色氨酸与各种醛和酮进行一锅环缩合，从而得到固定的 1,2,3,4-四氢δ-咔啉衍生物。随后，所需的产物以良好的收率和纯度从可溶性基质中释放出来。
• Synthesis of fused tetrahydro-β-carbolinequinoxalinones in 1-n-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide ([bdmim][Tf2N]) and 1-n-butyl-2,3-dimethylimidazolium perfluorobutylsulfonate ([bdmim][PFBuSO3]) ionic liquids
  作者：Ming-Chung Tseng、Yang-Min Liang、Yen-Ho Chu

  DOI：10.1016/j.tetlet.2005.06.153

  日期：2005.9

  Starting from tryptophan methyl ester, a three-step synthesis of fused tetrahydro-beta-carbolinequinoxalinones in two new ionic liquids, [bdmim][Tf2N] and [bdmim][PFBUSO3], was described. Both ionic liquids can be readily prepared from commercially available starting materials in high yields. Unlike the commonly used [PF6]-based ionic liquids that evidently undergo slow hydrolysis of the PF6 anion with the concomitant release of HF, ionic liquids of [bdmim][Tf2N] and [bdmim][PFBuSO3] are not only chemically stable but also apparently inert to hydrolysis and therefore organic reactions carried out in both ionic liquids proceed smoothly with good yields. The overall isolated yields for this three-step synthesis of tetrahydro-beta-carbolinequinoxalinones were 34-55%. To the best of our knowledge, the preparation of fused tetrahydro-beta-carbolinequinoxalinones was unprecedented. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.