1-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole | 6649-95-2

• 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: 1-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 英文别名: 1-(3-Methoxyphenyl)-2,3,4,9-tetrahydro-1H-beta-carboline
• CAS: 6649-95-2
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: LACQLKYZMSEMTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲苯 为溶剂， 以180 mg的产率得到1-(3-methoxyphenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole
  参考文献：
  名称：

  N-溴代琥珀酰亚胺促进了从四氢-β-咔啉合成β-咔啉和3,4-二氢-β-咔啉

  摘要：

  本文中，我们报道了由N-溴琥珀酰亚胺在0°C到室温（rt）的介导下，由N-溴琥珀酰亚胺在四氢-β-咔啉中轻松合成3,4-二氢-β-咔啉和芳香族β-咔啉。中等产量。

  DOI：

  10.1016/j.tetlet.2016.01.081
• 作为产物：
  描述：

  1-(3-methoxyphenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole 在 sodium tetrahydroborate 作用下， 生成 1-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  M4 agonists/5HT7 antagonists with potential as antischizophrenic drugs: Serominic compounds

  摘要：

  Chronic low-dose treatment of rats with the psychomimetic drug, phencyclidine, induces regionally specific metabolic and neurochemical changes in the CNS that mirror those observed in the brains of schizophrenic patients. Recent evidence suggests that drugs targeting serotoninergic and muscarinic receptors, and in particular 5-HT7 antagonists and M-4 agonists, exert beneficial effects in this model of schizophrenia. Compounds that display this combined pattern of activity we refer to as serominic compounds. Based upon leads from natural product screening, we have designed and synthesised such serominic compounds, which are principally arylamidine derivatives of tetrahydroisoquinolines, and shown that they have the required serominic profile in ligand binding assays and show potential antipsychotic activity in functional assays. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.093

文献信息

• Cerium Chloride Catalyzed, 2-Iodoxybenzoic Acid Mediated Oxidative Dehydrogenation of Multiple Heterocycles at Room Temperature
  作者：Santanu Hati、Subhabrata Sen

  DOI：10.1002/ejoc.201601419

  日期：2017.3.3

  Catalytic cerium chloride was found to activate 2-iodoxybenzoic acid (IBX) for the oxidative dehydrogenation of tetrahydroisoquinolines, tetrahydro-β-carbolines, and thiazolidines to their dehydrogenated and aromatic forms at room temperature in moderate to excellent yields. The robustness of the protocol was demonstrated by scaling up the reactions to multigram quantities.

  发现催化氯化铈活化 2-碘氧基苯甲酸 (IBX)，用于在室温下将四氢异喹啉、四氢-β-咔啉和噻唑烷氧化脱氢为其脱氢和芳族形式，产率中等至极好。该协议的稳健性通过将反应放大到数克数量来证明。
• Synthesis and Pharmacological Evaluation of 1,2,3,4-Tetrahydro-.BETA.-carboline Derivatives.
  作者：Yutaka KAWASHIMA、Akiyo HORIGUCHI、Minoru TAGUCHI、Yoshimi TUYUKI、Yasuko KARASAWA、Hiroaki ARAKI、Katsuo HATAYAMA

  DOI：10.1248/cpb.43.783

  日期：——

  A series of 1, 2, 3, 4-tetrahydro-β-carbolines has been synthesized and evaluated for cerebral protecting effects against lipid peroxidation and potassium cyanide intoxication in mice. Most of the compounds synthesized had potent effects against lipid peroxidation. Among them, 1-(3, 5-dimethoxyphenyl)-2-propyl-1, 2, 3, 4-tetrahydro-β-carboline (22) was found to have a combination of potent effects against both lipid peroxidation and potassium cyanide intoxication. Structure-activity relationships are discussed.

  一系列1,2,3,4-四氢-β-咔啉化合物已被合成并评价其对小鼠脂质过氧化和氰化钾中毒的脑保护作用。大多数合成的化合物对脂质过氧化具有强效作用。其中，1-(3,5-二甲氧基苯基)-2-丙基-1,2,3,4-四氢-β-咔啉（22）被发现对脂质过氧化和氰化钾中毒均具有强效组合作用。结构-活性关系在此进行了讨论。
• Asymmetric Biocatalytic Synthesis of 1‐Aryltetrahydro‐β‐carbolines Enabled by “Substrate Walking”
  作者：Elisabeth Eger、Joerg H. Schrittwieser、Dennis Wetzl、Hans Iding、Bernd Kuhn、Wolfgang Kroutil

  DOI：10.1002/chem.202004449

  日期：2020.12.9

  Stereoselective catalysts for the Pictet–Spengler reaction of tryptamines and aldehydes may allow a simple and fast approach to chiral 1‐substituted tetrahydro‐β‐carbolines. Although biocatalysts have previously been employed for the Pictet–Spengler reaction, not a single one accepts benzaldehyde and its substituted derivatives. To address this challenge, a combination of substrate walking and transfer of beneficial

  色胺和醛的 Pictet-Spengler 反应的立体选择性催化剂可能允许简单快速地制备手性 1-取代四氢-β-咔啉。尽管生物催化剂以前曾用于皮克泰-斯宾格勒反应，但没有一种生物催化剂接受苯甲醛及其取代衍生物。为了应对这一挑战，结合底物行走和不同野生型主链之间有益突变的转移，将来自萝芙木( Rs STR) 的胡豆苷合酶开发成适合色胺和苯甲醛不对称 Pictet-Spengler 缩合的酶衍生物。双变体Rs STR V176L/V208A 接受各种邻位、间位和对位取代的苯甲醛，并产生相应的手性 1-芳基-四氢-β-咔啉，对映体过量高达 99%。
• A mild and efficient route to 2-benzyl tryptamine derivatives via ring-opening of β-carbolines
  作者：Fariza Hadjaz、Saïd Yous、Nicolas Lebegue、Pascal Berthelot、Pascal Carato

  DOI：10.1016/j.tet.2008.07.056

  日期：2008.10

  described a mild and easy method, in two steps, by which various benzyl groups were introduced in the C-2 position of tryptamine. The first step consisted on the synthesis of β-carbolines, starting from tryptamine derivatives, by a Pictet–Spengler reaction. Ring-opening of the β-carbolines, by hydrogenation, led to the desired 2-substituted benzyl tryptamine indole products. A supplementary step of alkylation

  我们分两步描述了一种温和而简便的方法，通过该方法，将多种苄基引入色胺的C-2位置。第一步包括通过Pictet-Spengler反应从色胺胺衍生物开始合成β-咔啉。通过氢化使β-咔啉开环，得到所需的2-取代的苄基色胺为吲哚产物。可以实现烷基化的补充步骤，以得到N-烷基-2-取代的苄基色胺。在这些反应过程中，氮原子不需要任何保护步骤。
• Iodine-Catalyzed Metal-Free Oxidative Ring Opening of 1-Aryltetrahydro-β-carbolines: Facile Synthesis of C-2 Aroyl and Aryl Methanimino Indole Derivatives
  作者：Jyoti Chauhan、Tania Luthra、Subhabrata Sen

  DOI：10.1002/ejoc.201800879

  日期：2018.9.16

  C‐2 aroyl and aryl methanimino indole derivatives can be synthesized by catalytic oxidative ring opening of tetrahydro‐β‐carbolines in moderate to excellent yields. The method can be use to synthesize Luzindole, a selective melatonin receptor antagonist and an investigational drug against depression and disruption of the circadian rhythm, on multi‐gram scale.

  可以通过四氢-β-咔啉的催化氧化开环来合成C-2芳酰基和芳基甲基苯胺基吲哚衍生物，产率中等至优异。该方法可用于以克数合成Luzindole，一种选择性的褪黑激素受体拮抗剂和抗抑郁药和昼夜节律紊乱的研究药物。