methyl 1-ethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate | 75304-03-9

• 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-ethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: 1-ethyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-β-carboline；1-ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline；1-ethyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• CAS: 75304-03-9
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: ADIHMVQHJFGVMN-UHFFFAOYSA-N

物化性质

• 沸点：
  424.0±45.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-ethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 哌啶 、 [bdmim][PF₆] 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.07h， 生成
  参考文献：
  名称：

  Synthesis of tetrahydro-β-carbolinediketopiperazines in [bdmim][PF6] ionic liquid accelerated by controlled microwave heating

  摘要：

  Because of their negligible vapor pressures and large dipoles, ionic liquids are excellent media for microwave-accelerated organic reactions. Using low-power microwave irradiation in the new [bdmim][PF6] ionic liquid with temperature controlled at 60degreesC, a three-step synthesis (Pictet-Spengler, Schotten-Baumann, and intramolecular ester amidation) of tetraliydro-beta-carboline-diketopiperazines starting from tryptophan methyl ester was achieved with good isolated yields (49-69%) in only 5 min. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.056
• 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 methyl 1-ethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Phytochemical meanings of tetrahydro-β-carboline moiety in strictosidine derivatives

  摘要：

  Synthesis of 13 different tetrahydro-beta-carbolines (THBC) was accomplished by applying the Pictet-Spengler reaction with seven aldehydes, which have been coupled with tryptamine (6) and L-tryptophan methyl ester (7), respectively. The resulting products represent analogues of strictosidine (1) and carboxystrictosidine (5). They were investigated with respect to possible effects on herbivores in feeding bioassays upon the generalist Spodoptera littoralis. Maximum inhibition averages were 42% after four and 46% after six days for the most effective product (19) at 1000 ppm. Additionally, the frass of this particular bioassay was investigated via HPLC-UV for THBC digestion. All synthesized THBCs were also tested for their radical scavenger activity by monitoring their interaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH). Compounds 16-20, 24 and 25 exhibited radical scavenging activity, ranging from 50% to 74% compared to that of a-tocopherol. All results were discussed with respect to possible contributions of tetrahydro-beta-carboline moieties in bioactivities of strictosidine (1) and its biodegradation products. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.028

文献信息

• The Broad Aryl Acid Specificity of the Amide Bond Synthetase McbA Suggests Potential for the Biocatalytic Synthesis of Amides
  作者：Mark Petchey、Anibal Cuetos、Benjamin Rowlinson、Stephanie Dannevald、Amina Frese、Peter W. Sutton、Sarah Lovelock、Richard C. Lloyd、Ian J. S. Fairlamb、Gideon Grogan

  DOI：10.1002/anie.201804592

  日期：2018.9.3

  Amide bond formation is one of the most important reactions in pharmaceutical synthetic chemistry. The development of sustainable methods for amide bond formation, including those that are catalyzed by enzymes, is therefore of significant interest. The ATP‐dependent amide bond synthetase (ABS) enzyme McbA, from Marinactinospora thermotolerans, catalyzes the formation of amides as part of the biosynthetic

  酰胺键的形成是药物合成化学中最重要的反应之一。因此，引起酰胺键形成的可持续方法的发展，包括被酶催化的那些方法，引起了人们的极大兴趣。ATP依赖的酰胺键合成酶（ABS）酶McbA，来自Marinoctinospora thermotolerans，催化酰胺的形成，这是通向玛丽娜咔啉次生代谢物的生物合成途径的一部分。反应通过腺苷酸中间体进行，在一个活性位点内催化了腺苷酸化和酰胺化步骤。在这项研究中，McbA被用于由一系列芳基羧酸与伴侣胺以1-5摩尔当量提供的合成药物型酰胺。McbA的结构揭示了芳酸底物耐受性的结构决定因素以及与催化的两个半反应相关的构象差异。McbA的催化性能以及其结构表明，该酶和其他ABS酶可能经过工程改造，可用于药物相关（手性）酰胺的可持续合成。
• Sodium periodate oxidation of tetrahydro-β-carboline derivatives
  作者：Franco Gatta、Domenico Misiti

  DOI：10.1002/jhet.5570260302

  日期：1989.5

  The oxidation of some 3-(methoxy- and ethoxycarbonyl)tetrahydro-β-carboline derivatives with sodium periodate led to the formation of 1, 4-benzodiazonine derivatives or fully aromatic β-carbolines depending on both nature and number of substituents at 1-position.

  某些3-（甲氧基-和乙氧基羰基）四氢-β-咔啉衍生物与高碘酸钠的氧化作用会导致生成1,4-苯二重氮衍生物或完全芳族的β-咔啉，具体取决于1位上取代基的性质和数量。
• 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。
• Selenium dioxide oxidations in the indole area. Synthesis of β-carboline alkaloids
  作者：M. Cain、O. Campos、F. Guzman、J. M. Cook

  DOI：10.1021/ja00342a045

  日期：1983.2
• Campos, Olivia; DiPierro, Mike; Cain, Michael, Heterocycles, 1980, vol. 14, # 7, p. 975 - 984
  作者：Campos, Olivia、DiPierro, Mike、Cain, Michael、Mantei, Robert、Gawish, Ali、Cook, James M.

  DOI：——

  日期：——